Design, diversity-oriented synthesis and structure activity relationship studies of quinolinyl heterocycles as antimycobacterial agents

Rachakonda, Venkatesham; Manjula, A.; Kotipalli, Sudha Sravanti; Ummani, Ramesh

doi:10.1016/j.ejmech.2013.10.034

Cited by 33 publications

(19 citation statements)

References 28 publications

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“…According to the research by Encinas et al, benzofuran pyrazole derivatives showed considerable in vitro activity against MTB H37Rv, and compound 385 showed the most potency with MIC 90 of 0.05 µM [ 284 ]. A series of quinolinyl heterocycles were evaluated for their anti-mycobacterial activity against M. smegmatis , and some quinolinyl pyrazole hybrids showed excellent anti-mycobacterial activity such as 386 (MIC = 14.66 µg/mL) was as potent as isoniazide (MIC = 12.07 µg/mL) [ 285 ].The in vitro abilities of quinazolinone pyrazole derivatives to inhibit growth of MTB H37Rv have been reported by Pandit et al The results exhibited all hybrids showed considerable anti-TB activity, particularly, hybrid 387 (96%, MIC 90 < 3.125 µg/mL) warrant further investigation [ 286 ]. Dihydropyrimidine pyrazole derivatives were synthesized and evaluated for their in vitro anti-tubercular activity against MTB H37Rv, compound 388 were found to be the most active compounds in vitro with MIC of 0.02 µg/mL, with the highest SI > 500 were more potent than INH (0.03 µg/mL) [ 287 ].…”

Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antipsychotic CDPPB, the anti-obesity drug rimonabant, difenamizole, an analgesic, betazole, a H2-receptor agonist and the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. This review highlights the different synthesis methods and the pharmacological properties of pyrazole derivatives. Studies on the synthesis and biological activity of pyrazole derivatives developed by many scientists around the globe are reported.

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Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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“…[1][2][3][4][5][6][7] The production of these libraries allows for the analysis of structure-activity relationships of the compounds, which helps inform further development of probes with diverse activity. [8][9][10][11][12][13][14][15][16] Biological performance diversity can be defined as the ability of a compound library to target a broad variety of biological functions, while containing few molecules with redundant activity. Such libraries more efficiently use resources, due to a smaller library footprint, while potentially increasing hit rates.…”

Section: Introductionmentioning

confidence: 99%

Multiple Chemical Features Impact Biological Performance Diversity of a Highly Active Natural Product‐Inspired Library

et al. 2020

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A systematic, diversity-oriented synthesis approach was employed to access a natural product-inspired flavonoid library with diverse chemical features, including chemical properties, scaffold, stereochemistry, and appendages. Using Cell Painting, the effects of these diversity elements were evaluated, and multiple chemical features that predict biological performance diversity were identified. Scaffold identity appears to be the dominant predictor of performance diversity, but stereochemis-try and appendages also contribute to a lesser degree. In addition, the diversity of chemical properties contributed to performance diversity, and the driving chemical property was dependent on the scaffold. These results highlight the importance of key chemical features that may inform the creation of small-molecule, performance-diverse libraries to improve the efficiency and success of high-throughput screening campaigns.

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“…Different coupling reagents are used for the final cyclization including DIC, DCC as carbodiimides, TBTU as uronium coupling reagent 46 . Considering these characteristics, IBD is one of the common coupling reagents and additives used in cyclization chemistry [47][48][49][50] . Considering these characteristics, IBD is one of the common coupling reagents and additives used in cyclization chemistry [47][48][49][50] .…”

Section: Cytotoxicity (Brine Shrimp Lethality Bioassay)mentioning

confidence: 99%

Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities

Ladani

Patel

2015

New J. Chem.

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A series of quinoline based 1,3,4-oxadiazole derivatives 8a-l were synthesized by chloro-amine coupling reaction approach with different catalyst and solvents. The substituted 1,3,4-oxadiazole intermediates 7a-c were obtained from 2-sustituted-N-phenylhydrazinecarbothioamide 6a-c by cyclization with different cyclizing reagents like mercuric acetate, lead dioxide, iodobenzenediacetate (IBD) and aqueous sodium hydroxide with iodine in aqueous potassium iodide to isolate the most effective reaction condition by using iodobenzenediacetate as extremely good catalyst. The structure of the title compounds were confirmed by FT-IR, 1 H NMR, 13 C NMR and mass spectrometry. The synthesized molecules were evaluated for their antibacterial, antifungal, antituberculosis and antimalarial activities. The brine shrimp bioassay was carried out to study the in vitro cytotoxic properties for the highly active compounds of in vitro biological evaluation. antifungal 34 . Quinoline scaffolds have been selected due to their diverse therapeutic and pharmacological properties, such as antitumor, antiatherosclerotic, vasodilator, geroprotective, bronchodilator and hepatoprotective activity 35 .

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Design, diversity-oriented synthesis and structure activity relationship studies of quinolinyl heterocycles as antimycobacterial agents

Cited by 33 publications

References 28 publications

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Multiple Chemical Features Impact Biological Performance Diversity of a Highly Active Natural Product‐Inspired Library

Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities

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