- Design, synthesis and antioxidant activity of chalcone derivative CMZ-3-5
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Excessive accumulation of free radicals can cause a variety of diseases. According to reports, chalcone has the activity of scavenging free radicals. In this study, we synthesized a chalcone derivative CZM-3-5 and evaluated its antioxidant activity using
- Gao, Feng,Kong, Xiangshun,Liu, Jiang,Teng, Yuou,Xiang, Cen,Yuan, Yuan,Zhao, Yufan
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p. 598 - 605
(2021/12/04)
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- One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis
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A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(iii) triflimide catalysed iodination, followed by a copper(i)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.
- Henry, Martyn C.,McGrory, Rochelle,Faggyas, Réka J.,Mostafa, Mohamed A. B.,Sutherland, Andrew
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p. 4629 - 4639
(2019/05/17)
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- An Improved Synthesis of Elvitegravir
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An improved process for the active pharmaceutical ingredient of a new HIV integrase inhibitor elvitegravir (1) has been developed. It starts from commercially available 2,4-dimethoxyacetophenone, which is selectively halogenated into the position 5. The 5-halo acetophenones are condensed with dialkyl carbonates to give the corresponding benzoylacetates. Their treatment with N,N-dimethylformamide dimethyl acetal followed by (S)-valinol then provided the corresponding intermediate benzoyl acrylates. Cyclization to the required 1,4-dihydroquinolin-4-oxo derivatives by aromatic nucleophilic substitution of the 2-methoxy group was achieved by treatment with N,O-bis(trimethylsilyl)-acetamide, which also protected the OH group as the trimethylsilyl derivative. Finally, the Negishi coupling with 2-fluoro-3-chlorobenzylzinc bromide and the following hydrolysis provided elvitegravir (1). The preferred variant, the seven-step procedure starting from 2,4-dimethoxyacetophenone, provides elvitegravir in 29.3% yield.
- Rádl, Stanislav,Stach, Jan,Pí?a, Ond?ej,Cinibulk, Josef,Havlí?ek, Jaroslav,Zajícová, Markéta,Pekárek, Tomá?
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p. 1738 - 1749
(2016/11/23)
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- A NEW PRODUCTION METHOD AND NEW INTERMEDIATES OF SYNTHESIS OF ELVITEGRAVIR
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The present solution relates to an improved production method of elvitegravir of formula I, which is being clinically evaluated for treatment of HIV infection. Elvitegravir of formula I is produced via the intermediate of formula II, the preparation of which is also an object of the present solution.
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Page/Page column 13
(2014/05/07)
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- Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system
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The novel reaction system comprising air/NH4NO3(cat.)/I2/H2SO4(cat.)is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative α-iodination of aryl, heteroaryl, alkyl, and cycloalkyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved.
- Prebil, Rok,Stavber, Stojan
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supporting information
p. 5643 - 5647
(2014/12/11)
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- Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
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The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
- Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
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- A new method for halogenation of aromatic compounds by using dimethyldioxirane and tetrabutylammonium halides
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In this presentation the novel regioselective halogenation of arenes or phenols with dimethyldioxirane and Bu4NX is described. The results showed that a new, versatile and mild method can be utilized for preparation of aryl halides starting with arenes or phenols. Finally, this aryl halide forming methodology is applicable to structurally more complex flavonoids.
- Lee, Yean-Jang,Wu, Huan-Ting,Lin, Chia-Ning
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experimental part
p. 585 - 587
(2010/04/23)
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- 1,5-DIPHENYLPYRAZOLES II AS HSP90 INHIBITORS
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Novel 1,5-diphenylpyrazole derivatives of the formula (I) in which R1-R6 have the meanings indicated in claim 1, are HSP90 inhibitors and can be used for the preparation of a medicament for the treatment of diseases in which the inhi
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Page/Page column 16
(2010/01/31)
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- 1,5-Diphenylpyrazole
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The invention relates to novel 1,5-diphenylpyrazole derivatives of formula (I), where R1-R6 have the meanings given in claim 1, which are HSP90 inhibitors and which can be used for the production of a medicament for the treatment of diseases in which the inhibition, regulation and/or modulation of HSP90 plays a role
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Page/Page column 83
(2010/10/20)
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- Solvent directed electrophilic iodination and phenylselenenylation of activated alkyl aryl ketones
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A mixture of molecular iodine and phenyliodine(III) bis(trifluoroacetate) (BTI) in CH3CN (or CH3OH) iodinates the aromatic ring of some activated alkyl aryl ketones. A different outcome results if PhSeSePh is used instead of I2
- Panunzi, Barbara,Rotiroti, Lucia,Tingoli, Marco
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p. 8753 - 8756
(2007/10/03)
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- Selectfluor F-TEDA-BF4 mediated and solvent directed iodination of aryl alkyl ketones using elemental iodine
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Reactions of aryl alkyl ketones with methanol solution of elemental iodine and 1-fluoro-4-chloromethyl-1,4-diazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF4) result in the formation of corresponding α-iodo ketones, wh
- Stavber, Stojan,Jereb, Marjan,Zupan, Marko
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p. 488 - 489
(2007/10/03)
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- Regioselective Synthesis of Prenylisoflavones. Syntheses of Lupiwighteone, Lupiwighteone Hydrate and Related Compounds
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The palladium-catalyzed coupling reaction of 4',5.7-tris(benzyloxy)-8-iodoisoflavone 11, synthesized from the 3'-iodochalcone 8, with 2-methyl-3-butyn-2-ol gave the corresponding 8-(3-hydroxy-3-methylbutynyl)isoflavone 12.Catalytic hydrogenation of 12 gav
- Tsukayama, Masao,Li, He,Nishiuchi, Masaki,Takahashi, Masahumi,Kawamura, Yasuhiko
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p. 1181 - 1196
(2007/10/03)
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- REGIOSELECTIVE PRENYLATION OF PHENOLS BY PALLADIUM CATALYST: SYNTHESES OF PRENYLPHENOLS AND CHROMANS
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The palladium-catalyzed coupling reaction of iodophenols (1) with 2-methyl-3-butyn-2-ol gave alkynylphenols (2).Catalytic hydrogenation of 2 over Raney nickel and the subsequent dehydration of the resultant alkylphenols (3) gave regioselectively the desired prenylphenols (4).Dehydration of alkylphenols (3f-h) gave chromans (7).
- Tsukayama, Masao,Kikuchi, Makoto,Kawamura, Yasuhiko
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p. 1487 - 1490
(2007/10/02)
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