Synthesis of novel β-lactam-fused 1,5-benzothiazepine derivatives bearing quinoline moiety

Zeng, Yongming; Zeng, Hehua; Zhang, Hongxi; Liu, Geng; Zhao, Xiufeng; Cheng, Jian‐Wen

doi:10.1080/10426507.2014.999859

Cited by 4 publications

(2 citation statements)

References 31 publications

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“…Additionally, thiadiazepines are expected to play a vital role in the biological system. Recently, researchers have increased the focus towards the synthesis and biological importance of thiadiazepines [12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

et al. 2019

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A series of triazolo-thiadiazepines 4a–k were synthesized with excellent yields using dehydrated PTSA as a catalyst in toluene. Two triazolo-thiadiazines were obtained; 8a was formed directly by reflux in ethanol, whereas, PTSA promoted the formation of 8b. The molecular structure of the formed triazolo-thiadiazepines is identical to the imine-form 4a–k and not the enamine-tautomer 6a–k. The structures of the newly synthesized triazolo-thiadiazepines 4a–k and triazolo-thiadiazines 8a–b were elucidated using NMR (1H, and 13C), 2D NMR, HRMS, and X-ray single crystal. Furthermore, 4a was deduced using X-ray single crystal diffraction analysis. These new thiadiazepine hits represent an optimized series of previously synthesized indole-triazole derivatives for the inhibition of EGFR. The cytotoxicity activity against two cancer cell lines including human liver cancer (HEPG-2) and breast cancer (MCF-7) was promising, with IC50 between 12.9 to 44.6 µg/mL and 14.7 to 48.7 µg/mL for the tested cancer cell lines respectively, compared to doxorubicin (IC50 4.0 µg/mL). Docking studies revealed that the thiadiazepine scaffold presented a suitable anchor, allowing good interaction of the various binding groups with the enzyme binding regions and sub-pockets.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

et al. 2019

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“…The pharmaceutical prominence of 1,5‐benzothiazepines has encouraged the researchers all over the world, and many reviews have been documented in the literature, which compiled various aspects related to their synthetic advances and biological importance. Consequently, several synthetic protocols have been developed to access this biodynamic skeleton . The most convenient method for the synthesis of 1,5‐benzothiazepines involves the condensation of α,β‐unsaturated carbonyl compounds and 2‐aminobenzenethiols .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Indane‐Based 1,5‐Benzothiazepines Derived from 3‐Phenyl‐2,3‐dihydro‐1H‐inden‐1‐one and Antimicrobial Studies Thereof

Mor

Nagoria

Sindhu

et al. 2017

Journal of Heterocyclic Chem

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In the present study, a series of 20 indane‐based 1,5‐benzothiazepines (5a–t) has been prepared derived from 3‐phenyl‐2,3‐dihydro‐1H‐inden‐1‐one (1). All the synthesized 1,5‐benzothiazepines (5a–t) were screened for their in vitro antimicrobial activities against four bacteria [Bacillus subtilis (MTCC 441), Staphylococcus epidermidis (MTCC 6880), Escherichia coli (MTCC 1652), and Pseudomonas aeruginosa (MTCC 424)] and two fungi [Candida albicans (MTCC 227) and Aspergillus niger (MTCC 8189)]. Among all the tested derivatives, 5n and 5o against E. coli displayed more inhibitory activity than that of the reference drug, ciprofloxacin, while the derivatives 5c, 5m–o, 5s, and 5t against C. albicans, and 5d, 5e, 5n, 5o, 5s, and 5t against A. niger were found to be more potent than the standard drug, that is, fluconazole.

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Seven-Membered Rings

Meyer

Bissember

Hyland

et al. 2017

Progress in Heterocyclic Chemistry

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Synthesis of novel β-lactam-fused 1,5-benzothiazepine derivatives bearing quinoline moiety

Cited by 4 publications

References 31 publications

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

Synthesis of Indane‐Based 1,5‐Benzothiazepines Derived from 3‐Phenyl‐2,3‐dihydro‐1H‐inden‐1‐one and Antimicrobial Studies Thereof

Seven-Membered Rings

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