- Carbonylation of o-phenylenediamine and o-aminophenol with dimethyl carbonate using lead compounds as catalysts
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Lead compounds are active catalysts for carbonylation and carbonylation/methylation of o-phenylenediamine and o-aminophenol with dimethyl carbonate (DMC). 2-Benzimidazolone was obtained in 84% yield by the reaction of o-phenylenediamine with DMC for 1 h at 443 K in the presence of Pb(NO3)2. In the presence of Pb(OAc)2, the reaction quantitatively gave 1,3-dimethyl-2-benzimidazolone, which was formed by methylation of the primary product, 2-benzimidazolone, at 473 K. The effects of reaction variables on the yields of 2-benzimidazolone and 1,3-dimethyl-2-benzimidazolone were examined. The reaction of o-aminophenol with DMC selectively gave a carbonylation product, 2-benzoxazolone, or a carbonylation/methylation product, 3-methyl-2-benzoxazolone, depending on the reaction conditions in the presence of Pb(OAc)2.
- Fu, Yue,Baba, Toshihide,Ono, Yoshio
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- Discovery of a Highly Selective Sigma-2 Receptor Ligand, 1-(4-(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-3-methyl-1H-benzo[d]imidazol-2(3H)-one (CM398), with Drug-Like Properties and Antinociceptive Effects In Vivo
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The sigma-2 receptor has been cloned and identified as Tmem97, which is a transmembrane protein involved in intracellular Ca2+ regulation and cholesterol homeostasis. Since its discovery, the sigma-2 receptor has been an extremely controversial target, and many efforts have been made to elucidate the functional role of this receptor during physiological and pathological conditions. Recently, this receptor has been proposed as a potential target to treat neuropathic pain due to the ability of sigma-2 receptor agonists to relieve mechanical hyperalgesia in mice model of chronic pain. In the present work, we developed a highly selective sigma-2 receptor ligand (sigma-1/sigma-2 selectivity ratio > 1000), 1-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-3-methyl-1H- benzo[d]imidazol-2(3H)-one (CM398), with an encouraging in vitro and in vivo pharmacological profile in rodents. In particular, radioligand binding studies demonstrated that CM398 had preferential affinity for sigma-2 receptor compared with sigma-1 receptor and at least four other neurotransmitter receptors sites, including the norepinephrine transporter. Following oral administration, CM398 showed rapid absorption and peak plasma concentration (Cmax) occurred within 10?min of dosing. Moreover, the compound showed adequate, absolute oral bioavailability of 29.0%. Finally, CM398 showed promising anti-inflammatory analgesic effects in the formalin model of inflammatory pain in mice. The results collected in this study provide more evidence that selective sigma-2 receptor ligands can be useful tools in the development of novel pain therapeutics and altogether, these data suggest that CM398 is a suitable lead candidate for further evaluation.
- Avery, Bonnie A.,Chin, Frederick T.,Intagliata, Sebastiano,King, Tamara I.,Matsumoto, Rae R.,McCurdy, Christopher R.,McLaughlin, Jay P.,Mesangeau, Christophe,Seminerio, Michael,Sharma, Abhisheak,Wilson, Lisa L.
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- Study of unsaturated azoles. 16 Synthesis and reactions of 2-styrylbenzimidazoles
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Fusion of 1-methyl-2-styrylbenzimidazole with KOH leads to separation of the phenylvinyl or the N-methyl group to give 1-methylbenzimidazol-2-one or 2-styrylbenzimidazole in the ratio 1:1. Decomposition of the perbromides of benzimidazoles by heating in water gives 5(6)-bromobenzimidazoles and, in the presence of KI, to 5(6)-iodobenzimidazoles. Methods are presented for the synthesis of 5(6)-bromo- and 5(6)-iodo-2-styryl- and also 2-α-bromo- and 2-α-iodostyrylbenzimidazoles. 1998 Plenum Publishing Corporation.
