Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

Yenupuri, Subhash; Hariharan, Agastyaraju Venkata Lakshmi Narasimha Satyanarayana; Bugata, Bharat Kumar; Nori, Divakara Laxman Somayajulu

doi:10.5155/eurjchem.5.1.138-143.924

Cited by 9 publications

(3 citation statements)

References 21 publications

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“…(E)-3-(3-Fluorophenyl)-1-(1-methyl-1H-pyrrol-2-yl)prop-2en-1-one 1a and (E)-1-(1-methyl-1H-pyrrol-2-yl)-3-(3nitrophenyl)prop-2-en-1-one 1b were synthesized according to the literature, and the spectrum is in good agreement with the reported (Yenupuri, et al, 2014).…”

Section: Experimental Materials and Equipmentsupporting

confidence: 74%

Design, Synthesis, Chemical and Biochemical Insights Into Novel Hybrid Spirooxindole-Based p53-MDM2 Inhibitors With Potential Bcl2 Signaling Attenuation

et al. 2021

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The tumor resistance to p53 activators posed a clinical challenge. Combination studies disclosed that concomitant administration of Bcl2 inhibitors can sensitize the tumor cells and induce apoptosis. In this study, we utilized a rapid synthetic route to synthesize two novel hybrid spirooxindole-based p53-MDM2 inhibitors endowed with Bcl2 signaling attenuation. The adducts mimic the thematic features of the chemically stable potent spiro [3H-indole-3,2′-pyrrolidin]-2(1H)-ones p53-MDM2 inhibitors, while installing a pyrrole ring via a carbonyl spacer inspired by the natural marine or synthetic products that efficiently inhibit Bcl2 family functions. A chemical insight into the two synthesized spirooxindoles including single crystal x-ray diffraction analysis unambiguously confirmed their structures. The synthesized spirooxindoles 2a and 2b were preliminarily tested for cytotoxic activities against normal cells, MDA-MB 231, HepG-2, and Caco-2 via MTT assay. 2b was superior to 5-fluorouracil. Mechanistically, 2b induced apoptosis-dependent anticancer effect (43%) higher than that of 5-fluorouracil (34.95%) in three studied cancer cell lines, activated p53 (47%), downregulated the Bcl2 gene (1.25-fold), and upregulated p21 (2-fold) in the treated cancer cells. Docking simulations declared the possible binding modes of the synthesized compounds within MDM2.

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Section: Experimental Materials and Equipmentsupporting

confidence: 74%

Design, Synthesis, Chemical and Biochemical Insights Into Novel Hybrid Spirooxindole-Based p53-MDM2 Inhibitors With Potential Bcl2 Signaling Attenuation

et al. 2021

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“…Regardless of the advancement in antimicrobial therapy, several problems remain to be solved for the majority of accessible antimicrobial drugs. 1,5‐Benzothiazepines are recognized to show antimicrobial activities against various bacterial and fungal strains like Bacillus substilis , Bacillus pumilus , Staphylococcus aureus , Staphylococcus epidermidis , Klebsiella aerogenes , Fusarium oxysporum , Candida krusei , Escherichia coli , Pseudomonas aeruginosa , Klebsiella pneumoniae , Aspergillus fumigatus , Salmonella Typhi, Candida violaceum , Aspergillus niger , Aspergillus flavus , Candida albicans , and Trichophyton rubrum. Considering the aforementioned facts, we carried out the in vitro antimicrobial screening of all the synthesized indane‐based 1,5‐benzothiazepines ( 5 ) against two Gram‐positive bacterial strains, namely, Bacillus subtilis (MTCC 441) and S. epidermidis (MTCC 6880); two Gram‐negative bacterial strains, namely, E. coli (MTCC 1652) and P. aeruginosa (MTCC 424); and two fungal strains, namely, C. albicans (MTCC 227) and A. niger (MTCC 8189) by using serial dilution method as explained earlier by Mor et al .…”

Section: Resultsmentioning

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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“…The mixture of crude chalcone (6) and oaminothiophenol (1) was irradiated under microwave in the presence of acetic acid and piperidine as co-catalyst in DMF to afford the final products in satisfactory yields (Scheme 2). [30] Mor et al reported an environmentally benign approach for the synthesis of indane appended 1,5-benzothiazepine derivatives (11) from indane-based chalcones, that is, 2-arylidene-3-phenyl-2,3-dihydro-1H-inden-1-ones (10). The required intermediate chalcones were prepared via Claisen Schmidt condensation of 3-phenyl-2,3-dihydro1H-inden-1-one (8) with appropriate benzaldehydes (9).…”

Section: Synthesis From Chalcones Using Eco-friendly Approachesmentioning

confidence: 99%

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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Microwave assisted synthesis and biological evaluation of a series of 1,5-benzothiazepines as potential cytotoxic and antimicrobial agents

Cited by 9 publications

References 21 publications

Design, Synthesis, Chemical and Biochemical Insights Into Novel Hybrid Spirooxindole-Based p53-MDM2 Inhibitors With Potential Bcl2 Signaling Attenuation

Design, Synthesis, Chemical and Biochemical Insights Into Novel Hybrid Spirooxindole-Based p53-MDM2 Inhibitors With Potential Bcl2 Signaling Attenuation

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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