Antitubercular and antimicrobial activity of nh4vo3 promoted 1,4-dihydropyridine incorporated 1,3,4-Trisubstituted pyrazole

Nandam Harikrishna, Arun M. Isloor, K. Ananda, Tanya Parish, Joazaizulfazli Jamalis, Hazem A. Ghabbour, Hoong Kun Fun

Research output: Research - peer-reviewArticle

Abstract

Background: A new series of pyrazole containing 1,4-dihydropyridine derivatives 5a-i and 6a-i were synthesized from substituted acetylated aryls and substituted phenylhydrazine by the multistep reaction. Method: The target compounds 1,4-dihydropyridine derivatives were obtained from green synthesis of 1,3-disubstituted phenyl-1H-pyrazole-4-carbaldehydes 4a-i with ethyl acetoacetate and methyl acetoacetate at higher temperatures in the presence of ammonium acetate and the catalytic amount of ammonium metavanadate (NH4VO3). The role of ammonium metavanadate was increases rate of the reaction and obtained high yields. Result: Structures of newly synthesized 1,4-dihydropyridine moiety containing pyrazole derivatives were confirmed by FT-IR, NMR and Mass spectral studies. The structure of compound 5b was confirmed by S-XRD study. Further, these compounds were tested for in-vitro antitubercular and antimicrobial studies. Compounds 5a, 5b, 5i, 6a, 6b, 6g, 6h, and 6i were found to be active against all the bacterial microorganisms. Conclusion: The above mentioned compounds have shown lowest MIC ranging between 3.12-12.5 μg/ml against Mycobacterium tuberculosis and MIC values ranging between 7.8- 15.6 μg/ml for Mycobacterium smegmatis, Staphylococcus aureus and Pseudomonas aeruginosa. For the control of life threatening diseases such as tuberculosis, these eight compounds may be strongly promising synthetic compounds.

LanguageEnglish
Pages699-711
Number of pages13
JournalLetters in Drug Design and Discovery
Volume14
Issue number6
DOIs
StatePublished - 1 Jan 2017

Fingerprint

1,4-dihydropyridine
pyrazole
ammonium metavanadate
Mycobacterium smegmatis
Mycobacterium tuberculosis
Pseudomonas aeruginosa
Staphylococcus aureus
Tuberculosis
phenylhydrazine
In Vitro Techniques
ethyl acetoacetate
ammonium acetate
methyl acetoacetate

Keywords

  • 1 3 4-Trisubstituted pyrazole
  • 1 4-dihydropyridine
  • Ammonium metavanadate
  • Antimicrobial studies
  • Antitubercular study
  • Multistep reaction

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery

Cite this

Antitubercular and antimicrobial activity of nh4vo3 promoted 1,4-dihydropyridine incorporated 1,3,4-Trisubstituted pyrazole. / Harikrishna, Nandam; Isloor, Arun M.; Ananda, K.; Parish, Tanya; Jamalis, Joazaizulfazli; Ghabbour, Hazem A.; Fun, Hoong Kun.

In: Letters in Drug Design and Discovery, Vol. 14, No. 6, 01.01.2017, p. 699-711.