- Popov
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- Direct Synthesis of N-Monosubstituted Benzimidazol-2-ones via Ph 3P-I 2-Mediated Reaction of Hydroxamic Acids
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A facile approach for the synthesis of benzimidazolones via a Ph3P-I2 promoted reaction of hydroxamic acids is reported. Upon Lossen-type rearrangement of the O-activated hydroxamic acids, the in situ generated isocyanates undergo an intramolecular attack by ortho N-nucleophiles producing the cyclized products in good yields under mild conditions. The method allows the direct preparation of a single regioisomer of N-monosubstituted derivatives using readily accessible starting materials and low-cost reagents with broad substrate scope.
- Hongsibsong, Surat,Pattarawarapan, Mookda,Phakhodee, Wong,Wiriya, Nittaya,Yamano, Dolnapa
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- Iron-Catalyzed Intramolecular C—H Amidation of N-Benzoyloxyureas
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A redox-neutral Fe-catalyzed intramolecular C—H amidation of N-benzoyloxyureas is described. This methodology employs a simple iron complex in situ generated from Fe(OTf)2 and bipyridine as the catalyst and N-benzoyloxyureas as the nitrene prec
- Zhong, Dayou,Wu, Lin-Yang,Wang, Xing-Zhen,Liu, Wen-Bo
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p. 855 - 858
(2021/02/16)
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- Efficient Amination of Activated and Non-Activated C(sp3)?H Bonds with a Simple Iron–Phenanthroline Catalyst
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A readily available catalyst consisting of iron dichloride in combination with 1,10-phenanthroline catalyzes the ring-closing C?H amination of N-benzoyloxyurea to form imidazolidin-2-ones in high yields. The C?H amination reaction is very general and applicable to benzylic, allylic, propargylic, and completely non-activated aliphatic C(sp3)?H bonds, and it also works for C(sp2)?H bonds. The surprisingly simple method can be performed under open flask conditions.
- Jarrige, Lucie,Zhou, Zijun,Hemming, Marcel,Meggers, Eric
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supporting information
p. 6314 - 6319
(2021/02/01)
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- Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone
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The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.
- Ando, Kaori,Oguchi, Mai,Kobayashi, Takahisa,Asano, Haruka,Uchida, Nariaki
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p. 9936 - 9943
(2020/09/04)
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- Photocatalytic Intramolecular C-H Amination Using N-Oxyureas as Nitrene Precursors
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Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.
- Ivanovich, Ryan A.,Polat, Dilan E.,Beauchemin, André M.
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supporting information
p. 6360 - 6364
(2020/09/02)
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- An Improved Synthesis of Urea Derivatives from N -Acylbenzotriazole via Curtius Rearrangement
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The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N -acyl, and cyclic ureas in good yields from N -acylbenzotriazoles by treating the latter with various amines in the presence of TMSN 3 /Et 3 N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.
- Agrahari, Anand K.,Singh, Anoop S.,Singh, Sumit K.,Tiwari, Vinod K.,Yadav, Mangal S.
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p. 3443 - 3450
(2019/09/07)
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- Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source
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A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.
- Qi, Xinxin,Zhou, Rong,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
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supporting information
p. 5161 - 5164
(2019/01/25)
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- Metal-free C(sp2)-H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination
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The direct C2-H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2-H oxidation, imination, and amination of azoles. Significantly, these reactions proceed under mild conditions with high to excellent yields, are scalable to large quantity and exhibit a broad substrate scope. Interestingly, this direct C2-H imination method allowed us to access various pharmacologically active N6-alkyl or N6-aryl substituted benzimidazoquinazolinone scaffolds through intramolecular C-H imination in a sequential one-pot reaction.
- Das, Ranajit,Banerjee, Mainak,Rai, Rakesh Kumar,Karri, Ramesh,Roy, Gouriprasanna
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p. 4243 - 4260
(2018/06/22)
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- Process Development of a CRF1 Receptor Antagonist Based on the Selective Chlorination of a Benzimidazolone via Chlorine Migration
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A practical synthesis of 4-chloro-2-(2,4-dichloro-6-methylphenoxy)-1-methyl-7-(pentan-3-yl)-1H-benzo[d]imidazole 1, a novel corticotropin-releasing factor 1 (CRF1) receptor antagonist, has been developed. The key chemical transformations were (1) a novel regioselective chlorination at the 4-position of a benzimidazolone intermediate with 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione in the presence of sodium tertiary butoxide via a chlorine migration mechanism (N-3 to C-4) and (2) a one-pot, three-step dehydroxylation sequence (dehydration, isomerization, and hydrogenation) of a benzylic tertiary alcohol in the presence of p-toluenesulfonic acid and a Pd catalyst. The endgame was also optimized for quality and yield improvement. The chromatography-free six-step process starting from a commercially available material afforded 1 in 35% overall yield and greater than 99% purity.
