cas 334-88-3, Diazomethane | Articles data

Articles about 334-88-3Total 231 be found

Article title
Article abstract
Author
Journal number and time
Download

Synthesis of conformationally restricted glutamic acid analogs based on the spiro[3.3]heptane scaffold
A library of isomeric glutamic acid analogs based on the spiro[3.3]heptane skeleton is designed. Two members of the library, (R)- and (S)-2-amino-spiro[3.3]heptane-2,6-dicarboxylic acid hydrochlorides, were synthesized. The stereochemistry of the synthesi
Radchenko, Dmytro S.,Grygorenko, Oleksandr O.,Komarov, Igor V.
p. 2924 - 2930
(2008)
Read Online

AUTOMATED DIAZOMETHANE GENERATOR, REACTOR AND SOLID PHASE QUENCHER
An automated apparatus (Diazo-M-pen and Diazo-M-cube) for production, utilization and quenching of highly toxic diazomethane comprising of integrated pumps, tubular flow reactor, liquid-liquid micro-separator, solid MOF quencher etc.
-
Page/Page column 9-10; 14

(2022/03/09)

A simple method of synthesis of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl and preparation of reduction-resistant spin labels and probes of pyrrolidine series
Stable free radicals are widely used as molecular probes and labels in various biophysical and biomedical research applications of magnetic resonance spectroscopy and imaging. Among these radicals, sterically shielded nitroxides of pyrrolidine series demonstrate the highest stability in biological systems. Here, we suggest new convenient procedure for preparation of 3-carboxy-2,2,5,5-tetraethylpyrrolidine-1-oxyl, a reduction-resistant analog of widely used carboxy-Proxyl, from cheap commercially available reagents with the yield exceeding the most optimistic literature data. Several new spin labels and probes of 2,2,5,5-tetraethylpyrrolidine-1-oxyl series were prepared and reduction of these radicals in ascorbate solutions, mice blood and tissue homogenates was studied.
Dobrynin, Sergey A.,Usatov, Mikhail S.,Zhurko, Irina F.,Morozov, Denis A.,Polienko, Yuliya F.,Glazachev, Yurii I.,Parkhomenko, Dmitriy A.,Tyumentsev, Mikhail A.,Gatilov, Yuri V.,Chernyak, Elena I.,Bagryanskaya, Elena G.,Kirilyuk, Igor A.
(2021/09/28)

Scalable On-Demand Production of Purified Diazomethane Suitable for Sensitive Catalytic Reactions
We have developed a convenient development-scale reactor (0.44 mol/h) to prepare diazomethane from N-methyl-N-nitroso-p-toluenesulfonamide (MNTS) in ～80% yield. Diazomethane (CH2N2) made with this reactor is extracted into nitrogen gas from the liquid reaction mixture, effectively removing it from reagents and byproducts that may interfere in subsequent reactions. Vertically oriented tubular reactors were used to produce and consume diazomethane in situ. Key features of this reactor include high productivity and correspondingly low reactor volume (reactor volume/liquid flow rate = 6.5 min) and a commercially available gas/liquid separator equipped with a selectively permeating hydrophilic membrane. The design of the reactor keeps the inventory below 53 mg of CH2N2 during normal operation. The reactor was demonstrated by generating CH2N2 that was used in a connected continuous reactor. We evaluated esterification reactions and a continuous Pd-catalyzed cyclopropanation reaction with the reactor and achieved high conversion with 1.5 and 4.1 equiv of MNTS precursor, respectively.
Sheeran, Jillian W.,Campbell, Kiersten,Breen, Christopher P.,Hummel, Gerald,Huang, Changfeng,Datta, Anamika,Boyer, Serge H.,Hecker, Scott J.,Bio, Matthew M.,Fang, Yuan-Qing,Ford, David D.,Russell, M. Grace
supporting information
p. 522 - 528
(2021/02/03)

