- Selenium-catalyzed intramolecular atom- And redox-economical transformation ofo-nitrotoluenes into anthranilic acids
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Anthranilic acids (AAs) are significant basic chemicals used in pharmaceuticals, agrochemicals, dyes, fragrances,etc. Superfluous steps are always involved in obtaining AAs. Herein, we demonstrate a straightforward strategy to transform abundanto-nitrotoluenes into biologically and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines,etc., can be tolerated in this transformation. A hundred-gram-scale operation is realized efficiently with almost quantitative selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species.
- Jiang, Xuefeng,Li, Yiming,Lin, Zhenyang,Wang, Yuhong,Yang, Tilong
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supporting information
p. 2986 - 2991
(2021/05/05)
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- Anthranilic acid and derivatives thereof as well as synthesis method and application thereof
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In the reaction solvent, o-methyl (hetero) aryl nitro compound is taken as a reaction raw material and is used for water. The anthranilic acid and its derivatives are synthesized by the action of a catalyst, a base and an additive. The synthetic method has the advantages of cheap and easily available raw materials, simple reaction operation, high yield and excellent functional group tolerance, and provides a simple and efficient method for synthesizing o-aminobenzoic acid which is widely used in the aspects of dyes, medicines, pesticides, spices and the like. The invention further discloses the anthranilic acid and derivatives and application thereof, and has a wide application prospect.
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Paragraph 0128-0130
(2021/09/15)
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- Development of 2-arylbenzo[: H] quinolone analogs as selective CYP1B1 inhibitors
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The CYP1B1 enzyme is regarded as a potential target for cancer prevention and therapy. Based on the structure of α-naphthoflavone (ANF), diverse 2-arylbenzo[h]quinolone derivatives were designed, synthesized and evaluated as selective CYP1B1 inhibitors. Compared with ANF, although few of the title compounds possessed comparable or slightly higher CYP1B1 inhibitory activity, these compounds displayed a significantly increased selectivity toward CYP1B1 over CYP1A2. Among them compounds 5e, 5g and 5h potently inhibited the activity of CYP1B1 with IC50 values of 3.6, 3.9 and 4.1 nM respectively, paralleled by an excellent selectivity profile. On the basis of predicted clogP values, these target compounds may exhibit improved water-solubility compared to ANF. In particular, 5h showed a great superiority in the reversal of CYP1B1-mediated docetaxel resistance in vitro. The current study may serve as a good starting point for the further development of more potent as well as specific CYP1B1 inhibitors capable of reversing CYP1B1-mediated anticancer-drug resistance.
- Dong, Jinyun,Wang, Zengtao,Meng, Qingqing,Zhang, Qijing,Huang, Guang,Cui, Jiahua,Li, Shaoshun
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p. 15009 - 15020
(2018/04/30)
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- PROCESS FOR MAKING M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS
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This invention provides novel processes for the preparation of compounds such as 3-[(1S,2S)-2-hydroxycyclohexyl]-6-[(6-methylpyridin-3-yl)methyl]benzo[h]-quinazolin-4(3H)-one, salts and derivatives thereof. The compounds synthesized by the processes of the invention are useful for treating Alzheimer's disease and other diseases (e.g., cognitive impairment, schizophrenia, pain disorders, and sleep disorders) mediated by the muscarinic M1 receptor.
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- Methods and compositions for selectin inhibition
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The present invention relates to the field of anti-inflammatory substances, and more particularly to novel compounds that act as antagonists of the mammalian adhesion proteins known as selectins. In some embodiments, methods for treating selectin mediated disorders are provided which include administration of compound of Formula I: wherein the constituent variables are defined herein.
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Page/Page column 16
(2008/06/13)
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- Total synthesis of 3,4-dihydrobenzo[h]quinazolin-4-one and structure elucidation of perlolidine and samoquasine A
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The total synthesis of 3,4-dihydrobenzo[h]quinazolin-4-one is described. Based on the spectral data and chemical evidence, the structures of 3,4-dihydrobenzo[h]quinazolin-4-one, perlolidine, and samoquasine A are not the same. A structure for samoquasine A is suggested.
- Yang, Yu-Liang,Chang, Fang-Rong,Wu, Yang-Chang
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p. 319 - 322
(2007/10/03)
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- Synthesis of Benzo-Fused Benzodiazepines Employed as Probes of the Agonist Pharmacophore of Benzodiazepine Receptors
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The synthesis and in vitro evaluation of benzo-fused benzodiazepines 1-6 are described.These "molecular yardsticks" were employed to probe the spatial dimensions of the lipophilic pocket L2 in the benzodiazepine receptor (BzR) cleft and to dete
- Zhang, Weijiang,Koehler, Konrad F.,Harris, Bradford,Skolnick, Phil,Cook, James M.
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p. 745 - 757
(2007/10/02)
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- Iodosonaphthoate catalysts for the cleavage of a reactive phosphate
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Iodosonaphthoates 3-5 are potent catalysts for the hydrolysis of P-nitro-phenyldiphenyl phosphate.
- Moss, Robert A.,Zhang, Hongmei,Chatterjee, Swati,Krogh-Jespersen, Karsten
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p. 1729 - 1732
(2007/10/02)
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- The Regiospecific Synthesis Of Ortho Aminonaphthophenones Via The Addition Of Carbanions To Naphthoxazin-4-Ones
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The conversion of nitronaphthalenes (see 4a and 4b) into the corresponding ortho aminonaphthylnitriles (5a and 5b) via the process of Tomioka, when combined with the addition of carbanions to the intermediate naphthoxazin-4-ones, provided a route to ortho aminonaphthophenones (7a) and (7b).These key intermediates were employed to synthesize the benzfused 2'-fluoro-1,4-benzodiazepines (1-3).
- Zhang, Weijiang,Liu, Ruiyan,Cook, James M.
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p. 2229 - 2236
(2007/10/02)
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- Synthesis of New Heterocycles: Condensation of 2-Methyl-4H-naphthoxazin-4-one with Schiff Bases and Formation of 3-Aryl-2-styrylbenzoquinazolin-4(3H)-ones
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Condensation of 2-Methyl-4H-naphthoxazin-4-one (2) with Schiff bases (3) in acetic acid has resulted in 3-aryl-2-styrylbenzoquinazolin-4(3H)-ones (4), characterized by spectral and analytical methods.
- Reddy, Mandala Satyanarayana,Ratnam, Chengalvala Venkata
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p. 2449 - 2450
(2007/10/02)
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