- Sawai, Yasuhiro,Yabe, Osamu,Nakaoka, Keiichiro,Ikemoto, Tomomi
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p. 222 - 230
(2017/02/26)
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- Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones
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There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.
- Sun, Chu-Han,Lu, Yi,Zhang, Qing,Lu, Rong,Bao, Lin-Qing,Shen, Mei-Hua,Xu, Hua-Dong
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supporting information
p. 4058 - 4063
(2017/07/10)
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- Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents
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A new Julia-type methylenation reagent, 1-methyl-2-(methylsulfonyl)benzimidazole (1e), reacts with a variety of aldehydes and ketones in the presence of either NaHMDS (-55 °C to rt) or t-BuOK (rt, 1 h) in DMF to give the corresponding terminal alkenes in high yields. The byproducts are easily removed, and the reaction conditions are mild and practical.
- Ando, Kaori,Kobayashi, Takahisa,Uchida, Nariaki
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supporting information
p. 2554 - 2557
(2015/05/27)
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- Highly stereoselective formal synthesis of rosuvastatin and pitavastatin through Julia-Kocienski olefination using the lactonized statin side-chain precursor
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An expedient and simple synthetic approach to pitava statin and rosuvastatin final intermediates is described. The presented approach consists of completely stereoselective Julia-Kocienski olefination step (E/Z up to 300:1) between lactonized statin side-chain precursor and sulfone derivative of the corresponding pyrimidine and quinoline heterocyclic cores. The desired O-TBS protected statin lactones were isolated in 66-71% yield and high >97% purity (HPLC). Georg Thieme Verlag Stuttgart. New York.
- Fabris, Jan,?asar, Zdenko,Smilovi?, Ivana Gazi?,?rnugelj, Martin
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p. 2333 - 2346
(2014/12/09)
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- Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs
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A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.
- Nakao, Syuhei,Mabuchi, Miyuki,Shimizu, Tadashi,Itoh, Yoshihiro,Takeuchi, Yuko,Ueda, Masahiro,Mizuno, Hiroaki,Shigi, Naoko,Ohshio, Ikumi,Jinguji, Kentaro,Ueda, Yuko,Yamamoto, Masatatsu,Furukawa, Tatsuhiko,Aoki, Shunji,Tsujikawa, Kazutake,Tanaka, Akito
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supporting information
p. 1071 - 1074
(2014/03/21)
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- DBU-based ionic-liquid-catalyzed carbonylation of o-phenylenediamines with CO2 to 2-benzimidazolones under solvent-free conditions
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Herein, a new route was presented to synthesize 2-benzimidazolones via the carbonylation of o-phenylenediamines with CO2 catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-based ionic liquids under solvent-free conditions. DBU acetate ([DBUH][OAc]) displayed high efficiency for catalyzing the reactions of CO2 with o-phenylenediamines, and a series of benzimidazolones were obtained in high yields. It was demonstrated that [DBUH][OAc] could serve as a bifunctional catalyst for these reactions with the cation activating CO2 and the anion activating o-phenylenediamines. This protocol provides an effective and environmentally friendly alternative route for production of benzimidazolones, and extends the chemical utilization of CO2 in organic synthesis as well.
- Yu, Bo,Zhang, Hongye,Zhao, Yanfei,Chen, Sha,Xu, Jilei,Hao, Leiduan,Liu, Zhimin
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p. 2076 - 2082
(2013/09/24)
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- CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS
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There are described cydohexyl amide derivatives useful as corticotropin releasing factor (CRF) receptor antagonists
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Page/Page column 92-93
(2016/02/02)
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- GSK-3BETA INHIBITOR
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For the purpose of providing a GSK-3β inhibitor containing a 2-aminopyridine compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (IA): wherein each symbol is as defined in the specification. or a salt thereof or a prodrug thereof.