Biological evaluation of 3-benzylidenechromanones and their spiropyrazolines-based analogues
A series of 3-benzylidenechrmanones 1, 3, 5, 7, 9 and their spiropyrazoline analogues 2, 4, 6, 8, 10 were synthesized. X-ray analysis confirms that compounds 2 and 8 crystallize in a monoclinic system in P21/n space groups with one and three molecules in each asymmetric unit. The crystal lattice of the analyzed compounds is enhanced by hydrogen bonds. The primary aim of the study was to evaluate the anti-proliferative potential of 3-benzylidenechromanones and their spiropyrazoline analogues towards four cancer cell lines. Our results indicate that parent compounds 1 and 9 with a phenyl ring at C2 have lower cytotoxic activity against cancer cell lines than their spiropyrazolines analogues. Analysis of IC50 values showed that the compounds 3 and 7 exhibited higher cytotoxic activity against cancer cells, being more active than the reference compound (4-chromanone or quercetin). The results of this study indicate that the incorporation of a pyrazoline ring into the 3-arylideneflavanone results in an improvement of the compounds’ activity and therefore it may be of use in the search of new anticancer agents. Further analysis allowed us to demonstrate the compounds to have a strong inhibitory effect on the cell cycle. For instance, compounds 2, 10 induced 60% of HL-60 cells to be arrested in G2/M phase. Using a DNA-cleavage protection assay we also demonstrated that tested compounds interact with DNA. All compounds at the concentrations corresponding to cytotoxic properties are not toxic towards red blood cells, and do not contribute to hemolysis of RBCs.
Adamus-Grabicka, Angelika A.,Budzisz, Elzbieta,Cieslak, Marcin,Hikisz, Pawe?,Królewska-Golinska, Karolina,Kusz, Joachim,Ma?ecka, Magdalena,Markowicz-Piasecka, Magdalena
(2020/04/10)

The reagent Et2AlX/CH2N2 in cyclopropanation of sterically hindered olefins, as well as oxygen- and nitrogen-containing unsaturated compounds
A transition-metal-free method of cyclopropanation of sterically hindered olefins, substituted allylic alcohols, allylamines, and vinyl silyl ethers was developed using diazomethane in the presence of organic aluminum halides.
Ramazanov,Yaroslavova,Yaubasarov,Gil’manova,Dzhemilev
p. 1869 - 1873
(2019/10/22)

Discovery of Vilaprisan (BAY 1002670): A Highly Potent and Selective Progesterone Receptor Modulator Optimized for Gynecologic Therapies
Progesterone plays an important role in the female reproductive system. However, there is also evidence that gynecologic disorders/diseases such as uterine fibroids and endometriosis are progesterone-dependent. Steroidal and non-steroidal selective progesterone receptor modulators (SPRMs) have shown potential for the treatment of such diseases. Steroidal SPRMs, including mifepristone and ulipristal acetate, have proven effective in clinical trials. However, several steroidal SPRMs containing a dimethylamino substituent have been associated with elevated liver enzymes in patients. An earlier drug discovery program identified lonaprisan as a highly selective SPRM that did not show drug-related change in liver enzyme activity. Building on data obtained from that work, here we describe the research program that culminated in the discovery of a novel steroidal SPRM, vilaprisan, which combines an extremely high potency with very favorable drug metabolism and pharmacokinetic properties. Vilaprisan has entered clinical development and is currently undergoing phase 3 clinical trials.
M?ller, Carsten,Bone, Wilhelm,Cleve, Arwed,Klar, Ulrich,Rotgeri, Andrea,Rottmann, Antje,Schultze-Mosgau, Marcus-Hillert,Wagenfeld, Andrea,Schwede, Wolfgang
supporting information
p. 2271 - 2280
(2018/11/21)

Method for preparing cycloheptanone from cyclohexanone through one step
A method for preparing cycloheptanone from cyclohexanone through one step comprises the following steps: using diazomethane as a reagent to prepare a saturated low alcohol solution, adding cyclohexanone and a diluted acid catalyst to a diazomethane alcohol solution, carrying out a slow addition ring expansion reaction at 10-50 DEG C, and carrying out water vapor distillation to prepare crude cycloheptanone; and rectifying the crude cycloheptanone to obtain cycloheptanone. A saturated C4 or less low alcohol solution of diazomethane is prepared through the following steps: reacting hydrochloric acid with a methylamine solution, adding urea, adding a saturated sodium carbonate solution, carrying out a refluxing reaction, adding diluted sulfuric acid, reacting sulfuric acid with a sodium nitrite solution, adding a strong alkali solution to generate a diazomethane gas, introducing the diazomethane gas to a cooled receiving bottle provided with the C4 or less low alcohol. The method has the advantages of short synthetic route, simplicity in operation, environmental protection, high product yield, substantial reduction of the cost, and high facilitation of industrial production.
-
Paragraph 0014; 0017; 0020

(2017/03/08)

Synthesis of carbazole analogs via Grob fragmentation of norbornyl α-diketones
A regioselective synthesis of carbazole analogs belonging to both the categories of natural origin, viz., microorganisms and higher plant source is reported. The synthesis of carbazole derivatives possessing a methylester group at C-1 position has been ac
Sravanthi, Kadavergu,Agrawal, Sumit Kumar,Rao, Chintada Nageswara,Khan, Faiz Ahmed
supporting information
p. 3449 - 3452
(2016/07/18)

Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives
A series of eighteen quinones and structurally-related oxiranes were synthesized and evaluated for in vitro inhibitory activity against the chloroquine-sensitive 3D7 clone of the human malaria parasite Plasmodium falciparum. 2-amino and 2-allyloxynaphthoquinones exhibited important antiplasmodial activity (median inhibitory concentrations (IC50) 10 μM). Oxiranes 6 and 25, prepared respectively by reaction of α-lapachone and tetrachloro-p-quinone with diazomethane in a mixture of ether and ethanol, exhibited the highest antiplasmodial activity and low cytotoxicity against human fibroblasts (MCR-5 cell line). The active compounds could represent a good prototype for an antimalarial lead molecule.
Carneiro, Paula F.,Pinto, Maria C.R.F.,Marra, Roberta K.F.,Da Silva, Fernando De C.,Resende, Jackson A.L.C.,Rocha E Silva, Luiz F.,Alves, Hilkem G.,Barbosa, Gleyce S.,De Vasconcellos, Marne C.,Lima, Emerson S.,Pohlit, Adrian M.,Ferreira, Vitor F.
p. 134 - 140
(2015/12/04)

Synthesis of cyclopropanated [2.2.1] heterobicycloalkenes: An improved procedure
A safer and improved method to our previous report on palladium-catalyzed cyclopropanation of heterobicyclic alkenes has been developed. By using tetrahydrofuran as the solvent and a more dilute aqueous NaOH solution for the generation of diazomethane fro
Carlson, Emily,Duret, Guillaume,Blanchard, Nicolas,Tam, William
p. 55 - 62
(2016/01/09)

Highly Stereoselective Synthesis of Fluoroalkene Dipeptides via the Novel Chromium(II)-Mediated Carbon-Fluorine Bond Cleavage/New Carbon-Carbon Bond Formation
An efficient chromium(II)-mediated reductive coupling reaction of various CBrF2-containing molecules and aldehydes has been developed. This reaction proceeds presumably via the monofluorinated dichromium(III) intermediate generated by the carbon-fluorine bond activation, and provides a general and straightforward access to synthesize a variety of (E)- or (Z)-β-fluoroallylic alcohols in a highly stereoselective manner. Based on the novel reductive coupling, four types of fluoroalkene dipeptide analogues could be stereoselectively prepared.
Nihei, Takashi,Nishi, Yuji,Ikeda, Natsumi,Yokotani, Saya,Ishihara, Takashi,Arimitsu, Satoru,Konno, Tsutomu
p. 865 - 881
(2016/03/12)

Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step
Acacetin and resveratrol 3,5-di-O-β-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules.
Hanamura, Shun,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi
p. 19 - 26
(2016/03/30)

Inhibition of bacterial biofilms and microbial growth with imidazole derivatives
Disclosure is provided for imidazole derivative compounds useful to inhibit the formation of biofilms and/or inhibit microbial growth, compositions including these compounds, devices including these compounds, and methods of using the same.
-
Page/Page column 40; 41

(2016/04/26)

Second generation modifiers of colistin resistance show enhanced activity and lower inherent toxicity
We recently reported a 2-aminoimidazole-based antibiotic adjuvant that reverses colistin resistance in two species of Gram-negative bacteria. Mechanistic studies in Acinetobacter baumannii demonstrated that this compound downregulated the PmrAB two-compon
Brackett, Christopher M.,Furlani, Robert E.,Anderson, Ryan G.,Krishnamurthy, Aparna,Melander, Roberta J.,Moskowitz, Samuel M.,Ernst, Robert K.,Melander, Christian
supporting information
p. 3549 - 3553
(2016/07/06)

Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor
The efficient synthesis of cyclopropyl boronic esters in library format using a diazomethane flow reactor has been achieved. A pivotal component of the system is a fully automated tube-in-tube reactor allowing for safe handling of hazardous diazomethane on repeated small scale and for the generation of larger quantities of product. The setup enables the repeated execution of Pd-catalyzed cyclopropanation reactions without compromising its operation over time.
Koolman, Hannes F.,Kantor, Stanislaw,Bogdan, Andrew R.,Wang, Ying,Pan, Jeffrey Y.,Djuric, Stevan W.
supporting information
p. 6591 - 6595
(2016/07/16)

