Synthesis, characterization, antimicrobial, anticancer, and antituberculosis activity of some new pyrazole, isoxazole, pyrimidine and benzodiazepine derivatives containing thiochromeno and benzothiepino moieties

Palanisamy, P.; Jenniefer, Samson Jegan; Muthiah, Packianathan Thomas; Kumaresan, S.

doi:10.1039/c3ra42283f

Cited by 26 publications

(15 citation statements)

References 46 publications

(65 reference statements)

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“…For example, series of 1,5‐benzodiazepines were described by Pandaram et al . as potent antimicrobial agents . Therefore, the research on the synthesis and antimicrobial activity of 1,5‐benzodiazepines has become a popular topic.…”

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confidence: 99%

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Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Zhenfang

Zhang

et al. 2016

Chem Biol Drug Des

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A series of novel 1,5-benzodiazepine derivatives were rationally designed and synthesized following the principle of the superposition of bioactive substructures by the combination of 1,5-benzodiazepine, pyridine (phenyl), and an ester group. The structures of the target compounds were determined by (1) H NMR, (13) C NMR, MS, IR, and elemental analysis. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi C. neoformans, C. neoformans clinical isolates (ATCC 32264), C. albicans (ATCC 10231), Gram-negative bacterium E. coli (ATCC 44752), and Gram-positive bacterium S. aureus (ATCC 25923). The results of the bioactive assay demonstrated that most of the tested compounds exhibited variable inhibitory effects on the growth of the tested microorganisms. All the active compounds showed better antifungal activity than antibacterial activity. Notably, compound 2b displayed the highest activity (MIC = 30 μg/mL) against C. neoformans and (MIC = 31 μg/mL) against C. neoformans clinical isolates. In addition, compound 2a also showed excellent activity against C. neoformans and C. neoformans clinical isolates with minimum inhibitory concentration of 35 and 36 μg/mL, respectively. Compounds 2a and 2b were further studied by evaluating their cytotoxicities, and the results showed that they have relatively low level cytotoxicity for BV2 and 293T cell. Preliminary structure-activity relationship study on three diverse sets (C-2, C-3, and C-8 positions) of 1,5-benzodiazepines was performed. The results revealed that the presence of a -CH3 group at the C-8 position had a positive effect on the inhibitory activity of these compounds. Additionally, the 2-pyridyl group at the C-2 position may be a pharmacophore and -COOC2 H5 at C-3 position is the best substituent for the maintenance of antimicrobial activities.

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confidence: 99%

“…To date, a significant number of 1,5-benzodiazepines analogs with antimicrobial activity has been synthesized (2)(3)(4)(5). For example, series of 1,5-benzodiazepines were described by Pandaram et al as potent antimicrobial agents (6). Therefore, the research on the synthesis and antimicrobial activity of 1,5-benzodiazepines has become a popular topic.…”

mentioning

confidence: 99%

Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Zhenfang

Zhang

et al. 2016

Chem Biol Drug Des

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“…The synthesis of 2-aminothiazoles derivatives has several problems including low yield, harsh reactions, difficult isolation procedures, use of expensive catalysts [4][5][6] and so on. Thiazole derivatives are significantly important heterocyclic compounds which exhibit a wide range of biological activities such as fungicidal [7], bactericidal [8], cardiovascular [9], antitumor [10], anti-allergic [11], central nervous system stimulate [12,13] and antipyretic [14]. Due to the broad range of their applications, 2-aminothiazoles have been used in the synthesis of polymers [15,16].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Biological Activities of Some Heterocyclic Compounds Derivatives from 2-Aminothiazoles

Al-Rammahi¹

2018

Nano BioMed ENG

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In the current investigation, two series of 2-amino thiazole derivatives were prepared. The first series involved synthesis of (Z)-3-(thiazol-2-ylimino)indolin-2-one (A1) as Schiff base derivatives of 2-amino thiazole and isatin, then synthesis of compounds A5, A6 and A7 as five membered rings (imidazolidins) by using different amino acids, and synthesis of compounds A3 and A4 as seven membered rings (1,3-oxazepine-di-one) by using maleic and phthalic anhydrides respectively. In the second series, 2-amino thiazole was treated with acetyl acetone to form (2E,4E)-N2,N4-di(thiazol-2-yl) pentane-2,4-diimine (A2) as di-Schiff base derivatives, and finally the preparation of imidazolidin (A8) by using 2 mol of tyrosine and preparation of tetrazole derivative (A9) by using 2 mol of sodium azide. The biological study for the above two series indicated that both gram-negative and grampositive activities were noticed.

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“…Addition of lipophilic moiety at position 2 as furan‐2‐yl to quinazolin‐4‐one scaffold afforded the active anticancer agent IV , the previously reported work has proved that changing the para position of 3‐phenyl moiety has a great impact on anticancer activity , as a result we synthesized the quinazolin‐4‐one scaffold having a lipophilic furan moiety at position 2 with various substituents at the 4 position of the aryl moiety to study these structural changes in correlation to the activity. It also was of our interest to substitute the 4 position of the 3‐phenyl with biologically active anticancer moieties as chalcone , pyrazole , isoxazole , and pyrimidine .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of 2‐(Furan‐2‐yl)quinazolin‐4‐one Derivatives as Potential Antiproliferative Agents

Ahmed

Belal

2015

Archiv der Pharmazie

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Fifteen new derivatives of quinazolin-4-one bearing the 2-furyl moiety at position 2 and a substituted phenyl moiety at position 3 were designed and synthesized to be evaluated as cytotoxic agents. Their chemical structures were confirmed by spectral and elemental analysis; cytotoxic activity evaluation was performed against HEPG2, HCT116, and MCF7 cancer cell lines using the sulforhodamine-B assay. All the tested compounds except 6a showed high potency against the HEPG2 cancer cell line (IC50 8-101 nM/mL); 11 compounds out of 15 proved to be potent against HCT116 cells (IC50 3-49 nM/mL), also 11 of the tested compounds showed high potency against MCF7 cells with IC50 values ranging from 7 to 63 nM/mL. The rest of the tested compounds showed IC50 values of more than 100 nM/mL. Compounds 3e and 4d are the most active compounds against HEPG2 cells; in addition, 3e is the most active compound against MCF7 cells. Also, compounds 4a, 3a, and 3b are the most active compounds against HCT116 cells. Compounds 3a, 3b, 3e, 4a, and 4d were also evaluated for their inhibitory activity against the EGFR tyrosine kinase (EGFR-TK) and showed a percentage inhibitory activity ranging from 53 to 84%. The most potent EGFR-TK inhibitors, 3a (84%), 3b (75%), and 3e (60%), were docked into the ATP binding site of the EGFR to explore their binding mode and possible interactions.

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Synthesis, characterization, antimicrobial, anticancer, and antituberculosis activity of some new pyrazole, isoxazole, pyrimidine and benzodiazepine derivatives containing thiochromeno and benzothiepino moieties

Cited by 26 publications

References 46 publications

Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5‐Benzodiazepine Derivatives as Potential Antimicrobial Agents

Preparation and Biological Activities of Some Heterocyclic Compounds Derivatives from 2-Aminothiazoles

Design, Synthesis, and Molecular Docking Studies of 2‐(Furan‐2‐yl)quinazolin‐4‐one Derivatives as Potential Antiproliferative Agents

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