Preparation and X-Ray Crystal Structure of 3-(4-(Dimethylamino)phenyl)-2-(phenylamino)isoquinolin-1(2H)-one, 3-(4-Methoxyphenyl)-2-(phenylamino)isoquinolin-1(2H)-one, and 2-Methyl-N′-(4-methylbenzoyl)-N′-phenylbenzohydrazide from Polylithiated 2-methylbenzoic Acid Phenylhydrazide and Methyl 4-dimethylaminobenzoate, Methyl 4-methoxybenzoate, or Methyl 4-methylbenzoate

Shuler, William G.; Smith, Ellyn A.; Hess, Sloan M.; McFadden, Thomas M. C.; Metz, Clyde; VanDerveer, Donald G.; Pennington, William T.; Mabe, Phillip J.; Knick, Shabree L.; Beam, Charles F.

doi:10.1007/s10870-012-0342-5

Cited by 3 publications

(1 citation statement)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All synthesised derivatives underwent rigid receptor docking, and their postures were visually analysed. After downloading the X-ray crystal structure of InhA with N-(4-methylbenzoyl)-4-benzylpiperidine, PDB ID: 2NSD (Resolution: 1.90), a protein was made [25]. Enzyme preparation utilised Autodoc 4.2 (adding polar hydrogens, adding AD4 type atoms, removing water molecules, and heteroatoms).…”

Section: Molecular Dockingmentioning

confidence: 99%

Design, Synthesis, Anti-Tubercular Evaluation and Teratogenicity Studies of Furanyl Pyrazolo[3,4-b] Quinoline-5-Ones

et al. 2022

View full text Add to dashboard Cite

We have synthesized novel pyrazolo-quinoline analogues (P1-10) in an effort to create newer antitubercular drugs against the rising bacterial resistance. NMR, IR and ESI-MS spectra were utilized to characterize the synthesised compounds. The antitubercular activity of the target compounds was evaluated against Mycobacterium tuberculosis. Six derivatives (P1-6) displayed very significant activity at 1.6 μg/mL concentration and were found to be more active than pyrazinamide standard. Thus, as per the drug susceptibility results the MIC value could be considered between 1.6 and 0.8 μg/mL. In addition, all the synthesised compounds were subjected to molecular docking studies against specific protein, Enoyl acyl carrier protein reductase (InhA) in complex with N-(4-methylbenzoyl)-4-benzylpiperidine, PDB ID: 2NSD. Among all the compounds the most effective compounds were found an Autodock score of 11.6 and 11.2 against 2NSD, respectively. Further, Zebrafish larvae have been used to test the teratogenicity of the synthesised compounds. There were no indications of abnormalities with (P2), (P4), (P5), (P6), and (P10) at 0.5 μM.

show abstract

Section: Molecular Dockingmentioning

confidence: 99%

Design, Synthesis, Anti-Tubercular Evaluation and Teratogenicity Studies of Furanyl Pyrazolo[3,4-b] Quinoline-5-Ones

et al. 2022

View full text Add to dashboard Cite

show abstract

Rh(iii)-Catalyzed three-component cascade annulation to produce the N-oxopropyl chain of isoquinolone derivatives

Liao

Dong

et al. 2021

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Design, Synthesis, and Biological Evaluation of N′-Phenylhydrazides as Potential Antifungal Agents

Zhu,

Zheng,

Yan

et al. 2023

IJMS

View full text Add to dashboard Cite

Fifty-two kinds of N′-phenylhydrazides were successfully designed and synthesized. Their antifungal activity in vitro against five strains of C. albicans (Candida albicans) was evaluated. All prepared compounds showed varying degrees of antifungal activity against C. albicans and their MIC80 (the concentration of tested compounds when their inhibition rate was at 80%), TAI (total activity index), and TSI (total susceptibility index) were calculated. The inhibitory activities of 27/52 compounds against fluconazole-resistant fungi C. albicans 4395 and 5272 were much better than those of fluconazole. The MIC80 values of 14/52 compounds against fluconazole-resistant fungus C. albicans 5122 were less than 4 μg/mL, so it was the most sensitive fungus (TSIB = 12.0). A11 showed the best inhibitory activity against C. albicans SC5314, 4395, and 5272 (MIC80 = 1.9, 4.0, and 3.7 μg/mL). The antifungal activities of B14 and D5 against four strains of fluconazole-resistant fungi were better than those of fluconazole. The TAI values of A11 (2.71), B14 (2.13), and D5 (2.25) are the highest. Further exploration of antifungal mechanisms revealed that the fungus treated with compound A11 produced free radicals and reactive oxygen species, and their mycelium morphology was damaged. In conclusion, the N′-phenylhydrazide scaffold showed potential in the development of antifungal lead compounds. Among them, A11, B14, and D5 demonstrated particularly promising antifungal activity and held potential as novel antifungal agents.

show abstract

Cited by 3 publications

References 16 publications

Design, Synthesis, Anti-Tubercular Evaluation and Teratogenicity Studies of Furanyl Pyrazolo[3,4-b] Quinoline-5-Ones

Design, Synthesis, Anti-Tubercular Evaluation and Teratogenicity Studies of Furanyl Pyrazolo[3,4-b] Quinoline-5-Ones

Rh(iii)-Catalyzed three-component cascade annulation to produce the N-oxopropyl chain of isoquinolone derivatives

Design, Synthesis, and Biological Evaluation of N′-Phenylhydrazides as Potential Antifungal Agents

Contact Info

Product

Resources

About