Synthesis of Cyclopropanated 7-Azabenzonorbornadienes
7-Azabenzonorbornadienes bearing various aryl or N-substituents were treated with diazomethane in the presence of palladium to afford desirable yields of cyclopropanated products (75-98%). The current approach suggests an efficient synthesis for CH2-cyclopropanated 7-azabenzonorbornadienes which lends promise to the development of new ring-opening preparations of biologically useful organic frameworks.
Carlson, Emily,Tam, William
p. 2449 - 2454
(2016/07/28)

Design and Discovery of Functionally Selective Serotonin 2C (5-HT2C) Receptor Agonists
On the basis of the structural similarity of our previous 5-HT2C agonists with the melatonin receptor agonist tasimelteon and the putative biological cross-talk between serotonergic and melatonergic systems, a series of new (2,3-dihydro)benzofu
Cheng, Jianjun,McCorvy, John D.,Giguere, Patrick M.,Zhu, Hu,Kenakin, Terry,Roth, Bryan L.,Kozikowski, Alan P.
supporting information
p. 9866 - 9880
(2016/11/19)

METHOD FOR THE PREPARATION OF DIAZOALKANES
The present invention relates to a method of forming diazoalkanes. One aspect of the present invention provides a method for the production of a N-alkyl-N-nitroso compound from a starting material, comprising the use of a tribasic acid to acidify an amine. A second aspect of the present invention provides a method for the production of a diazoalkane, comprising reacting a N-alkyl-N-nitroso compound with a base and a phase transfer catalyst, wherein no organic solvent is used.
-
Paragraph 0075-0085

(2015/02/19)

Stereoselective synthesis of cis-2,6-disubstituted morpholines and 1,4-oxathianes by intramolecular reductive etherification of 1,5-diketones
A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6- disubstituted morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural products (±)-chelonin A and formal total synthesis of (±)-chelonin C.
Gharpure, Santosh J.,Anuradha, Dandela,Prasad, Jonnalagadda V. K.,Rao, Pidugu Srinivasa
supporting information
p. 86 - 90
(2015/01/16)

Concise synthesis of alkaloid (-)-205B
Described herein is a short total synthesis of alkaloid (-)-205B (1) by means of an anti-selective SN2 alkylation of an attractively functionalized cyclopropanol and diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation. The synthesis features a general route to cis- or trans-2,6-disubstituted piperidines by lithium aluminum hydride reduction of the imine intermediate by an appropriate choice of solvent and cis- or trans-2,5-disubstituted pyrrolidines by an exceptional level of chirality transfer from a pendant allene. Particularly noteworthy are the brevity and convergence made possible by a segment-coupling strategy.
Rao, Nagavaram Narsimha,Cha, Jin Kun
supporting information
p. 2243 - 2246
(2015/03/04)

Cationic mixed micelles as reaction medium for hydrolysis reactions
The influence of cationic mixed micelles composed of quartenary ammonium surfactants on hydrolysis reactions has been studied in detail. The basic hydrolysis of N-methyl-N-nitroso-p-toluene sulphonamide has been chosen as the reaction probe, while mixed micelles composed of lauryl trimethyl ammonium chloride and octadecyl trimethyl ammonium chloride with different molar ratios were studied as the reaction medium. The ion-exchange pseudophase model was used to fit the experimental results to obtain the kinetic and thermodynamic parameters of the reaction. The result show that the hydrophobic character of the mixed micelles drives the association of the substrate to them, leading to a local increase of reactant concentrations at the micellar interface and, therefore, to a catalytic effect. By tuning the molar ratio of the mixed micelles it is possible to control substrate binding affinity and thus the catalytic efficiency of the reaction medium.
Fernández, Isabel,Pérez-Juste, Jorge,Hervés, Pablo
p. 1866 - 1874
(2015/10/12)

First enantiospecific syntheses of marine merosesquiterpenes neopetrosiquinones A and B: Evaluation of biological activity
The first enantiospecific syntheses of neopetrosiquinones A (6) and B (7), two merosesquiterpenes isolated from the deep-water sponge Neopetrosia cf. proxima, from the labdane diterpene trans-communic acid (10) have been achieved. A key step of the synthetic sequence is the simultaneous aromatization of the C ring and the benzylic oxidation on C-7 of an advanced intermediate, mediated by the oxygen-DDQ system. The in vitro antiproliferative activities of neopetrosiquinone B (7) and of the synthetic intermediates 8 and 9 against human breast (MCF-7), lung (A-549), and colon (T-84) tumor cell lines have been assayed. The most potent was compound 9 (IC50 = 4.1 μM), which was twice as active as natural compound 7 (IC50 = 8.3 μM) against A-549 cells. In addition, the treatment with these compounds resulted in an induction of apoptosis. These findings indicate that the terpene benzoquinones reported here might be potentially useful as anticancer agents.
Chayboun, Ikram,Boulifa, Ettahir,Mansour, Ahmed Ibn,Rodriguez-Serrano, Fernando,Carrasco, Esther,Alvarez, Pablo Juan,Chahboun, Rachid,Alvarez-Manzaneda, Enrique
p. 1026 - 1036
(2015/06/02)

