Synthesis, in vitro antimicrobial, antiproliferative, and QSAR studies of N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides

Kumar, Harsh; Kumar, Pradeep; Narasimhan, Balasubramanian; Ramasamy, Kalavathy; Mani, Vasudevan; Mishra, Rakesh K.; Majeed, Abu Bakar Abdul

doi:10.1007/s00044-012-0181-0

Cited by 10 publications

(7 citation statements)

References 33 publications

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“…Schiff 's bases (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) were obtained by treating terephthalaldehyde and various substituted amines/anilines by taking acetic acid (glacial) as catalyst. Further compounds 1-19 were treated with thioglycolic acid using a small quantity of zinc chloride as catalyst to obtain intermediates 4-(4-oxo-3-substitutedaryl/alkylthiazolidin-2-yl)benzaldehyde (A1-A19).…”

Section: Resultsmentioning

confidence: 99%

“…Step 2: Synthesis of (E)-4-((substitutedaryl/alkylimino)methyl)benzaldehyde (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19): To a solution of terephthalaldehyde (0.01 mol) in ethanol (25 mL), various substituted amines/anilines in equimolar amount were added using acetic acid (glacial) as a catalyst and refluxing was done for 6-15 h. The reaction mixture was then allowed to cool to obtain solid mass which was further recrystallized from methanol to give intermediate Schiff 's bases (1-19) [37].…”

Section: Synthetic Steps Of Schemementioning

confidence: 99%

“…The World Health Organization (WHO) reports indicate that the microbial drug resistance (MDR) caused due to continuous use of presently available antibiotics and the development of resistance against presently available anticancer drugs is the major concern for human life worldwide now a days [1,2]. The clinical effectiveness of currently using antibiotics against most of the MDR strains, viz.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, biological evaluation and in-silico ADME studies of novel series of thiazolidin-2,4-dione derivatives as antimicrobial, antioxidant and anticancer agents

Kumar

et al. 2022

BMC Chemistry

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Background A novel series of thiazolidine-2,4-dione molecules was derived and their chemical structures were established using physiochemical parameters and spectral techniques (1H-NMR, IR, MS etc.). The synthesized molecule were then evaluated for their antioxidant, anticancer and antimicrobial potential. Results and discussion Serial tube dilution method was employed to evaluate the antimicrobial potential against selected fungal and bacterial strains by taking fluconazole and cefadroxil as reference antifungal and antibacterial drugs respectively. 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging activity was used to assess the antioxidant potential of the synthesized analogues. Further, the anticancer potential of the selected molecules was assessed against DU-145 cancer cell lines using MTT assay. The drug-likeness was also evaluated by studying in-silico ADME parameters of the synthesized analogues. Conclusion In antioxidant evaluation studies, the analogue H5 with IC50 = 14.85 μg/mL was found to be the most active molecule. The antimicrobial evaluation outcomes suggested that the molecules H5, H13, H15 and H18 possessed moderate to promising activity against the selected species of microbial strains having MIC range 7.3 µM to 26.3 µM. The results of anticancer evaluation revealed that all the screened derivatives possess mild anticancer potential. The in-silico ADME studies revealed that all the compounds were found to be drug-like.

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Section: Resultsmentioning

confidence: 99%

Section: Synthetic Steps Of Schemementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, biological evaluation and in-silico ADME studies of novel series of thiazolidin-2,4-dione derivatives as antimicrobial, antioxidant and anticancer agents

Kumar

et al. 2022

BMC Chemistry

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“…Thionyl chloride (0.3 mol) was added to 4-(2-(1 H -benzo[ d ]imidazol-2-ylthio) acetamido) benzoic acid ( b , 0.25 mol) and the mixture were refluxed for 2–3 h . The excess of thionyl chloride was removed by distillation [17].…”

