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Antimicrobial screening and one-pot synthesis of 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives.

Goel N, Drabu S, Afzal O, Bawa S - J Pharm Bioallied Sci (2014)

Bottom Line: A series of compounds (4a-4k) was synthesized through direct reductive amination of 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with various substituted aromatic amines using NaBH4 in the presence of I2 as reducing agent.Most of the compounds exhibited considerable antifungal activity, but poor antibacterial activity against the test strains.In the series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain Aspergillus niger (MTCC) 281 and Aspergillus flavus MTCC 277 (% inhibition in the range of 47.7-58.9).

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, Maharaja Surajmal Institute of Pharmacy, (Affiliated to GGSIP University), Janakpuri, New Delhi, India.

ABSTRACT

Aim: Synthesis of series of 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a-4k) and their in vitro antifungal and antibacterial screening.

Materials and methods: A series of compounds (4a-4k) was synthesized through direct reductive amination of 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with various substituted aromatic amines using NaBH4 in the presence of I2 as reducing agent. The reaction was carried out in anhydrous methanol under neutral conditions at room temperature. The structures of synthesized compounds (4a-4k) were established on the basis of IR, (1)H and (13)C-NMR, and mass spectral data.

Results: All 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a-4k) were tested in vitro for antifungal and antibacterial activities against different fungal and bacterial strains. Most of the compounds exhibited considerable antifungal activity, but poor antibacterial activity against the test strains.

Conclusion: In the series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain Aspergillus niger (MTCC) 281 and Aspergillus flavus MTCC 277 (% inhibition in the range of 47.7-58.9).

No MeSH data available.


Related in: MedlinePlus

Bar diagram showing antifungal activity of compounds (4a–4k) against fungal strain Candida albicans, Aspergillus niger and Aspergillus flavus
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Figure 3: Bar diagram showing antifungal activity of compounds (4a–4k) against fungal strain Candida albicans, Aspergillus niger and Aspergillus flavus

Mentions: All the 1H-pyrazolyl amines derivatives (4a–4k) of Scheme 1 displayed variable growth inhibitory effects against the test organism at concentration of 500 μg/ml in DMSO as shown in Table 1 and Figure 3. Among the series of compounds (4a–4k), compounds 4b, 4d, 4e, and 4g showed good antifungal activity against C. albicans. The growth inhibitory effect of compounds (4a–4k) was more prominent against the fungal strain A. niger MTCC 281 and A. flavus MTCC 277. In this series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain A. niger MTCC 281 and A. flavus MTCC 277 (% inhibition in the range of 47.7–58.9). While, rest of the compounds such as 4a, 4c, 4d, 4f, and 4i, displayed moderate antifungal activity. Only one derivative 4h expressed weak antifungal activity.


Antimicrobial screening and one-pot synthesis of 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives.

Goel N, Drabu S, Afzal O, Bawa S - J Pharm Bioallied Sci (2014)

Bar diagram showing antifungal activity of compounds (4a–4k) against fungal strain Candida albicans, Aspergillus niger and Aspergillus flavus
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4231385&req=5

Figure 3: Bar diagram showing antifungal activity of compounds (4a–4k) against fungal strain Candida albicans, Aspergillus niger and Aspergillus flavus
Mentions: All the 1H-pyrazolyl amines derivatives (4a–4k) of Scheme 1 displayed variable growth inhibitory effects against the test organism at concentration of 500 μg/ml in DMSO as shown in Table 1 and Figure 3. Among the series of compounds (4a–4k), compounds 4b, 4d, 4e, and 4g showed good antifungal activity against C. albicans. The growth inhibitory effect of compounds (4a–4k) was more prominent against the fungal strain A. niger MTCC 281 and A. flavus MTCC 277. In this series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain A. niger MTCC 281 and A. flavus MTCC 277 (% inhibition in the range of 47.7–58.9). While, rest of the compounds such as 4a, 4c, 4d, 4f, and 4i, displayed moderate antifungal activity. Only one derivative 4h expressed weak antifungal activity.

Bottom Line: A series of compounds (4a-4k) was synthesized through direct reductive amination of 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with various substituted aromatic amines using NaBH4 in the presence of I2 as reducing agent.Most of the compounds exhibited considerable antifungal activity, but poor antibacterial activity against the test strains.In the series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain Aspergillus niger (MTCC) 281 and Aspergillus flavus MTCC 277 (% inhibition in the range of 47.7-58.9).

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmaceutical Chemistry, Maharaja Surajmal Institute of Pharmacy, (Affiliated to GGSIP University), Janakpuri, New Delhi, India.

ABSTRACT

Aim: Synthesis of series of 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a-4k) and their in vitro antifungal and antibacterial screening.

Materials and methods: A series of compounds (4a-4k) was synthesized through direct reductive amination of 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with various substituted aromatic amines using NaBH4 in the presence of I2 as reducing agent. The reaction was carried out in anhydrous methanol under neutral conditions at room temperature. The structures of synthesized compounds (4a-4k) were established on the basis of IR, (1)H and (13)C-NMR, and mass spectral data.

Results: All 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a-4k) were tested in vitro for antifungal and antibacterial activities against different fungal and bacterial strains. Most of the compounds exhibited considerable antifungal activity, but poor antibacterial activity against the test strains.

Conclusion: In the series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain Aspergillus niger (MTCC) 281 and Aspergillus flavus MTCC 277 (% inhibition in the range of 47.7-58.9).

No MeSH data available.


Related in: MedlinePlus