202865-66-5Relevant articles and documents
Benzoxaborole-1-alcohol compound and preparation method and application thereof
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Paragraph 0078-0084, (2020/06/24)
The invention belongs to the field of bactericides, and particularly relates to a benzoxaborole-1-alcohol compound and a preparation method and application thereof. The benzoxaborole-1-alcohol compound has good bactericidal activity, can effectively control tomato early blight, wheat scab, rice sheath blight disease, strawberry gray mold, apple blotch, cucumber anthracnose and other crop diseases,can produce excellent antibacterial effects at low concentration, and shows good selectivity. The compound is used as a leucyl-tRNA synthetase inhibitor, the evolution difference of aminoacyl-tRNA synthetase of germs and eukaryotes is utilized, and the compound has very high safety to non-target organisms while killing the germs and can be used as a bactericide in agriculture.
Design, synthesis and biological evaluation of 6-deoxy O-spiroketal C-arylglucosides as novel renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes
Wang, Yibing,Lou, Yang,Wang, Jiang,Li, Dan,Chen, Hui,Zheng, Tiannan,Xia, Chunmei,Song, Xiaohan,Dong, Tiancheng,Li, Jingya,Li, Jia,Liu, Hong
, p. 398 - 416 (2019/07/19)
In this work, aiming at finding a novel, potent, and selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor with good pharmacokinetic profiles for the treatment of diabetes, we focus on modifying the sugar moiety of SGLT2 inhibitors, which dominates the binding with glucose binding site of hSGLT, via removing the C-6 hydroxy group to adjust the physicochemical properties and target-recognition manners of SGLT2 inhibitors. In addition, tofogliflozin containing a special O-spiroketal C-arylglucoside scaffold, displayed good efficacy and bioavailability both in animals and in humans. Therefore, a series of 6-deoxy O-spiroketal C-arylglucosides as novel SGLT2 inhibitors were designed, synthesized, and evaluated in this work. The structure-activity relationship (SAR) research on this novel series and a comprehensive in vitro and in vivo biological evaluation afforded compound 39 with high in vitro hSGLT2 inhibitory activity (IC50 = 4.5 nM), good pharmacokinetic profiles, and more remarkable efficacy in C57BL/6J mice and Sprague-Dawley rats than marketed drug tofogliflozin.
Metal- and Hydride-Free Pentannulative Reductive Aldol Reaction
Satpathi, Bishnupada,Dutta, Lona,Ramasastry
supporting information, p. 170 - 174 (2019/01/04)
Traditionally, the reductive aldol reaction is a metal-catalyzed and hydride-promoted coupling between enones and aldehydes. We present a phosphine-mediated diastereoselective intramolecular reductive aldol reaction of α-substituted dienones and aldehydes, which is metal-free and hydride-free. The synthetic utility of the reductive aldol adducts is demonstrated by elaborating them in one step to indeno[1,2-b]furanones, indeno[1,2-b]pyrans, and dibenzo[a,h]azulen-8-ones.
Copper-Catalyzed Aerobic Oxidative Cyclization Cascade to Construct Bridged Skeletons: Total Synthesis of (?)-Suaveoline
Tan, Qiuyuan,Yang, Zhao,Jiang, Dan,Cheng, Yuegang,Yang, Jiao,Xi, Song,Zhang, Min
supporting information, p. 6420 - 6424 (2019/04/13)
Based on the discovery of copper-catalyzed cyclopropanol ring-opening addition to iminium ions, an unprecedented catalytic aerobic C?H oxidation/cyclopropanol cyclization cascade using CuCl2 as the multifunctional catalyst and air as the oxidant was developed to construct the azabicyclo[3.3.1]nonane skeleton, which is widespread in natural products and medicines. Using this method, concise asymmetric total synthesis of the indole alkaloid (?)-suaveoline was achieved. This study not only provides an efficient, low-cost, and environmentally benign method for constructing such bridged frameworks, but also enriches the realm of cyclopropanol chemistry and C?H functionalization.