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Page/Page column 32
(2011/04/13)
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- Synthesis of benzo-fused five- and six-membered heterocycles by palladium-catalyzed cyclocarbonylation
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A novel and simple synthetic methodology, based on palladium-catalyzed cyclocarbonylation reaction, is presented for preparing five- and six-membered benzo-fused heterocycles. A mechanism for the process is also proposed and discussed.
- Troisi, Luigino,Granito, Catia,Perrone, Serena,Rosato, Francesca
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experimental part
p. 4330 - 4332
(2011/09/13)
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- 1- Or 3-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2- ones: Potent, selective, and orally efficacious norepinephrine reuptake inhibitors
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Sequential structural modifications of the aryloxypropanamine template (e.g., atomoxetine, 2) led to a novel series of 1-(3-amino-2-hydroxy-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors (NRIs). In general, this series of compounds potently blocked the human norepinephrine transporter (hNET) while exhibiting selectivity at hNET against both the human serotonin (hSERT) and dopamine transporters (hDAT). Numerous compounds (e.g., 19-22) had low nonamolar hNET potency with IC 50 values of 7-10 nM and excellent selectivity (>500 fold) at hNET over hSERT and hDAT. Several compounds, such as 20 and 22, were tested in a telemetric rat model of ovariectomized-induced thermoregulatory dysfunction and were efficacious at oral doses of 3 mg/kg in reducing the tail skin temperature. In addition, compound 20 was also studied in the rat hot plate and spinal nerve ligation (SNL) models of acute and neuropathic pain, respectively, and was orally efficacious at doses of 3-10 mg/kg.
- Zhang, Puwen,Terefenko, Eugene A.,Bray, Jenifer,Deecher, Darlene,Fensome, Andrew,Harrison, Jim,Kim, Callain,Koury, Elizabeth,Mark, Lilly,McComas, Casey C.,Mugford, Cheryl A.,Trybulski, Eugene J.,Vu, An T.,Whiteside, Garth T.,Mahaney, Paige E.
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experimental part
p. 5703 - 5711
(2010/02/28)
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- Synthesis and activity of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors
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A series of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors was discovered. Several compounds such as 15 and 20 showed good hNET potency. Compounds 15 and 20 also displayed excellent selectivity at hNET that appeared superior to those of reboxetine and atomoxetine (4 and 5).
- Zhang, Puwen,Terefenko, Eugene A.,McComas, Casey C.,Mahaney, Paige E.,Vu, An,Trybulski, Eugene,Koury, Elizabeth,Johnston, Grace,Bray, Jenifer,Deecher, Darlene
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scheme or table
p. 6067 - 6070
(2009/08/07)
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- Benzimidazolones and indoles as non-thiol farnesyltransferase inhibitors based on tipifarnib scaffold: Synthesis and activity
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A series of analogs of tipifarnib (1) has been synthesized as inhibitors of FTase by substituting the benzimidazolones and indoles for the 2-quinolone of tipifarnib. The novel benzimidazolones are potent and selective FTase inhibitors (FTIs) with IC50 values of the best compounds close to that of tipifarnib. The current series demonstrate good cellular activity as measured in their inhibiting the Ras processing in NIH-3T3 cells, with compounds 2c and 2f displaying EC50 values of 18 and 22 nM, respectively.
- Li, Qun,Li, Tongmei,Woods, Keith W.,Gu, Wen-Zhen,Cohen, Jerry,Stoll, Vincent S.,Galicia, Tomas,Hutchins, Charles,Frost, David,Rosenberg, Saul H.,Sham, Hing L.
