Asymmetric catalysis in synthetic strategies for chiral benzothiazepines

Wang, Haifeng; Gu, Shuang‐Xi; Yan, Qiongjiao; Ding, Li; Chen, Fen‐Er

doi:10.1016/j.gresc.2020.05.005

Cited by 46 publications

(17 citation statements)

References 60 publications

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“…Great progress in constructing valuable structures by virtue of various catalytic asymmetric methodologies has been witnessed in recent years. 2–4 Among them, the enantioselective intermolecular [4 + 3] cycloaddition appears to be one of the most straightforward, efficient, and economical approaches to synthesize structurally diverse azepines. 4 Recently, a Pd-catalyzed asymmetric [4 + 3] cycloaddition of trimethylenemethanes (TMM) 5 with benzofuran-derived azadienes 6 has been independently reported by Trost, 7 Shao, 8 and our group, 9 which were applied for the efficient synthesis of benzofuran-fused azepine derivatives with excellent diastereo- and enantioselectivities.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of functionalized azepines via gold and palladium relay catalysis

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Stereoselective synthesis of functionalized azepines via gold and palladium relay catalysis

et al. 2022

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“…The BTZ nucleus has been used as a cardiovascular modulator acting on several G-protein coupled receptors as an antagonist [3], such as the antiarrhythmic (CCK) receptor [4], Angiotensin-Converting Enzyme [5], Angiotensin II receptor [6], etc. Hemodynamic effects, anti-cancer activity [7], and spasmolytic activity [8][9][10], as well as anti-ulcer activity [11], have recently been reported, as had a central nervous system depressant effect [12]. The inhibition of the tyrosine kinase epidemic receptor of growth [13], which is related to the stabilization of the FKBP12 complex skeletal muscle channel-ryanodine receptor, has been reported.…”

Section: Introductionmentioning

confidence: 99%

1,5-Benzothiazepine Derivatives: Green Synthesis, In Silico and In Vitro Evaluation as Anticancer Agents

et al. 2022

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Considering the importance of benzothiazepine pharmacophore, an attempt was carried out to synthesize novel 1,5-benzothiazepine derivatives using polyethylene glycol−400 (PEG−400)-mediated pathways. Initially, different chalcones were synthesized and then subjected to a cyclization step with benzothiazepine in the presence of bleaching clay and PEG−400. PEG−400-mediated synthesis resulted in a yield of more than 95% in less than an hour of reaction time. Synthesized compounds 2a−2j were investigated for their in vitro cytotoxic activity. Moreover, the same compounds were subjected to systematic in silico screening for the identification of target proteins such as human adenosine kinase, glycogen synthase kinase−3β, and human mitogen-activated protein kinase 1. The compounds showed promising results in cytotoxicity assays; among the tested compounds, 2c showed the most potent cytotoxic activity in the liver cancer cell line Hep G−2, with an IC50 of 3.29 ± 0.15 µM, whereas the standard drug IC50 was 4.68 ± 0.17 µM. In the prostate cancer cell line DU−145, the compounds displayed IC50 ranges of 15.42 ± 0.16 to 41.34 ± 0.12 µM, while the standard drug had an IC50 of 21.96 ± 0.15 µM. In terms of structural insights, the halogenated phenyl substitution on the second position of benzothiazepine was found to significantly improve the biological activity. This characteristic feature is supported by the binding patterns on the selected target proteins in docking simulations. In this study, 1,5-benzothiazepines have been identified as potential anticancer agents which can be further exploited for the development of more potent derivatives.

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“…We have previously reported an NHC-catalyzed asymmetric (4 + 2) cycloaddition reaction between 1-methylcyclopropyl-carbaldehyde 1 ( Chi et al, 2011 ; Mu et al, 2020 ; Tong et al, 2021 ; Wang et al, 2021 ) and the cyclic sulfonimides 2 ( Xu et al, 2013 ; Wang et al, 2020a ; Wang et al, 2020b ; Liu et al, 2021 ) to give a variety of multi-functionalized fused cyclic products 3 in moderate to good yields with generally excellent enantio- and diastereoselectivities ( Lv et al, 2021 ) ( Figure 2A ). Indanol-derived NHC catalysts bearing electron-deficient N -substituents were found effective for this transformation.…”

Section: Introductionmentioning

confidence: 99%

An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone

Chen

Pan

et al. 2022

Front. Chem.

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An unprecedented inactivation process of the indanol-derived NHC catalysts bearing N-C6F5 groups is reported. An unexpected multi-cyclic complex product is obtained from the 3-component reaction with the 1-methylcyclopropyl-carbaldehyde, the 2,2,2-trifluoroacetophenone and the NHC catalyst. The absolute structure of the inactivation product is unambiguously assigned via X-ray analysis on its single crystals. The formation of the structurally complex product is rationalized through a multi-step cascade cyclization process.

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Asymmetric catalysis in synthetic strategies for chiral benzothiazepines

Cited by 46 publications

References 60 publications

Stereoselective synthesis of functionalized azepines via gold and palladium relay catalysis

Stereoselective synthesis of functionalized azepines via gold and palladium relay catalysis

1,5-Benzothiazepine Derivatives: Green Synthesis, In Silico and In Vitro Evaluation as Anticancer Agents

An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone

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