Indolone derivative as well as preparation method and application thereof
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Paragraph 0268-0269, (2019/07/04)
The invention relates to a compound represented by formula (A) or a pharmaceutically acceptable salt, a stereoisomer, a tautomer, a polymorphic substance, a solvate, a metabolite or a prodrug thereof,and also relates to a pharmaceutical composition containing the compound. The compound can be used for treating cancer or immune system diseases.
Preparation method of easy-to-purify benzoxaborole antifungal drug
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Paragraph 0016; 0057; 0058-0060; 0062; 0069; 0071; 0078, (2018/09/08)
The invention discloses a preparation method of an easy-to-purify benzoxaborole antifungal drug, which comprises the following steps: (1) a compound I is reduced by sodium borohydride, so that a compound II is obtained; (2) under an alkaline condition, a compound III is obtained from the compound II with DMAP as a catalyst under the protection of triphenylchloromethane; (3) the compound III undergoes bromine-lithium exchange reaction; after triisopropyl borate is added for reaction, hydrolysis is carried out, so that an intermediate is obtained, and the intermediate undergoes deprotection andring closure, and the benzoxaborole antifungal drug shown as a compound IV is obtained. Because the preparation method replaces chloromethyl methyl ether used for hydroxy group protection in the conventional 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole synthesis route with triphenylchloromethane, a solid protecting group is formed, refinement and purification are easy, the purification processis simplified, the purity of the product is increased, and the production cost is also reduced.
Based on 4 - phenyl -6 - (2, 2, 2 - trifluoro -1 - phenyl ethoxy) pyrimidine compound and its application method
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Paragraph 0270, (2017/08/25)
The present invention relates to compounds based on 4-phenyl-6-(2,2,2-trifluoro-1-phenyl ethoxy) pyrimidine and an application method thereof, particularly discloses compounds of formula I and compositions comprising the compounds, and the application method thereof in treatment, prevention and / or management of diseases or disorders.
An enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (IMBH) reaction of dienones, and elaboration of the IMBH adducts to fluorenones
Satpathi, Bishnupada,Wagulde, Siddhant V.,Ramasastry
supporting information, p. 8042 - 8045 (2017/07/22)
An enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (IMBH) reaction of dienones is reported for the first time. This has been achieved by incorporating entropy and synergy considerations during the substrate design. The reaction conditions are thoroughly verified for an efficient synthesis of highly functionalised cyclopenta-fused arenes and heteroarenes in excellent yields and enantioselectivities. The synthetic utility of the IMBH-adducts has been demonstrated by transforming them into 3,4-disubstituted fluorenones in a serendipitous manner.
Morita-Baylis-Hillman Reaction of β,β-Disubstituted Enones: An Enantioselective Organocatalytic Approach for the Synthesis of Cyclopenta[b]annulated Arenes and Heteroarenes
Satpathi, Bishnupada,Ramasastry
supporting information, p. 1777 - 1781 (2016/02/03)
The first enantioselective organocatalytic intramolecular Morita-Baylis-Hillman (MBH) reaction of sterically highly demanding β,β-disubstituted enones is presented. The MBH reaction of β,β-disubstituted-α,β-unsaturated electron-withdrawing systems was previously considered to be unfeasible. Towards this end, designer substrates, which under simple and practical reaction conditions generate a variety of cyclopenta[b]annulated arenes and heteroarenes in excellent enantiopurities and near-quantitative yields in remarkably short reaction times, are described. The reason for the unusually facile nature of this reaction is attributed to the synergy guided and entropically favored intramolecular reaction. Further, this strategy provides easy access to a substantial number of bioactive natural products and pharmaceutically significant compounds.
Selective acetylation of primary alcohols by ethyl acetate
Singha, Raju,Ray, Jayanta K.
supporting information, p. 5395 - 5398 (2016/11/11)
A KOtBu and ethyl acetate mediated efficient methodology has been developed for the acetylation of primary and secondary alcohols where ethyl acetate is the source of acetyl group. The reaction is fast, mild, efficient, and highly selective towards the primary alcohols.