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p. 2918 - 2922
(2007/10/03)
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- Selenium-catalyzed reductive carbonylation of 2-nitrophenols to 2-benzoxazolones
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2-Benzoxazolones or 2-benzimidazolones are synthesized in moderate to good yields in the presence of a base (KOH, NaOH, KOAc, NEt3, DBU) at atmospheric pressure or under a high pressure of CO by one-pot reductive carbonylation of 2-nitrophenols or 2-nitroaniline in the presence of selenium as catalyst. Besides the effect of base, the effects of solvent and temperature on the reaction were investigated at high or atmospheric pressure. Contrasting results were obtained for 2-benzoxazolones or 2-benzimidazolone at high and atmospheric pressures. Moreover, phase-transfer catalysis was exhibited. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Wang, Xiaofang,Ling, Gang,Xue, Yan,Lu, Shiwei
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p. 1675 - 1679
(2007/10/03)
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- Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides
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2-Amino-, and 2-alkyl-benzothiazoles have been efficiently prepared by palladium catalyzed cyclization of o-bromophenylthioureas and o-bromophenylthiamides. Results were best with the Pd2(dba)3/monophosphine catalytic system.
- Benedí, Carolina,Bravo, Fernando,Uriz, Pedro,Fernández, Elena,Claver, Carmen,Castillón, Sergio
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p. 6073 - 6077
(2007/10/03)
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- Benzimidazolone derivatives displaying affinity at the serotonin and dopamine receptors
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Compound of formula (I) wherein: R1 is hydrogen or C1-C6-alkyl optionally substituted by C3-C6-cycloylalkyl; R2 and R3 together with the nitrogen form a saturated or unsaturated 5- or 6-membered heterocyclic ring optionally containing nitrogen or oxygen as an additional heteroatom, wherein the heterocyclic ring thereof is substituted by a group selected from phenyl, benzyl, and diphenylmethyl, each optionally mono- or di-substituted by one or two groups selected from CF3, C1-C4-alkyl, C1-C4-alkoxy, phenyl, benzyl, halogen, and OH, or R2 and R3 together with the nitrogen form a saturated or unsaturated 5- or 6-membered heterocyclic ring optionally containing nitrogen or oxygen as an additional heteroatom, the heterocyclic ring thereof linked via a single bond, a methylene-bridge, or spiro-connected to another saturated or unsaturated heterocyclic group containing one or two heteroatoms selected from oxygen and nitrogen, the heterocyclic group being optionally mono- or di-substituted by a group selected from CF3, C1-C4-alkyl, C1-C4-alkoxy, phenyl, benzyl, halogen, =O, and OH, or R2 and R3 together with the nitrogen form a saturated or unsaturated bi- or tricyclic heterocyclic ring system optionally containing nitrogen or oxygen as an additional heteroatom, the heterocyclic ring system is optionally substituted by a group selected from CF3, C1-C4-alkyl, C1-C4-alkoxy, phenyl, benzyl, halogen, =O, and OH; and A is C2-C6-alkenylene, their pharmaceutically acceptable salts, their preparation, and their use for therapeutic purposes.
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- Synthesis of a regio-isomer of kealiiquinone, a marine benzimidazole alkaloid
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Treatment of 1,3-dialkyl-2-(phenylthio)benzimidazolium salts 3 and 1,3-dialkyl-2-phenylthio-1H-imidazolium salts 7 with aq. K2CO3 gives 1,3-dialky1-1,3-dihydrobenzimidazol-2-ones 4 and 1,3-dialkyl-1,3-dihydroimidazol-2-ones 8, respectively, in 22-94% yield. A regio-isomer 17 of kealiiquinone, a marine benzimidazole alkaloid, where the 4-methoxyphenyl group at the 4-position migrates to the 9-position, is synthesized by application of the reaction. Cytotoxity of 17 and kealiiquinone against 39 human cancer cells is evaluated. They have weak activity but a unique mechanism of action.
- Nakamura, Seikou,Tsuno, Naoki,Yamashita, Masayuki,Kawasaki, Ikuo,Ohta, Shunsaku,Ohishi, Yoshitaka
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p. 429 - 436
(2007/10/03)
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- Hypervalent iodine oxidative rearrangement of anthranilamides, salicylamides and some β-substituted amides: A new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds
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Oxidation of anthranilamides, salicylamides and some β-substituted amides with iodobenzene diacetate in methanolic potassium hydroxide led to a new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, respectively. The reaction probably occurs via initial Hofmann-type rearrangement followed by intramolecular cyclization of intermediate isocyanate.
