121794-40-9Relevant academic research and scientific papers
Synthesis of Axially Chiral 2,2′-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution
Zuo, Ziqing,Kim, Raphael S.,Watson, Donald A.
supporting information, p. 1328 - 1333 (2021/02/01)
We report an asymmetric homocoupling of ortho-(iodo)arylphosphine oxides and ortho-(iodo)arylphosphonates resulting in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates. These products are readily converted to enantioenriched b
Imidazole derivative, preparation method and medical application thereof
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Paragraph 0084-0091, (2021/03/31)
The invention provides a compound as shown in a general formula (I) or a stereoisomer, a deuterated compound, a solvate, a prodrug, a metabolite, a pharmaceutically acceptable salt or eutectic crystalthereof, a preparation method and medical application t
Kinetic Resolution of Tertiary Benzyl Alcohols via Palladium/Chiral Norbornene Cooperative Catalysis
Cheng, Hong-Gang,Ding, Bo,Hong, Xin,Hua, Yu,Liu, Ze-Shui,Xie, Pei-Pei,Zhou, Qianghui
supporting information, p. 12824 - 12828 (2021/05/11)
Herein we report a highly enantioselective kinetic resolution of tertiary benzyl alcohols via palladium/chiral norbornene cooperative catalysis. With simple aryl iodides as the resolution reagent, a wide range of readily available racemic tertiary benzyl alcohols are applicable to this method. Both chiral tertiary benzyl alcohols and benzo[c]chromene products are obtained in good to excellent enantioselectivities (selectivity factor up to 544). The appealing synthetic utility of the obtained enantioenriched tertiary alcohols is demonstrated by the facile preparation of several valuable chiral heterocycles. Preliminary mechanism studies include DFT calculations to explain the origin of enantiodiscrimination and control experiments to uncover the formation of a transient axial chirality during the kinetic resolution step.
An axial-to-axial chirality transfer strategy for atroposelective construction of C–N axial chirality
Chen, Jiangwei,Cheng, Hong-Gang,Hong, Xin,Hua, Yu,Liu, Ze-Shui,Ma, Yuanyuan,Wu, Chenggui,Xie, Pei-Pei,Zhou, Qianghui
supporting information, p. 1917 - 1932 (2021/05/31)
C–N axially chiral skeletons are ubiquitous in bioactive natural products, pharmaceuticals, and chiral ligands. However, their atroposelective synthesis remains a formidable challenge because of their innate low configurational stability compared with tha
Benzoheterocycle substituted phenanthridine quaternary ammonium salt derivative as well as preparation method and application thereof
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Paragraph 0060-0062, (2021/06/12)
The invention discloses a benzoheterocycle substituted phenanthridine quaternary ammonium salt derivative and a preparation method and application thereof, the benzoheterocycle substituted phenanthridine quaternary ammonium salt derivative has a structure
Ni-Catalyzed Reductive Arylcyanation of Alkenes
Li, Hengxu,Chen, Jiachang,Dong, Jueqi,Kong, Wangqing
supporting information, p. 6466 - 6470 (2021/08/23)
We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyano-substituted oxindoles and isoquinoline-1,3-diones and features high functional group tolerance. In addition, an enantioselective version was developed for the construction of enantiomerically enriched 3-cyanomethyl oxindole. This method has also been applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.