P2X4 RECEPTOR MODULATING COMPOUNDS AND METHODS OF USE THEREOF
Provided herein are P2X4 receptor modulating compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, including but not limited to, chronic pain, neuropathy, inflammatory diseases and central nervous system disorders.
-
Paragraph 00211

(2015/06/25)

BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS
β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.
-
Paragraph 0545; 0546; 0594

(2015/09/22)

Synthesis of halo-substituted framework derivatives of quinopimaric acid
6-Chloro-, 6-chloroacetoxy-, and 16-(2-bromoacetyl)framework derivatives were synthesized from a photoadduct of quinopimaric acid.
Vafina,Uzbekov,Galin,Yunusov
p. 1035 - 1038
(2014/03/21)

Stereoselective synthesis of quaternary carbons via the dianionic Ireland-Claisen rearrangement
A dianionic Ireland-Claisen rearrangement of chiral, nonracemic α-methyl-β-hydroxy allylic esters has been developed that proceeds with high diastereoselectivity and provides products containing three contiguous stereogenic carbons, including a quaternary center. The potential utility of the rearrangement for complex molecule synthesis is also demonstrated.
Crimmins, Michael T.,Knight, John D.,Williams, Philip S.,Zhang, Yan
supporting information
p. 2458 - 2461
(2014/05/20)

A formal synthesis of herboxidiene/GEX1A
A formal synthesis of herboxidiene/GEX 1A is described. This approach demonstrates successful application of the Prins cyclization for the construction of the tetrahydropyran core of the target molecule. The chirality of the side chain has been established through the Sharpless asymmetric dihydroxylation and Evan's alkylation. The olefin cross-metathesis was applied to couple both key fragments. Copyright
Yadav, Jhillu S.,Reddy, G. Madhusudhan,Anjum, S. Rehana,Reddy, B. V. Subba
p. 4389 - 4397
(2014/07/21)

Novel transformation of ethyl cyano(dinitro)acetate in the reactions with diazomethane and diazoethane
-
Tyrkov,Yurtaeva
p. 902 - 903
(2014/08/18)

ω-alkynyl lipid surrogates for polyunsaturated fatty acids: Free radical and enzymatic oxidations
Lipid and lipid metabolite profiling are important parameters in understanding the pathogenesis of many diseases. Alkynylated polyunsaturated fatty acids are potentially useful probes for tracking the fate of fatty acid metabolites. The nonenzymatic and enzymatic oxidations of ω-alkynyl linoleic acid and ω-alkynyl arachidonic acid were compared to that of linoleic and arachidonic acid. There was no detectable difference in the primary products of nonenzymatic oxidation, which comprised cis,trans-hydroxy fatty acids. Similar hydroxy fatty acid products were formed when ω-alkynyl linoleic acid and ω-alkynyl arachidonic acid were reacted with lipoxygenase enzymes that introduce oxygen at different positions in the carbon chains. The rates of oxidation of ω-alkynylated fatty acids were reduced compared to those of the natural fatty acids. Cyclooxygenase-1 and -2 did not oxidize alkynyl linoleic but efficiently oxidized alkynyl arachidonic acid. The products were identified as alkynyl 11-hydroxy-eicosatetraenoic acid, alkynyl 11-hydroxy-8,9-epoxy-eicosatrienoic acid, and alkynyl prostaglandins. This deviation from the metabolic profile of arachidonic acid may limit the utility of alkynyl arachidonic acid in the tracking of cyclooxygenase-based lipid oxidation. The formation of alkynyl 11-hydroxy-8,9-epoxy-eicosatrienoic acid compared to alkynyl prostaglandins suggests that the ω-alkyne group causes a conformational change in the fatty acid bound to the enzyme, which reduces the efficiency of cyclization of dioxalanyl intermediates to endoperoxide intermediates. Overall, ω-alkynyl linoleic acid and ω-alkynyl arachidonic acid appear to be metabolically competent surrogates for tracking the fate of polyunsaturated fatty acids when looking at models involving autoxidation and oxidation by lipoxygenases.
Beavers, William N.,Serwa, Remigiusz,Shimozu, Yuki,Tallman, Keri A.,Vaught, Melissa,Dalvie, Esha D.,Marnett, Lawrence J.,Porter, Ned A.
p. 11529 - 11539
(2014/10/15)

