Convenient synthesis, anticancer evaluation and QSAR studies of some thiazole tethered indenopyrazoles

Mor, Satbir; Nagoria, Savita; Kumar, Ashwani; Monga, Jitender; Lohan, Sandeep

doi:10.1007/s00044-016-1528-8

Cited by 15 publications

(10 citation statements)

References 67 publications

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“…In the recent years, indeno-fused heterocycles are recognized as important frameworks with a broad spectrum of pharmacological properties. Among them, indenopyrazoles have gained substantial attention due to their wide range of biological activities such as antitubercular (Ahsan et al 2011), tyrosine kinase inhibitors , CNS agents (Lemke et al 1978), antioxidant activity , non-steroidal anti-inflammatory drugs (Lemke et al 1989), anticancer (Mor et al 2016), antimicrobial (Shareef et al 2019), anti-HIV and anticonvulsant activities (Ahsan et al 2012), and cyclin-dependent kinase (CDK) inhibitors (Singh et al 2006). Moreover, methyl 3-((6-methoxy-1,4dihydroindeno [1,2-c]pyrazol-3-yl)amino)benzoate was the first indenopyrazole that was reported as a Tubulin Polymerization Inhibitor (Minegishi et al 2015).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

Mor

Sindhu

2019

Med Chem Res

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We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a-o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1 H NMR, 13 C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a-o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC 50 = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC 50 = 9.35 μg/mL) and 4i (IC 50 = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC 50 = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

Mor

Sindhu

2019

Med Chem Res

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“…Keeping in view of the above facts, and in continuation of our studies on indenopyrazoles , herein, we report synthesis, biological activities (antimicrobial and antioxidant), and docking studies of several N ‐thiazolyl hydrazones ( 3a – h ) and their cyclic analogues, that is, indenopyrazolones ( 4a – h ) (Fig. ).…”

Section: Introductionmentioning

confidence: 90%

“…Among them, pyrazoles are usually the core fragment of pharmaceutical drugs such as deracoxib, celecoxib, oxyphenbutazone, phenylbutazone, kebuzone, and feprazone with reduced ulcer genic side effects . Among the pyrazoles, in particular, indeno[1,2‐ c ]pyrazol‐4‐ones are an important class of heterocycles because of pervasiveness of biological activities . For instance, indenopyrazoles have been recognized as potential cyclin‐dependent kinase inhibitors , antitubercular agents , nonsteroidal anti‐inflammatory drugs , CNS agents , antidepressants , tyrosine kinase inhibitors , cytotoxic activity , and checkpoint kinase inhibitors .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking Studies of Some N‐thiazolyl Hydrazones and Indenopyrazolones

Mor

Sindhu

Nagoria

et al. 2019

Journal of Heterocyclic Chem

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Two new series of N‐thiazolyl hydrazones (3a–h) and indenopyrazolones (4a–h) were synthesized by the reaction of various 2‐acyl‐(1H)‐indene‐1,3(2H)‐diones, thiosemicarbazide, and phenacyl bromide/substituted phenacyl bromides. The in vitro antimicrobial activity of these synthesized compounds was assayed against four bacteria, namely, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, and two fungi, namely, Candida albicans and Aspergillus niger, by employing serial dilution method. Ciprofloxacin and fluconazole were used as antibacterial and antifungal reference drugs, respectively. Results of antimicrobial assay showed that the tested compounds have broad range of activity. The compounds 3h and 4a against C. albicans displayed more potency than fluconazole whereas 3b and 3c against B. subtilis showed activity comparable with ciprofloxacin. The synthesized indenopyrazolones (4a–h) were evaluated for their in vitro antioxidant activity by 2,2‐diphenyl‐1‐picrylhydrazyl radical scavenging assay using ascorbic acid as reference. Compound 4b exhibited the highest 2,2‐diphenyl‐1‐picrylhydrazyl radical scavenging with IC50 value 33.14 μg/mL. The observed results of antimicrobial activity were supported by molecular docking study performed to understand the binding interaction of hydrazones (3a–h) and indenopyrazolones (4a–h) with lanosterol 14α‐demethylase.

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“…Moreover, indenopyrazole derivatives are among the compounds that have attracted increased attention in recent years because of their biological activities and the potential for application as pharmacological agents. Several studies have shown that indenopyrazoles have bioactive properties such as antibacterial, anticancer, cytostatic, antitubercular, and inhibition on enzymes involved in the cell cycle . So, studies on the synthesis and activities of new indenoprirazole derivatives are increasing in the literature day by day …”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel indenopyrazole derivatives

Gezegen

Tutar

Hepokur

et al. 2019

J Biochem & Molecular Tox

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A series of novel indenopyrazole derivatives 2a-j and 3a-j were synthesized from the reaction of 1-(4-(hydroxy(1-oxo-1,3-dihydro-2H-inden-2-ylidene)methyl)phenyl)-3phenylurea derivatives 1a-j with hydrazine and phenylhydrazine, respectively. The obtained novel indenopyrazoles (2a-j and 3a-j) were evaluated for anticancer activity against HeLa and C6 cell lines. Antiproliferative activity was determined by the BrdU proliferation ELISA assay; 2a, 2b, 2d, 2h, and 3h were found to be the most active compounds. The compounds were also screened for antimicrobial activity, and all compounds showed moderate activity against used microorganisms.

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Convenient synthesis, anticancer evaluation and QSAR studies of some thiazole tethered indenopyrazoles

Cited by 15 publications

References 67 publications

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

Synthesis, Biological Evaluation, and Molecular Docking Studies of Some N‐thiazolyl Hydrazones and Indenopyrazolones

Synthesis and biological evaluation of novel indenopyrazole derivatives

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