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Design and Synthesis of New 6-Nitro and 6-Amino-3,3a,4,5-Tetrahydro-2H-Benzo[g]indazole Derivatives: Antiproliferative and Antibacterial Activity.

ABSTRACT: New substituted benzo[g]indazoles functionalized with a 6-nitro and 6-amino groups have been synthesized by the reaction of benzylidene tetralones with hydrazine in acetic acid. The resulting conformationally-constrained compounds were evaluated for their antiproliferative activity against selected cancer cell lines. The nitro-based indazoles 11a, 11b, 12a and 12b have shown IC50 values between 5-15 ?M against the lung carcinoma cell line NCI-H460. Moreover, the nitro compounds were tested for antibacterial activity where compounds 12a and 13b have shown MIC values of 250 and 62.5 ?g/mL against N. gonorrhoeae with no hemolytic activity in human red blood cells (RBC).

SUBMITTER: Cuartas V

PROVIDER: S-EPMC6930490 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Design and Synthesis of New 6-Nitro and 6-Amino-3,3a,4,5-Tetrahydro-2H-Benzo[g]indazole Derivatives: Antiproliferative and Antibacterial Activity.

Cuartas Viviana V Crespo María Del Pilar MDP Priego Eva-María EM Persoons Leentje L Daelemans Dirk D Camarasa María-José MJ Insuasty Braulio B Pérez-Pérez María-Jesús MJ

Molecules (Basel, Switzerland) 20191121 23

New substituted benzo[g]indazoles functionalized with a 6-nitro and 6-amino groups have been synthesized by the reaction of benzylidene tetralones with hydrazine in acetic acid. The resulting conformationally-constrained compounds were evaluated for their antiproliferative activity against selected cancer cell lines. The nitro-based indazoles 11a, 11b, 12a and 12b have shown IC50 values between 5-15 μM against the lung carcinoma cell line NCI-H460. Moreover ...[more]

PMID: 31766444

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