SPIRO AZETIDINE ISOXAZOLE DERIVATIVES AND THEIR USE AS SSTR5 ANTAGONISTS
Provided is a compound represented by the following formula (1) or a salt thereof, which has an SSTR5 antagonistic action: wherein each symbol has the same definition as in the specification.
-
Paragraph 1184

(2014/09/29)

Syntheses of spiroindole melatonin analogues via 2-(indolin-3-ylidene)acetonitrile cycloadditions
2-(2-Oxo-1,2-dihydro-3H-indol-3-ylidene)acetonitriles were subjected to cycloaddition reactions at the double bond affording spiroindole melatonin analogues.
Lozinskaya, Natalia A.,Volkova, Maria S.,Seliverstov, Michael Yu.,Temnov, Victor V.,Sosonyuk, Sergey E.,Proskurnina, Marina V.,Zefirov, Nikolai S.
supporting information
p. 260 - 261
(2015/02/02)

PDE 10a Inhibitors for the Treatment of Type II Diabetes
Disclosed are compounds, compositions and methods for treating Type II diabetes. Such compounds are represented by Formula (I) as follows: wherein R1, R2, L, and Q are defined herein.
-
Paragraph 0927; 0928

(2015/01/06)

2 SUBSTITUTED CEPHEM COMPOUNDS
The compounds of formula (I) of the subject invention are related to 2-substituted cephem compounds, which have a wide antimicrobial spectrum, in particular exhibit potent antimicrobial activity against beta-lactamase producing Gram negative bacteria, and pharmaceutical compositions comprising the same.
-
Paragraph 0292

(2014/05/24)

Antiparasitic activity of natural and semi-synthetic tirucallane triterpenoids from Schinus terebinthifolius (anacardiaceae): Structure/activity relationships
Leishmaniasis and Chagas are diseases caused by parasitic protozoans that affect the poorest population in the World, causing a high mortality and morbidity. As a result of highly toxic and long-term treatments, the discovery of novel, safe and more efficacious drugs is essential. In this work, the in vitro antiparasitic activity and mammalian cytotoxicity of three natural tirucallane triterpenoids, isolated from leaves of Schinus terebinthifolius (Anacardiaceae), and nine semi-synthetic derivatives were investigated against Leishmania (L.) infantum and Trypanosoma cruzi. Trypomastigotes of T. cruzi were the most susceptible parasites and seven compounds demonstrated a trypanocidal activity with IC50 values in the range between 15 and 58 μg/mL. Four compounds demonstrated selectivity towards the intracellular amastigotes of Leishmania, with IC50 values in the range between 28 and 97 μg/mL. The complete characterization of triterpenoids was afforded after thorough analysis of nuclear magnetic resonance (NMR) data as well as electrospray ionization mass spectrometry (ESI-MS). Additionally, structure-activity relationships were performed using Decision Trees.
Morais, Thiago R.,Da Costa-Silva, Thais A.,Tempone, Andre G.,Borborema, Samanta Etel T.,Scotti, Marcus T.,De Sousa, Raquel Maria F.,Araujo, Ana Carolina C.,De Oliveira, Alberto,De Morais, Sergio Antonio L.,Sartorelli, Patricia,Lago, Joao Henrique G.
p. 5761 - 5776
(2014/06/10)

Tranylcypromine substituted cis -hydroxycyclobutylnaphthamides as potent and selective dopamine D3 receptor antagonists
We report a class of potent and selective dopamine D3 receptor antagonists based upon tranylcypromine. Although tranylcypromine has a low affinity for the rat D3 receptor (Ki = 12.8 μM), our efforts have yielded (1R,2S)-11 (CJ-1882), which has Ki values of 2.7 and 2.8 nM at the rat and human dopamine D3 receptors, respectively, and displays respective selectivities of >10000-fold and 223-fold over the rat and human D2 receptors. Evaluation in a β-arrestin functional assay showed that (1R,2S)-11 is a potent and competitive antagonist at the human D3 receptor.
Chen, Jianyong,Levant, Beth,Jiang, Cheng,Keck, Thomas M.,Newman, Amy Hauck,Wang, Shaomeng
supporting information
p. 4962 - 4968
(2014/07/07)

Synthesis of Cyclopropanated 7-Oxabenzonorbornadienes
Symmetrical and unsymmetrical 7-oxabenzonorbornadienes have been cyclopropanated using diazomethane gas under palladium catalysis. Good to excellent isolated yields (64-96%) of cyclopropanated oxabenzonorbornadienes were obtained, and excellent stereoselectivities were observed with exo-cyclopropanes as the only stereoisomeric products. Georg Thieme Verlag Stuttgart New York.
McKee, Mary,Haner, Jamie,Carlson, Emily,Tam, William
p. 1518 - 1524
(2014/06/10)

Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation
A fully continuous four step process for the preparation of β-amino acids from their corresponding α-amino acids utilizing the Arndt-Eistert homologation approach is described. the Partner Organisations 2014.
Pinho, Vagner D.,Gutmann, Bernhard,Kappe, C. Oliver
p. 37419 - 37422
(2014/12/09)

Synthetic studies on strictamine: Unexpected oxidation of tertiary amine in Ru-catalyzed ring-closing olefin metathesis
During synthetic studies toward strictamine, unexpected oxidation of tertiary amine to enamine was observed in ring-closing olefin metathesis (RCM) using Hoveyda-Grubbs 2nd catalyst. Control experiments under deoxygenated conditions indicated Ru-catalyst
Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi
p. 377 - 380
(2013/02/25)

Synthesis and anti-cancer activity of some novel C-17 analogs of ursolic and oleanolic acids
A series of seventeen novel analogs of ursolic and oleanolic acid were synthesized (60-98 %), and evaluated for their anti-cancer potential against a panel of eight human cancer cell lines. Compounds (3-10) showed comparable or better activities than their respective parent compounds against SiHa and HeLa (Cervix), A-549 (Lung), and IMR-32 (Neuroblastoma) cancer cell lines. Significantly, among the bromoalkyl esters (11-19), compound 13 showed promising anti-cancer activity against Leukemia THP-1 cell line at 10 μM concentration. In this series, it is interesting to note that the increase in chain length has an adverse effect on the activity.
Mallavadhani, Uppuluri V.,Mahapatra, Anita,Pattnaik, Banita,Vanga, Nagireddy,Suri, Nitasha,Saxena, Ajit K.
p. 1263 - 1269
(2013/04/10)

Stereoselective total synthesis of (-)-batzellasides a, b, and c
Total synthesis of (-)-L-batzellasides A, B, and C has been achieved in 13 steps from known lactone 2 in 12.6, 13.2, and 13.8 % overall yields, respectively. The key steps in this synthesis were the stereoselective introduction of an allyl group at the C1
Okaki, Toru,Fujimura, Ryohei,Sekiguchi, Masataka,Zhou, Dejun,Sugimoto, Kenji,Minato, Daishiro,Matsuya, Yuji,Kato, Atsushi,Adachi, Isao,Tezuka, Yasuhiro,Saporito, Ralph A.,Toyooka, Naoki
p. 2841 - 2848
(2013/07/11)

Functionally substituted Schiff bases in reduction reactions
Functionally substituted Schiff bases obtained by the condensation of nitroaniline, pyrimidinylaminoaniline, 5-aminoquinoline, 5-aminoquinaldine derivatives with 4-methylformylbenzoate were studied in the reactions of sodium borohydride with acidic activators, hydrazine hydrate in the presence of Raney nickel, Raney alloy in the presence of potassium hydroxide. By the reduction of azomethines new benzyl derivatives of aniline, quinolylamine, arylaminopyrimidine, and phenylenediamine were obtained.
Koroleva,Gusak,Ignatovich,Ermolinskaya
p. 212 - 220
(2013/07/25)

Chemoenzymatic preparation of (6R)-5,6-dihydro-2H-pyran-2-one: A ubiquitous structural motif of biologically active lactones
A chemoenzymatic synthesis of an enantiopure 6-substituted 5,6-dihydro-2H-pyran-2-one using bromobenzene as a starting material is presented. This important structural motif is found in a large number of chiral lactones that present a wide range of biological activities. The key features of the preparation include enzymatic dioxygenation of bromobenzene using Escherichia coli JM109 (pDTG601), microwave-assisted acyloin cleavage, and tin mediated lactonization. The stereochemical assignment for the alcohol was confirmed by NMR analysis of Moshers derivatives.
Carrera, Ignacio,Brovetto, Margarita,Seoane, Gustavo A.
p. 1467 - 1472
(2013/12/04)

COMPLEMENT PATHWAY MODULATORS AND USES THEREOF
The present invention provides a compound of formula I a method for manufacturing the compounds of the invention, and its therapeutic uses as inhibitor of the complement alternative pathway and particularly as inhibitor of Factor B for the treatment of e.g. age-related macular degeneration and diabetic retinopathy. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
-
Page/Page column 87

(2014/01/09)

