Synthesis, anti-tuberculosis activity, and 3D-QSAR study of 4-(adamantan-1-yl)-2-substituted quinolines

Nayyar, Amit; Monga, Vikramdeep; Malde, Alpeshkumar K.; Coutinho, Evans C.; Jain, Rahul

doi:10.1016/j.bmc.2006.10.064

Cited by 133 publications

(64 citation statements)

References 19 publications

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“…The presence of two singlet peaks for NH and NH 2 at δ 3.88 ppm and δ 7.49 ppm, respectively, revealed the formation of undec-10-ene hydrazide 3. The appearance of singlet signal ranging from δ 7.49 to 10.72 ppm in the synthesized compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) confirmed the presence of NH of hydrazide derivatives. The appearance of singlet signal of CH proton in compounds 5 at δ 7.92 ppm revealed the formation of N=CH bond in the synthesized derivative.…”

Section: Kumari Et Almentioning

confidence: 77%

“…The synthesis of the intermediate (2,3) and target compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) was performed according to reactions outlined in Schemes 1 and 2. A methanolic solution of undecylenic acid 1 was refluxed in the presence of sulfuric acid to yield the methyl ester undecylenic acid (2).…”

Section: Spectral Data Analysismentioning

confidence: 99%

“…The methyl ester 2 was refluxed with hydrazine hydrate to yield undec-10-ene hydrazide 3, which was condensed with corresponding aromatic aldehydes/acetophenone to synthesize the target undec-10-ene hydrazide derivatives (4-13). Then, corresponding undec-10-enehydrazide derivatives (4-6) was refluxed with chloroacetyl chloride and triethylamine in dioxane to produce azetidinone derivatives (14)(15)(16). The undec-10-ene hydrazide 3 was also reacted with ethyl acetoacetate; acetic acid in acetic anhydride and acetic anhydride to yield…”

Section: Spectral Data Analysismentioning

confidence: 99%

“…Further, the previous studies performed by us revealed the significance of different acid derivatives, including undec-10-enoic hydrazide-hydrazone derivatives as antibacterial and antifungal agents [6][7][8][9][10][11]. Studies reported by various research groups also showed that hydrazide-hydrazone derivatives of different acids have wide range of biological activities, viz., antibacterial [12], antifungal [13], antitubercular [14], trypnocidal [15], antimalarial [16], antiviral [8], anti-inflammatory [17], and antitumor [18] activities. Isoniazid (antitubercular) [19], nifuroxazide (antidiarrheal and antitumor) [20], nifurtimox (antiamoebic) [21], furacin (antibiotic) [22], and furazolidone (antibacterial) [23] are hydrazide containing important biologically active drug molecules.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

Kumari

Narang

Nayak

et al. 2017

Asian J Pharm Clin Res

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Objective: In recent years, an increasing frequency and severity of antimicrobial resistance to different antimicrobial agents, demands new remedies for the treatment of infections. Therefore, in this study, a series of undec-10-enehydrazide derivatives were synthesized and screened for in vitro activity against selected pathogenic microbial strains. Methods:The synthesis of the intermediate and target compounds was performed by standard procedure. Synthesized compounds were screened for antimicrobial activity by tube dilution method. Molecular docking study of synthesized derivatives was also performed to find out their interaction with the target site of β-ketoacyl-acyl carrier protein synthase III, (FabH; pdb id:3IL7) by docking technique. Quantitative structure-activity relationship (QSAR) studies were also performed to correlate antimicrobial activity with structural properties of synthesized molecules.Results: Antimicrobial screening results showed that compound 8 having benzylidine moiety with methoxy groups at meta and para position and compound 16 having 3-chloro-2-(3-flourophenyl)-4-oxoazetidine moiety was found to be most potent. QSAR studies revealed the importance of Randic topology parameter (R) in describing the antimicrobial activity of synthesized derivatives. Molecular docking study indicated hydrophobic interaction of deeply inserted aliphatic side chain of the ligand with FabH. The N-atoms of hydrazide moiety interacts with Ala246 and Asn247 through H-bonding. The m-and p-methoxy groups form H-bond with water and side chain of Arg36, respectively. Conclusion:Compound 8 having benzylidine moiety with methoxy groups at meta and para position and compound 16 having 3-chloro-2-(3-flourophenyl)-4-oxoazetidine moiety was found to most potent antibacterial and antifungal compounds, respectively.

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Section: Kumari Et Almentioning

confidence: 77%

Section: Spectral Data Analysismentioning

confidence: 99%

Section: Spectral Data Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

Kumari

Narang

Nayak

et al. 2017

Asian J Pharm Clin Res

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“…3D-QSAR analysis has been employed by Rahul Jain and co-worker to understand the relationship between structure and anti-TB activity. They develop new 4-(adamantan-1-yl)-2-substituted quinolines derivatives, the most potent analog of the series produces 99% inhibition at 1.00 μg/mL against drug-sensitive strain, and MIC of 3.125 μg/mL against isoniazid resistant TB strain [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Mannich Products Bearing Quinoline Nucleous Using Reusable Ionic Liquid and Antitubercular Evaluation

Patel¹

2015

GSC

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A series of Mannich products bearing quinoline nucleus was synthesized, characterized, and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H 37 Rv. The results showed that compounds 4b, and 4d found most active with percentage inhibition of 95, and 96, respectively, at minimum inhibitory concentration (MIC) of >6.25 µg/mL, among the synthesized compounds. Whereas, compounds 4a, 4c, 4e, and 4f exhibited considerable antitubercular activity with percentage inhibition of 71, 79, 55, and 68, respectively, at MIC of >6.25 µg/mL. The structures of synthesized compounds were elucidated by various spectroscopic tools like IR, 1 H NMR, 13 C NMR, mass and elemental analysis.

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Visible‐light‐induced Reactions Driven by Photochemical Activity of Quinolinone and Coumarin Scaffolds

Vellakkaran

Hong

2021

Asian J Org Chem

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Organic photocatalysis has garnered significant interest in the field of photochemistry because of its ability to generate active radical species under mild conditions via energy or electron transfer from the excited state of photosensitizers to organic molecules. Quinolinones and coumarins are privileged scaffolds that are widely distributed in natural products and pharmaceutical agents. Recently, quinolinones and coumarins have emerged as promising organic photo-sensitizers for a variety of chemical transformations. Significant advances in the development of synthetic methods via organic photocatalysis have elucidated their essential electronic properties, leading to the development of highly siteselective synthetic methods. This mini-review highlights recent innovative approaches to site-selective CÀ H bond functionalization catalyzed by light-absorbing quinolinone and coumarin scaffolds.

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Synthesis, anti-tuberculosis activity, and 3D-QSAR study of 4-(adamantan-1-yl)-2-substituted quinolines

Cited by 133 publications

References 19 publications

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

Synthesis, Molecular Modeling, and Quantitative Structure–activity Relationship Studies of Undec-10-Enehydrazide Derivatives as Antimicrobial Agents

Synthesis of New Mannich Products Bearing Quinoline Nucleous Using Reusable Ionic Liquid and Antitubercular Evaluation

Visible‐light‐induced Reactions Driven by Photochemical Activity of Quinolinone and Coumarin Scaffolds

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