- Prakash,Batra,Kaur,Sharma,Sharma,Singh,Moriarty
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p. 541 - 543
(2007/10/03)
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- Oxidative cyclization of acyclic ureas with bis(trifluoroacetoxy)iodobenzene to generate N-substituted 2-benzimidazolinones
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A facile method to synthesize N-substituted 2-benzimidazolinones from secondary aromatic amines is presented. Sequential treatment of a secondary aromatic amine with phosgene and methoxylamine afforded an acyclic 3-substituted 3-aryl-1-methoxy urea. Brief
- Romero, Arthur G.,Darlington, William H.,Jacobsen, E. Jon,Mickelson, John W.
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p. 2361 - 2364
(2007/10/03)
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- Highly effective procedure for introduction of amino group into the 2-position of imidazole ring
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Procedures for the preparation of 2-amino- and 2-arylaminobenzimidazoles were developed, and one of the efficient procedure was applied to the synthesis of preclathridine A, a marine imidazole alkaloid isolated from a sponge.
- Kawasaki, Ikuo,Taguchi, Norio,Yoneda, Youko,Yamashita, Masayuki,Ohta, Shunsaku
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p. 1375 - 1379
(2007/10/03)
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- Investigations of unsaturated azoles. 14. Reaction of benzimidazole and its derivatives with p-nitrostyrene oxide. Quaternary ammonium bases
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The reactions of benzimidazole and its 2- and 1-alkyl, 2-mercapto, and 2-amino derivatives with p-nitrostyrene oxide have been studied. 1997 Plenum Publishing Corporation.
- Popov,Konstantinchenko
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p. 1160 - 1165
(2007/10/03)
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- BENZIMIDAZOLINONES SUBSTITUTED WITH PHENOXYPHENYLACETIC ACID DERIVATIVES
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Phenoxyphenylacetic acids and derivatives of the general structural formula I STR1 have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.
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- A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM
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Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.
- Yoshida, Tohru,Kambe, Nobuaki,Ogawa, Akiya,Sonoda, Noboru
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p. 137 - 148
(2007/10/02)
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- Nucleophilic Substitution in Quaternary Salts of NN'-Linked Biazoles and Related Systems.
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Some reactions of dicationic and monocationic N,N'-linked biazoles and of quaternized 1-(N-azolyl)pyridinium ions with nucleophiles have been studied.Although the pyrrolyl nucleus has been found to be a poor leaving group in these reactions, in other cases nucleophilic attack readily takes place at an azolyl carbon atom, with subsequent elimination of the N-substituent.The 1-methyl-3-(1-methyl-1,2,4-triazol-4-ylio)benzimidazolium dication (1) reacted at room temperature with ammonium, diethylamine, methoxyde, hydroxide, and cyanide ions, and with sodium borohydride, giving in all cases the corresponding 2-substituted benzimidazoles in good yield.In the case of the 2,4,6-trimethyl-1-(2-methylpyrazol-1-io)pyridinium dication (6), the reaction with cyanide ion afforded, regioselectively, 5-cyano-1-methylpyrazole, with no trace of the isomeric 3-cyano-1-methylpyrazole.The synthesis of the cations and dications from N-aminoazoles was easily performed.The reaction of 1-aminobenzimidazole with dehydroacetic acid in aqueous hydrochloric acid gave not only the expected 1-benzimidazol-1-yl-2,6-dimethylpyridin-4(1H)-one (9), but also 3-acetyl-1-benzimidazol-1-yl-4-hydroxy-6-methylpyridin-2(1H)-one (11).In pyridine, a pyran-2,4-dione intermediate (10), isomeric to (11), was also isolated.The quaternization reactions were easily performed, but high temperatures caused cleavage of the N-N bond.
