A convenient synthesis and screening of benzosuberone bearing 1,2,3-triazoles against Mycobacterium tuberculosis

Sajja, Yasodakrishna; Vanguru, Sowmya; Jilla, Lavanya; Vulupala, Hanmanth Reddy; Bantu, Rajashaker; Yogeswari, Perumal; Sriram, Dharmarajan; Nagarapu, Lingaiah

doi:10.1016/j.bmcl.2016.07.039

Cited by 29 publications

(10 citation statements)

References 34 publications

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“…Appropriate names (if possible) for all the new compounds were given with the help of ChemBioOffice v12.0; 2012. The starting compound ( 1 ) (2,3‐dimethyl‐6,7,8,9‐tetrahydro‐5 H ‐benzo[7]annulen‐5‐one) and compound ( 2 ) (( Z )‐9‐chloro‐2,3‐dimethyl‐6,7‐dihydro‐5 H ‐benzo[7]annulene‐8‐carbaldehyde) were prepared according to a previously reported procedure …”

Section: Methodsmentioning

confidence: 99%

“…However, this anticancer drug has not reached clinical applications due to its high toxicity although it currently finds use in medical therapy for gout, acute pericarditis, and familial Mediterranean fever . Nevertheless, its derivatives exhibit a wide range of biological activities including antimicrobial (Compounds I, II, and III) (Figure ), antipyretic, antiulcer, antitubercular, anticonvulsant activities, and antidepressants, like amitriptyline and imipramine, used as first line drugs.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of novel piperazine tethered benzocycloheptenone hybrids and their antimicrobial evaluation

Prameela

Jilla

Vanguru

2019

Journal of Heterocyclic Chem

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A new series of benzosuberone-piperazine hybrids 6a to j were designed and synthesized efficiently in good yields and their structures were confirmed by 1 H NMR, 13 C NMR, ESI-MS and HRMS. The newly synthesized compounds were evaluated for their in vitro antimicrobial activity against Gram positive, Gram negative bacterial strains and a fungal strain. Among the synthesized compounds, compounds 6c, 6d, 6e, 6f, 6g and 6h exhibited potent antibacterial activity with MIC value of 1.9 μg/mL against Gram positive and Gram negative organisms.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of novel piperazine tethered benzocycloheptenone hybrids and their antimicrobial evaluation

Prameela

Jilla

Vanguru

2019

Journal of Heterocyclic Chem

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“…In an effort to prepare better therapeutic agents for the treatment of tuberculosis and in continuation to our previous work herein, we have rationally designed and synthesized three biologically versatile heterocyclic scaffolds like benzocycloheptenone, pyridine, and 1,3,4‐oxadiazole in a single molecular platform (Figure ). To establish structure activity relationship and for the development of new antitubercular agents, the final compounds were screened for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv.…”

Section: Introductionmentioning

confidence: 93%

Design, synthesis, and in vitro antituberculosis activity of benzo[6,7]cyclohepta[1,2‐b]pyridine‐1,3,4‐oxadiazole derivatives

et al. 2017

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A new antitubercular agents, benzo[6,7]cyclohepta[1,2-b]pyridine-1,3,4- oxadiazole hybrids (6a-o), have been designed and synthesized involving oxidative cyclization of hydrazones by use of di(acetoxy)iodobenzene, characterized by IR, H NMR, C NMR, and HRMS, and further confirmed by X-ray analysis. All the newly synthesized compounds 4a-o evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (ATCC27294). Among the compounds tested, the compounds 4o (MIC: 1.56 μg/ml) and 4l, 4m (MIC: 3.125 μg/ml) are promising lead analogues and have shown lower cytotoxicity.

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“…Among the several classes of heterocyclic, the 1,2,3-triazoles have received considerable attention from research groups. These five-membered scaffolds are exclusively synthetic in nature, and present a vast array of biological activities, including antibacterial, [4][5][6][7] antifungal, 8 cytotoxic, 9,10 antiviral, 11,12 antimalaric, 13,14 leishmanicidal, 15 anticancerous, 16,17 phytotoxic effects, 18 among others. 19,20 In addition, the monocyclic 1,2,3-triazoles and benzotriazoles present stability towards hydrolysis, oxidative/reductive conditions, and enzymatic degradation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Glycerol-Derived 4-Alkyl-Substituted 1,2,3-Triazoles and Evaluation of Their Fungicidal, Phytotoxic, and Antiproliferative Activities

Costa¹,

Moreira²,

Pinto³

et al. 2020

J. Braz. Chem. Soc.

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Herein, the synthesis of nine novel glycerol-derived 4-alkyl-substituted 1,2,3-triazoles, using the Cu I-catalyzed alkyne-azide cycloaddition reaction as the key step, is reported. The triazoles were characterized by infrared and nuclear magnetic resonance (NMR 1 H and 13 C) spectroscopy and mass spectrometry. The nine prepared compounds were evaluated with regard to their phytotoxic, antiproliferative, and fungicidal activities. The fungicidal activity was assessed on Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. All compounds presented high efficiency (comparable to the commercial fungicide tebuconazole) in inhibiting C. gloeosporioides sporulation. The phytotoxicity of the triazoles was assessed against Lactuca sativa. Germination was the less-affected parameter, whereas the most pronounced effects of the triazoles were on the germination speed index and root growth of the L. sativa seedlings. As indicators of antiproliferative activity, the mitotic index was evaluated along with chromosomal and nuclear alterations, all of which were influenced to different degrees by the triazoles. In addition, all derivatives demonstrated aneugenic and clastogenic actions in meristematic cells of L. sativa roots. Therefore, these 4-alkyl-substituted triazoles may represent a scaffold to be explored for the development of new fungicidal agents.

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A convenient synthesis and screening of benzosuberone bearing 1,2,3-triazoles against Mycobacterium tuberculosis

Cited by 29 publications

References 34 publications

Synthesis of novel piperazine tethered benzocycloheptenone hybrids and their antimicrobial evaluation

Synthesis of novel piperazine tethered benzocycloheptenone hybrids and their antimicrobial evaluation

Design, synthesis, and in vitro antituberculosis activity of benzo[6,7]cyclohepta[1,2‐b]pyridine‐1,3,4‐oxadiazole derivatives

Synthesis of Glycerol-Derived 4-Alkyl-Substituted 1,2,3-Triazoles and Evaluation of Their Fungicidal, Phytotoxic, and Antiproliferative Activities

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