Modification of 5-methylphenanthridium from benzothiazoles to indoles as potent FtsZ inhibitors: Broadening the antibacterial spectrum toward vancomycin-resistant enterococci
Chen, Weijin,Ma, Shutao,Song, Di,Zhang, Na,Zhang, Nan,Zhang, Panpan,Zhang, Shenyan
, (2021/08/03)
The death caused by pathogenic bacteria has always been a severe threat to mankind. The prevalence of drug resistance among bacteria underscores an urgent goal for new antibacterial agents with novel mode of action. Here we first designed and synthesized a class of benzothiazolyl-5-methylphenanthridium derivatives and evaluated their antibacterial activity. On this basis, we further designed and synthesized another class of novel indolyl-5-methylphenanthridium derivatives by optimizing the benzothiazolyl-5-methylphenanthridium core and evaluated their antibacterial activity targeting the bacterial cell division protein FtsZ. The results showed that the indolyl-5-methylphenanthridium derivatives had greatly improved activity against various drug-resistant bacterial strains including methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus (VRE). Among them, compound C5 displayed excellent antibacterial activity against susceptible (MIC = 1 μg/mL), methicillin-resistant and clinical isolated S. aureus (MIC = 2 μg/mL). With low hemolytic activity towards mice red blood cells, C5 exhibited good antibacterial effect in vivo in preliminary pharmacodynamic assay. More importantly, C5 was difficult to induce bacterial resistance. Further mechanism studies proved that C5 could inhibit bacterial cell division by promoting FtsZ polymerization, leading to disorderly polymerization and disordered knots. Therefore, our findings suggest that this class of novel indolyl-5-methylphenanthridium derivatives are promising for future antibacterial agents.
Macrofilaricidal Benzimidazole-Benzoxaborole Hybrids as an Approach to the Treatment of River Blindness: Part 2. Ketone Linked Analogs
Carter, David S.,Jacobs, Robert T.,Freund, Yvonne R.,Berry, Pamela W.,Akama, Tsutomu,Easom, Eric E.,Lunde, Christopher S.,Rock, Fernando,Stefanakis, Rianna,Mckerrow, James,Fischer, Chelsea,Bulman, Christina A.,Lim, Kee Chong,Suzuki, Brian M.,Tricoche, Nancy,Sakanari, Judy A.,Lustigman, Sara,Plattner, Jacob J.
, p. 180 - 185 (2020/02/13)
The optimization of a series of benzimidazole-benzoxaborole hybrid molecules linked via a ketone that exhibit good activity against Onchocerca volvulus, a filarial nematode responsible for the disease onchocerciasis, also known as river blindness, is desc
Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position
Cao, Rihui,He, Xuefeng,Li, Yongsu,Liang, Hao,Pan, Bendu,Qiu, Liqin,Subba Reddy, Chitreddy V.,Xia, Wang,Zhang, Yaqi
, p. 966 - 973 (2020/05/14)
Pd-catalyzed asymmetric Suzuki–Miyaura couplings of 3-methyl-2-bromophenylamides, 3-methyl-2-bromo-1-nitrobenzene and 1-naphthaleneboronic acids have been successfully developed and the corresponding axially chiral biaryl compounds were obtained in very high yields (up to 99%) with good enantioselectivities (up to 88% ee) under mild conditions. The chiral-bridged biphenyl monophosphine ligands developed by our group exhibit significant superiority to the naphthyl counterpart MOP in both reactivity and enantioselectivity control. The large steric hindrance from π-conjugated ortho-substituents of the bromobenzene substrates and the Pd···O interaction between carbonyl and palladium seem essential to achieve high enantioselectivity.
Palladium-Catalyzed Stereoselective Aza-Wacker-Heck Cyclization: One-Pot Stepwise Strategy toward Tetracyclic Fused Heterocycles
Chen, Li-Yuan,Chuang, Ta-Hsien,Lai, Chin-Hung,Tang, Rong-Shiow
supporting information, p. 9337 - 9341 (2020/12/21)
Palladium-catalyzed intramolecular tandem cyclization reactions were conducted for the synthesis of densely cis/cis-fused aza-tetracyclic structures. The process involved a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a palladium(0)-catalyzed Heck reaction. The effects of the solvent and benzene substitution pattern on the one-pot, two-step cascade reaction were studied systematically, and a probable mechanism was proposed. Strained pentahydrobenzo[f]cyclopenta[hi]indolizin-6-one and racemic γ-lycorane can also be synthesized rapidly using this palladium-catalyzed aza-Wacker-Heck cyclization reaction.
