1132669-90-9Relevant articles and documents
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases
Yan, Yu-Hang,Li, Zhao-Feng,Ning, Xiang-Li,Deng, Ji,Yu, Jun-Lin,Luo, Yubin,Wang, Zhenling,Li, Guo,Li, Guo-Bo,Xiao, You-Cai
supporting information, (2021/04/12)
The production of β-lactamases represents the main cause of resistance to clinically important β-lactam antibiotics. Boron containing compounds have been demonstrated as promising broad-spectrum β-lactamase inhibitors to combat β-lactam resistance. Here we report a series of 3-aryl substituted benzoxaborole derivatives, which manifested broad-spectrum inhibition to representative serine-β-lactamases (SBLs) and metallo-β-lactamases (MBLs). The most potent inhibitor 9f displayed an IC50 value of 86 nM to KPC-2 SBL and micromolar inhibitory activity towards other tested enzymes. Cell-based assays further revealed that 9f was able to significantly reduce the MICs of meropenem in clinically isolated KPC-2-producing bacterial strains and it showed no apparent toxicity in HEK293T cells.
Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance
Chen, Fener,Chen, Xiao-Pan,Deng, Ji,Li, Gen,Li, Guo-Bo,Schofield, Christopher J.,Xiao, You-Cai,Yan, Yu-Hang,Yu, Jun-Lin,Zhu, Kai-Rong,Brem, Jürgen
supporting information, p. 7709 - 7712 (2021/08/09)
Chiral 3-substituted benzoxaboroles were designed as carbapenemase inhibitors and efficiently synthesisedviaasymmetric Morita-Baylis-Hillman reaction. Some of the benzoxaboroles were potent inhibitors of clinically relevant carbapenemases and restored the activity of meropenem in bacteria harbouring these enzymes. Crystallographic analyses validate the proposed mechanism of binding to carbapenemases,i.e.in a manner relating to their antibiotic substrates. The results illustrate how combining a structure-based design approach with asymmetric catalysis can efficiently lead to potent β-lactamase inhibitors and provide a starting point to develop drugs combatting carbapenemases.
Transition-metal-free, one-pot synthesis of benzoxaboroles from: O -bromobenzaldehydes via visible-light-promoted borylation
Chen, Jianchao,Hu, Yanjun,Jia, Xingxing,Luo, Jinghan,Sun, Tiemin
, p. 10455 - 10459 (2021/12/17)
A novel and simple one-pot stepwise method to synthesize benzoxaboroles was demonstrated. This step-by-step synthetic method includes photocatalytic boronization with phenothiazine as a photocatalyst and sequential water-induced reduction in the presence of bis(pinacolato)diboron. A series of o-bromobenzaldehydes were well-tolerated under the standard conditions. In addition, this method has been successfully applied in the synthesis of the anti-tuberculosis candidate drug GSK 3036656 and anti-fungal drug tavaborole. This journal is
Imidazole-containing condensed tricyclic compound and application thereof
-
Paragraph 0192, (2018/03/01)
The invention discloses an imidazole-containing condensed tricyclic compound adopting the structure as shown in the formula (I) or pharmaceutically acceptable salts, stereisomers or prodrug molecules thereof. The imidazole-containing condensed tricyclic compound has the IDO1 activity regulation function, can enhance T-cell activation through blocking immune checkpoints IDO1, is used for treating IDO1-mediated immunosuppression, and therefore, can become an effective medicine for treating malignant tumors. When used together with checkpoint protein anti-body drugs or other anti-cancer drugs, the imidazole-containing condensed tricyclic compound can enhance the anti-cancer effect. Meanwhile, the imidazole-containing condensed tricyclic compound has the potential of effectively treating IDO1 abnormity related immunosuppressive diseases and has a high application value.
Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines
Bisht, Ranjana,Chattopadhyay, Buddhadeb
, p. 84 - 87 (2016/01/25)
The ligand-enabled development of ortho and meta C-H borylation of aromatic aldehydes is reported. It was envisaged that while ortho borylation could be achieved using tert-butylamine as the traceless protecting/directing group, meta borylation proceeds via an electrostatic interaction and a secondary interaction between the ligand of the catalyst and the substrate. These ligand-substrate electrostatic interactions and secondary B-N interactions provide an unprecedented controlling factor for meta-selective C-H activation/borylation.
Syntheses of macrocyclic bis(bibenzyl) compounds derived from perrottetin e
Speicher, Andreas,Groh, Matthias,Hennrich, Markus,Huynh, Anh-Minh
, p. 6760 - 6778 (2011/03/18)
Macrocyclic bis(bibenzyl) compounds are natural products from liverworts and are of growing interest due to recent reports on new isolated compounds and on their remarkable biological activities. We report here on a flexible and general approach to the to
Synthesis and biological evaluations of P4-benzoxaborole-substituted macrocyclic inhibitors of HCV NS3 protease
Ding, Charles Z.,Zhang, Yong-Kang,Li, Xianfeng,Liu, Yang,Zhang, Suoming,Zhou, Yasheen,Plattner, Jacob J.,Baker, Stephen J.,Liu, Liang,Duan, Maosheng,Jarvest, Richard L.,Ji, Jingjing,Kazmierski, Wieslaw M.,Tallant, Matthew D.,Wright, Lois L.,Smith, Gary K.,Crosby, Renae M.,Wang, Amy A.,Ni, Zhi-Jie,Zou, Wuxin,Wright, Jon
scheme or table, p. 7317 - 7322 (2011/01/12)
We disclose here a series of P4-benzoxaborole-substituted macrocyclic HCV protease inhibitors. These inhibitors are potent against HCV NS3 protease, their anti-HCV replicon potencies are largely impacted by substitutions on benzoxaborole ring system and P2 groups. P2 2-thiazole-isoquinoline provides best replicon potency. The in vitro SAR studies and in vivo PK evaluations of selected compounds are described herein.
A synthesis-driven structure revision of 'plagiochin E', a highly bioactive bisbibenzyl
Speicher, Andreas,Groh, Matthias,Zapp, Josef,Schauml?ffel, Anu,Knauer, Michael,Bringmann, Gerhard
scheme or table, p. 1852 - 1858 (2009/12/05)
Recently, a bisbibenzyl named plagiochin E showing remarkable antifungal and antitumor activities was isolated from Marchantia polymorpha, a liverwort. The total synthesis of the proposed structure for plagiochin E and of two structurally and biosynthetic
Rhodium-catalyzed tandem cyclization: Formation of 1H-indenes and 1-alkylideneindans from arylboronate esters in aqueous media
Lautens, Mark,Marquardt, Tzvetelina
, p. 4607 - 4614 (2007/10/03)
Arylboronate esters bearing a pendant Michael-type acceptor olefin or acetylene linkage undergo transmetalation with a rhodium-based catalytic complex to generate a functionalized organorhodium intermediate which can cyclize onto nonterminal acetylenes in