Synthesis of new N-(arylcyclopropyl)acetamides and N-(arylvinyl)acetamides as conformationally-restricted ligands for melatonin receptors
N-(Arylcyclopropyl)acetamides and N-(arylvinyl)acetamides or methyl ureas have been prepared as constrained analogues of melatonin. The affinity of these new compounds for chicken brain melatonin receptors and recombinant human MT1 and MT2 receptors was evaluated using 2-[ 125I]-iodomelatonin as radioligand. Strict ethylenic or cyclopropyl analogues of the commercialized agonist agomelatine (Valdoxan) were equipotent to agomelatine in binding bioassays. However, the ethylenic analogue was more effective than the cyclopropyl one in the melanophore aggregation bioassay, but was still less potent than the disubstituted 2,7-dimethoxy- naphtalenic compounds.
Morellato, Laurence,Lefas-Le Gall, Marie,Langlois, Michel,Caignard, Daniel-Henri,Renard, Pierre,Delagrange, Philippe,Mathe-Allainmat, Monique
supporting information
p. 430 - 434
(2013/02/23)

3-Trimethylsilylcyclobutylidene. the γ-effect of silicon on carbenes
3-Trimethylsilylcyclobutylidene was generated by pyrolysis of the sodium salt of the tosylhydrazone derivative of 3-trimethylsilylcyclobutanone. This carbene converts to 1-trimethylsilylbicyclobutane as the major product. A labeling study shows that this intramolecular rearrangement product comes from 1,3-hydrogen migration to the carbenic center and not 1,3-silyl migration. Computational studies show two carbene minimum energy conformations, with the lower energy conformation displaying a large stabilizing interaction of the carbene center with the rear lobe of the C3-Si bond. In this conformation, the trimethylsilyl group cannot migrate to the carbene center, and the most favorable process is 1,3-hydrogen migration. When the carbene is generated photochemically in methanol, it reacts by a protonation mechanism giving the highly stabilized 3-trimethylsilylcyclobutyl carbocation as an intermediate. When generated in dimethylamine as solvent, the carbene undergoes preferred attack of this nucleophilic solvent from the back of this C-Si rear lobe stabilized carbene.
Creary, Xavier
p. 6570 - 6578
(2013/06/26)

Perfluoro-tert-butyl-homoserine as a sensitive 19F NMR reporter for peptide-membrane interactions in solution
Fluorine (19F) NMR is a valuable tool for studying dynamic biological processes. However, increasing the sensitivity of fluorinated reporter molecules is a key to reducing acquisition times and accessing transient biological interactions. Here,
Buer, Benjamin C.,Levin, Benjamin J.,Marsh, E. Neil G.
p. 308 - 314
(2013/07/05)

Cycloalkane carboxylic acid derivatives as CXCR3 receptor antagonists
The present invention relates to compounds of formula 1 that are useful as an active ingredient of a medicament for preventive and/or therapeutic treatment of diseases caused by abnormal activation of CXCR3 chemokines. The invention relates furthermore to a process for the preparation of said compounds, to pharmaceutical compositions containing said compounds and to the novel intermediates used in the preparation of said compounds.
-
Paragraph 0090; 0091

(2013/06/27)

Amination of phenylketene revisit. Substituent effect on reactivity
The asymmetric stretching frequencies of the ketene group of the m,p-substituted phenylketenes were found to be correlated with σ The substituent effects for the second-order rate constants of phenylketenes with various amines were not correlated linearly
Badal, Md. Mizanur Rahman,Zhang, Min,Kobayashi, Shinjiro,Mishima, Masaaki
p. 856 - 863
(2013/08/15)

Structure-activity relationship for (+)-taxifolin isolated from silymarin as an inhibitor of amyloid β aggregation
Silymarin, the seed extract of Silybium marianum, has preventive effects against Alzheimer's disease-like pathogenesis in vivo. We isolated (+)-taxifolin (4) from silymarin as an inhibitor of aggregation of the 42- residue amyloid -protein. Structure-activity relationship studies revealed the 30,40-dihydroxyl groups to be critical to the anti-aggregative ability, whereas the 7-hydroxyl group and the stereochemistry at positions 2 and 3 were not important.
Sato, Mizuho,Murakami, Kazuma,Uno, Mayumi,Ikubo, Haruko,Nakagawa, Yu,Katayama, Sumie,Akagi, Ken-Ichi,Irie, Kazuhiro
p. 1100 - 1103
(2013/07/27)

METHODS OF TREATMENT USING ARYLCYCLOPROPYLAMINE COMPOUNDS
Described herein are methods of treating Parkinson's disease using arylcyclopropylamine compounds.
-
Paragraph 0236

(2013/07/19)