- Castellanos, Maria Luisa,Llinas, Montserrat,Bruix, Marta,Mendoza, Javier de,Martin, M. Rosario
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p. 1209 - 1216
(2007/10/02)
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- Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides
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Alkylation of 1-phenyltetrazolone 10a with 2-cyclohexen-1-yl bromide followed by dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone permits introduction of a phenyl group at N-4 of the tetrazole ring via the sequence 10a -> 10f -> 10g.The photoextrusion of molecular nitrogen from the (N-4)-substituted 1-phenyltetrazolones, 10a (hydrogen), 10b (methyl), 10d,e (propenyl), and 10g (phenyl) produces essentially quantitative yields of the corresponding benzimidazolones 14a,b,d,e,g.On irradiation of the 1-phenyltetrazolethiones 8b,f,g the carbodiimides 22b,f,g are obtained together with molecular nitrogen and sulfur, while 8a affords phenylcyanamide (25).In contrast to the thermolysis, which is known to give 2-(methylamino)benzothiazole (21b), photolysis of the (phenylimino)-1,2,3,4-thiatriazole 24, an isomer of methylphenyltetrazolethione 8b, also yields molecular nitrogen, sulfur, and methylphenylcarbodiimide (22b).
- Quast, Helmut,Nahr, Uwe
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p. 526 - 540
(2007/10/02)
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- Facile Synthesis of Benzimidazol-2-one Derivatives by Modified Lossen Rearrangement
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A "formamide modification" has been applied to the Lossen rearrangement of several biologically important anthranilohydroxamic acids, some of them prepared for the first time.It has been found that a short heating at temperatures in the range 130-140 deg C converts these compounds into corresponding benzimidazol-2-ones with excellent yields.
- Eckstein, Zygmunt,Jadach, Tadeusz,Lipczynska-Kochany, Ewa
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p. 279 - 281
(2007/10/02)
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- Synthesis of 1-Alkyl and 1,3-Dialkyl-2-benzimidazolones from 1-Alkenyl-2-benzimidazolones using Phase-Transfer Catalysts Technique
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A general synthetic route to 1-alkyl and 1,3-dialkyl-2-benzimidazolones from 1-alkenyl-2-benzimidazolenes using phase-transfer catalysis conditions is described.
- Vernin, Gaston,Domlog, Hicham,Siv, Chan,Metzger, Jaques,El-Shafei, Ahmed Kamal
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- STEREOSELECTIVE SYNTHESIS OF D- AND L-RIBOSE
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The allylcadmiun compound, prepared in situ from 2-allyl-oxybenzimidazole, reacts with 2,4-O-isopropylidene-D and L-glyceraldehyde in highly regio- and stereoselective manner to give the corresponding enantiomeric adducts.The adducts are further transform
- Yamaguchi, Masahiko,Mukaiyama, Teruaki
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p. 1005 - 1008
(2007/10/02)
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- 7-[α-(2,3-DIHYDRO-2-OXO-1H-benzimidazol-1-ylcarbonyl-amino)arylacetamido]cephalosporins
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Cephalosporin antibiotics of the formula STR1 in which, for example, R is phenyl, hydroxyphenyl, halophenyl, thienyl, or furyl; R1 is hydrogen, carbamoyloxy, acetoxy, a lower alkyl substituted 1H-tetrazol-5-ylthio or 1,3,4-thiadiazol-5-ylthio group; and R2 is hydrogen or methyl; are highly active broad spectrum antibiotics especially useful in the treatment of infections attributable to the gram-negative microorganisms.
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- New investigations on the chemical behavior of 4-keto-1H-4,5-dihydro-1,2,5-benzotriazepines
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The chemical behavior of 4-keto-1H-4,5-dihydro-1,2,5-benzotriazepines towards basic reagents has been investigated. Evidence is given that 4-keto-1H-4,5-dihydro-1,2,5-benzotriazepines unsubstituted at position 3 are cleaved by sodium hydroxide and alkoxides furnishing sodium cyanide and 2-amino-3-keto-quinoxalines. The same benzotriazepines substituted by a carbamidoximo- or a carbohydrazino-group at position 3 undergo, when treated with the same reagents, isomerization reactions yielding 3-amino-4-arylazo-isoxazolin-5-ones and 4-arylazo-pyrazolidin-3,5-diones respectively. The structure of these products is demonstrated and a mechanism for their formation is proposed.
- Bianchi,Butti,Rossi
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p. 2765 - 2771
(2007/10/08)
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