4‐Aryl‐2‐ferrocenyl‐ and 2‐Aryl‐4‐ferrocenyl‐2,3‐dihydro‐1,5‐benzothiazepines with Potentially Biological Activities: Synthesis, Characterization, X‐ray Diffraction Studies

Klimova, Elena I.; Vega, Miguel A. Gallardo; García, Jessica J. Sánchez; Flores-Álamo, Marcos; Stivalet, José Manuel Méndez

doi:10.1002/jhet.2519

Cited by 4 publications

(2 citation statements)

References 30 publications

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“…As a continuation of our previous investigations [15] in this field, the present work examines the possibility of synthesizing tetracyclic ferrocenyldihydro-1,5-benzothiazepines starting from 2-ferrocenyl-and 2-anisylmethyliden-1,3-indandiones 1a,b and o-aminothiophenol 2 in the presence of acetic or hydrochloric acid.…”

Section: Introductionmentioning

confidence: 95%

“…The incorporation of a ferrocenyl-substituent into a benzo-1,5-thiazepine molecule will expand the spectrum of valuable characteristics. Ferrocenyl- and structural characteristics [15]. However, The use of 2-ferrocenyl-methyliden-1,3-diones in the synthesis of polycyclic systems with seven-membered heterocycles, such as dihydro-1,5-benzothiazepines and 1,5-benzothiaze-pines, has not been described until now.…”

Section: Introductionmentioning

confidence: 99%

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“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

García¹,

Hernández-Suzan²,

Martínez-Klimova³

et al. 2017

IJOC

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A novel 2-indano[2,3b]-2-ferrocenyl-and 2-indano[2,3b]-2-(p-methoxyphenyl) [1,5]benzo-2,5-dihydrothiazepine 5a,b (addition Michael/cyclization) (~30.32%), indano[2,3b]-2-ferrocenyl-and 2-(p-methoxyphenyl) [1,4] benzothiazine 4a,b (addition "anti-Michael"/cyclization) (~45.43%), respectively, were obtained by the condensation of 2-ferrocenyl-and 2-(p-methoxyphenyl)methyliden-1,3-indandiones 1a,b with o-aminothiophenol 2 in the presence of AcOH and HCl. A new "anti-Michael" addition reaction of 1,4-bis-heteronucleophile 2 into 2-arylmethyliden-1,3-indandiones was reported.As a result of this reaction the product 1a,b was obtained. The structures of the resultant compounds were elucidated by IR, 1 H and 13 C NMR spectroscopy, mass spectrometry, elemental and X-ray diffraction analysis. The in vitro antitumor activity of the obtained products was researched using the following human cancer cell lines: glioblastoma (CNS U-251), prostatic adenocarcinoma (PC-3), chronic myelogenous leukemia (K562), colorectal adenocarcinoma (HCT-15), mammary adenocarcinoma (MCF-7), and small cell lung cancer (SKLU) and the sulforhodamine B (SRB) method. Among these new compounds some thiazine and thiazepine derivatives showed compelling in vitro antitumor effects on cell lines K-562, HCT-15, SKLU-1 and MCF-7.

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Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

García¹,

Hernández-Suzan²,

Martínez-Klimova³

et al. 2017

IJOC

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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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Recent advances in the synthetic chemistry of 1,5‐benzothiazepines: A minireview

Devi

Singh

Monga

2020

Journal of Heterocyclic Chem

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Benzothiazepine, a prominent “drug prejudice core”, is a heterocyclic moiety of immense importance due to its presence in a wide range of bioactive compounds. They act as a primary “biolinker” in diverse synthetic routes to obtain bioactive molecules and serve as important templates in synthetic and medicinal chemistry. They are known to possess a plethora of pharmacological activities, which include Ca2+ channel blockers, CNS acting agents, anti‐HIV, ACE inhibitors, antimicrobial, antifungal, anticancer. Their promising behaviour as drug molecules led the scientific community to develop novel, mild, green, and highly efficient synthetic routes for their synthesis. The conventional synthesis generally involved the condensation of chalcones with 2‐aminothiophenol in the presence of acid/base with high‐temperature heating, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions with mild and green conditions through organocatalysis or other methodologies. In this review, an attempt has been made by authors to summarize (a) Recent developments in the synthetic strategies of 1,5‐benzoathiazepines and its derivatives (b) Conventional methods for the synthesis of 1,5‐benzothiazepines including progress in the green chemistry routes (c) Applications of various metals and organocatalysts to achieve the enantioselective synthesis of title compounds.

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4‐Aryl‐2‐ferrocenyl‐ and 2‐Aryl‐4‐ferrocenyl‐2,3‐dihydro‐1,5‐benzothiazepines with Potentially Biological Activities: Synthesis, Characterization, X‐ray Diffraction Studies

Cited by 4 publications

References 30 publications

“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

“Anti-Michael” and Michael Additions in the Reactions of 2-Arylmethyliden-1,3-Indandiones with 2-Aminothiophenol

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

Recent advances in the synthetic chemistry of 1,5‐benzothiazepines: A minireview

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