35750-24-4Relevant academic research and scientific papers
Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes
Yu, Congjun,?zkaya, Bünyamin,Patureau, Frederic W.
supporting information, p. 3682 - 3687 (2021/02/01)
A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.
Elastase Inhibitor Cyclotheonellazole A: Total Synthesis and in Vivo Biological Evaluation for Acute Lung Injury
Chen, Yue,Cui, Yingjun,Deng, Yangping,Fu, Qiang,Jiang, Peng,Li, Jing,Lin, Jianping,Liu, Yang,Meng, Qing,Sun, Yuanjun,Wang, Liang,Wang, Mukuo,Xu, Honglei,Ye, Baijun,Zhang, Mengyi,Zhang, Songming,Zhang, Tingrong,Zhao, Xiuhe
, (2022/01/27)
Acute lung injury/acute respiratory distress syndrome (ALI/ARDS) is one of the most common complications in COVID-19. Elastase has been recognized as an important target to prevent ALI/ARDS in the patient of COVID-19. Cyclotheonellazole A (CTL-A) is a nat
DEUTERIUM-ENRICHED SUBSTITUTED PHENOXYPHENYL ACETIC ACIDS AND ACYLSULFONAMIDES
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Page/Page column 23; 32, (2021/06/22)
The present invention is concerned with deuterium-enriched substituted phenoxy-(3, 4-methylenedioxy)phenylacetic acid and acylsulfonamide derivatives of general structural formula I, their optically active or pure enantiomers and diastereomers, and pharmaceutical salts thereof, Formula (I) These compounds have selective antagonist activity for endothelin receptors or both endothelin and angiotensin II receptors, and are useful in the treatment of diseases mediated by endothelin and angiotensin-II and their receptors.
Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis
Daniliuc, Constantin G.,Gilmour, Ryan,Neufeld, Jessica,Sarie, Jér?me C.,Thiehoff, Christian
supporting information, p. 15069 - 15075 (2020/06/17)
The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.
Nickel-catalyzed removal of alkene protecting group of phenols, alcohols via chain walking process
Meng, Chenkai,Niu, Haolin,Ning, Juehan,Wu, Wengang,Yi, Jun
supporting information, (2020/02/04)
An efficient nickel-catalyzed removal of alkene protection group under mild condition with high functional group tolerance through chain walking process has been established. Not only phenolic ethers, but also alcoholic ethers can be tolerated with the retention of stereocenter adjacent to hydroxyl group. The new reaction brings the homoallyl group into a start of new type of protecting group.
Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
supporting information, (2020/05/18)
The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
2-Aryl benzazole derived new class of anti-tubercular compounds: Endowed to eradicate mycobacterium tuberculosis in replicating and non-replicating forms
Datta, Dhrubajyoti,Debnath, Joy,Franzblau, Scott G.,Ghosh, Kalyan Sundar,Hari, Natarajan,Ma, Rui,Rana, Shiwani,Velappan, Anand Babu
, (2020/09/04)
The high mortality rate and the increasing prevalence of Mtb resistance are the major concerns for the Tuberculosis (TB) treatment in this century. To counteract the prevalence of Mtb resistance, we have synthesized 2-aryl benzazole based dual targeted molecules. Compound 9m and 9n were found to be equally active against replicating and non-replicating form of Mtb (MIC(MABA) 1.98 and 1.66 μg/ml; MIC(LORA) 2.06 and 1.59 μg/ml respectively). They arrested the cell division (replicating Mtb) by inhibiting the GTPase activity of FtsZ with IC50 values 45 and 64 μM respectively. They were also capable of kill Mtb in non-replicating form by inhibiting the biosynthesis of menaquinone which was substantiated by the MenG inhibition (IC50 = 11.62 and 7.49 μM respectively) followed by the Vit-K2 rescue study and ATP production assay.
Semiheterogeneous Dual Nickel/Photocatalytic (Thio)etherification Using Carbon Nitrides
Cavedon, Cristian,Madani, Amiera,Seeberger, Peter H.,Pieber, Bartholom?us
supporting information, p. 5331 - 5334 (2019/07/08)
A carbon nitride material can be combined with homogeneous nickel catalysts for light-mediated cross-couplings of aryl bromides with alcohols under mild conditions. The metal-free heterogeneous semiconductor is fully recyclable and couples a broad range of electron-poor aryl bromides with primary and secondary alcohols as well as water. The application for intramolecular reactions and the synthesis of active pharmaceutical ingredients was demonstrated. The catalytic protocol is applicable for the coupling of aryl iodides with thiols as well.
A Structure-Reactivity Relationship of the Tandem Asymmetric Dihydroxylation on a Biologically Relevant Diene: Influence of Remote Stereocenters on Diastereofacial Selectivity
Gill, Daniel M.,Male, Louise,Jones, Alan M.
supporting information, p. 7568 - 7577 (2019/12/11)
The Sharpless asymmetric dihydroxylation (AD) finds widespread use in natural product and drug molecule syntheses, in part, due to its efficiency and predictability. However, the tandem AD of dienes is much less studied, but important in complex molecular synthesis. Herein, a biologically relevant tandem AD is reported, and several anomalies are discovered with the accepted model. These include the formation of unpredicted diastereoisomers, with matched and mismatched stereocenters contradicting the Sharpless mnemonic device. From a structural analysis of the tandem AD, we present a strategy to improve asymmetric induction in sterically hindered alkenes using double diastereodifferentiation from a 9-bond distant stereocenter. A theoretical justification for the unpredicted stereoselectivity, accounting for the influence of steric hindrance and pre-installed chirality, is proposed.
Design and phase transition behavior of siloxane-based monomeric and dimeric liquid crystals bearing cholesteryl mesogenic groups
Katsuki, Kaito,Kaneko, Kosuke,Kaneko, Kimiyoshi,Kato, Riki,Miyamoto, Nobuyoshi,Hanasaki, Tomonori
supporting information, p. 34 - 39 (2019/02/28)
A series of siloxane-based monomeric and dimeric liquid crystals (LCs) bearing cholesteryl mesogenic groups were newly synthesized and their phase transition behavior was investigated by polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction (XRD). All the siloxane-based LCs obtained in this study showed a smectic A phase in a wide temperature range. Among the siloxane-based LCs obtained, only the dimeric LC with a shortest siloxane unit at a central part of a spacer was found to exhibit a chiral nematic phase and a blue phase in addition to the smectic A phase. The difference in the thermal properties of the siloxane-based dimeric LCs was investigated in terms of their conformations. Furthermore, the results obtained for the siloxane-based LCs were discussed with comparing with those of homologues having the normal alkyl chains and spacers.