Section: Methodsmentioning

confidence: 99%

4-(2-(1H-Benzo[d]imidazol-2-ylthio)acetamido)-N-(substituted phenyl)benzamides: design, synthesis and biological evaluation

et al. 2019

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Background Dihydrofolate reductase (DHFR) is an important target for antimetabolite class of antimicrobials because it participates in purine synthesis. 2-mercaptobenzimidazole (2MBI) has similar structural features as purine nucleotides. Given that benzimidazole and similar heteroaromatics have been broadly examined for their anticancer potential, so, we hereby report the design, synthesis and biological studies (i.e. antimicrobial and anticancer studies) of 2MBI derivatives. Methodology The antimicrobial activity of synthesized 2MBI derivatives were evaluated against Gram positive and Gram negative bacterial species as well as fungal species by tube dilution technique whereas their anticancer activity was assessed against human colorectal carcinoma cell line (HCT116) by Sulforhodamine B (SRB) assay. They were also structurally characterized by IR, NMR, MS and elemental analyses. Results, discussion and conclusion The antimicrobial activity findings revealed that compound N1 (MIC bs,st, ca = 1.27, 2.54, 1.27 µM), N8 (MIC ec = 1.43 µM), N22 (MIC kp,an = 2.60 µM), N23 and N25 (MIC sa = 2.65 µM) exhibited significant antimicrobial effects against tested strains, i.e. Gram-positive, Gram-negative (bacterial) and fungal strains. The anticancer screening results demonstrated that compounds N9 , N18 (IC 50 = 5.85, 4.53 µM) were the most potent compounds against cancer cell line (HCT116) even more than 5-FU, the standard drug (IC 50 = 9.99 µM).

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“…A mixture of thionyl chloride (0.3 mol) and 3-(2-(1 H -benzo[ d ]imidazol-2-ylthio)acetamido) benzoic acid (int- II , 0.25 mol) was refluxed for 2 h. The excess of thionyl chloride was removed by distillation [21].…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis and therapeutic potential of 3-(2-(1H-benzo[d]imidazol-2-ylthio)acetamido)-N-(substituted phenyl)benzamide analogues

Tahlan

Ramasamy

Lim

et al. 2018

Chemistry Central Journal

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BackgroundThe emergence of bacterial resistance is a major public health problem. It is essential to develop and synthesize new therapeutic agents with better activity. The mode of actions of certain newly developed antimicrobial agents, however, exhibited very limited effect in treating life threatening systemic infections. Therefore, the advancement of multi-potent and efficient antimicrobial agents is crucial to overcome the increased multi-drug resistance of bacteria and fungi. Cancer, which remains as one of the primary causes of deaths and is commonly treated by chemotherapeutic agents, is also in need of novel and efficacious agents to treat resistant cases. As such, a sequence of novel substituted benzamides was designed, synthesized and evaluated for their antimicrobial and anticancer activities.MethodologyAll synthesized compounds were characterized by IR, NMR, Mass and elemental analysis followed by in vitro antimicrobial studies against Gram-positive (Staphylococcus aureus), Gram-negative (Salmonella typhi and Klebsiella pneumoniae) bacterial and fungal (Candida albicans and Aspergillus niger) strains by the tube dilution method. The in vitro anticancer evaluation was carried out against the human colorectal carcinoma cell line (HCT116), using the Sulforhodamine B assay.Results, discussion and conclusionCompound W6 (MICsa, st, kp = 5.19 µM) emerged as a significant antibacterial agent against all tested bacterial strains i.e. Gram-positive (S. aureus), Gram-negative (S. typhi, K. pneumoniae) while compound W1 (MICca, an = 5.08 µM) was most potent against fungal strains (A. niger and C. albicans) and comparable to fluconazole (MIC = 8.16 µM). The anticancer screening demonstrated that compound W17 (IC50 = 4.12 µM) was most potent amongst the synthesized compounds and also more potent than the standard drug 5-FU (IC50 = 7.69 µM).

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Synthesis, in vitro antimicrobial, antiproliferative, and QSAR studies of N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides

Cited by 10 publications

References 33 publications

Synthesis, biological evaluation and in-silico ADME studies of novel series of thiazolidin-2,4-dione derivatives as antimicrobial, antioxidant and anticancer agents

Synthesis, biological evaluation and in-silico ADME studies of novel series of thiazolidin-2,4-dione derivatives as antimicrobial, antioxidant and anticancer agents

4-(2-(1H-Benzo[d]imidazol-2-ylthio)acetamido)-N-(substituted phenyl)benzamides: design, synthesis and biological evaluation

Design, synthesis and therapeutic potential of 3-(2-(1H-benzo[d]imidazol-2-ylthio)acetamido)-N-(substituted phenyl)benzamide analogues

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