Research output: Research - peer-reviewArticle

Harikrishna, Nandam ; Isloor, Arun M. ; Ananda, K. ; Parish, Tanya ; Jamalis, Joazaizulfazli ; Ghabbour, Hazem A. ; Fun, Hoong Kun. / Antitubercular and antimicrobial activity of nh4vo3 promoted 1,4-dihydropyridine incorporated 1,3,4-Trisubstituted pyrazole. In: Letters in Drug Design and Discovery. 2017 ; Vol. 14, No. 6. pp. 699-711
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abstract = "Background: A new series of pyrazole containing 1,4-dihydropyridine derivatives 5a-i and 6a-i were synthesized from substituted acetylated aryls and substituted phenylhydrazine by the multistep reaction. Method: The target compounds 1,4-dihydropyridine derivatives were obtained from green synthesis of 1,3-disubstituted phenyl-1H-pyrazole-4-carbaldehydes 4a-i with ethyl acetoacetate and methyl acetoacetate at higher temperatures in the presence of ammonium acetate and the catalytic amount of ammonium metavanadate (NH4VO3). The role of ammonium metavanadate was increases rate of the reaction and obtained high yields. Result: Structures of newly synthesized 1,4-dihydropyridine moiety containing pyrazole derivatives were confirmed by FT-IR, NMR and Mass spectral studies. The structure of compound 5b was confirmed by S-XRD study. Further, these compounds were tested for in-vitro antitubercular and antimicrobial studies. Compounds 5a, 5b, 5i, 6a, 6b, 6g, 6h, and 6i were found to be active against all the bacterial microorganisms. Conclusion: The above mentioned compounds have shown lowest MIC ranging between 3.12-12.5 μg/ml against Mycobacterium tuberculosis and MIC values ranging between 7.8- 15.6 μg/ml for Mycobacterium smegmatis, Staphylococcus aureus and Pseudomonas aeruginosa. For the control of life threatening diseases such as tuberculosis, these eight compounds may be strongly promising synthetic compounds.",
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T1 - Antitubercular and antimicrobial activity of nh4vo3 promoted 1,4-dihydropyridine incorporated 1,3,4-Trisubstituted pyrazole

AU - Harikrishna,Nandam

AU - Isloor,Arun M.

AU - Ananda,K.

AU - Parish,Tanya

AU - Jamalis,Joazaizulfazli

AU - Ghabbour,Hazem A.

AU - Fun,Hoong Kun

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Y1 - 2017/1/1

N2 - Background: A new series of pyrazole containing 1,4-dihydropyridine derivatives 5a-i and 6a-i were synthesized from substituted acetylated aryls and substituted phenylhydrazine by the multistep reaction. Method: The target compounds 1,4-dihydropyridine derivatives were obtained from green synthesis of 1,3-disubstituted phenyl-1H-pyrazole-4-carbaldehydes 4a-i with ethyl acetoacetate and methyl acetoacetate at higher temperatures in the presence of ammonium acetate and the catalytic amount of ammonium metavanadate (NH4VO3). The role of ammonium metavanadate was increases rate of the reaction and obtained high yields. Result: Structures of newly synthesized 1,4-dihydropyridine moiety containing pyrazole derivatives were confirmed by FT-IR, NMR and Mass spectral studies. The structure of compound 5b was confirmed by S-XRD study. Further, these compounds were tested for in-vitro antitubercular and antimicrobial studies. Compounds 5a, 5b, 5i, 6a, 6b, 6g, 6h, and 6i were found to be active against all the bacterial microorganisms. Conclusion: The above mentioned compounds have shown lowest MIC ranging between 3.12-12.5 μg/ml against Mycobacterium tuberculosis and MIC values ranging between 7.8- 15.6 μg/ml for Mycobacterium smegmatis, Staphylococcus aureus and Pseudomonas aeruginosa. For the control of life threatening diseases such as tuberculosis, these eight compounds may be strongly promising synthetic compounds.

AB - Background: A new series of pyrazole containing 1,4-dihydropyridine derivatives 5a-i and 6a-i were synthesized from substituted acetylated aryls and substituted phenylhydrazine by the multistep reaction. Method: The target compounds 1,4-dihydropyridine derivatives were obtained from green synthesis of 1,3-disubstituted phenyl-1H-pyrazole-4-carbaldehydes 4a-i with ethyl acetoacetate and methyl acetoacetate at higher temperatures in the presence of ammonium acetate and the catalytic amount of ammonium metavanadate (NH4VO3). The role of ammonium metavanadate was increases rate of the reaction and obtained high yields. Result: Structures of newly synthesized 1,4-dihydropyridine moiety containing pyrazole derivatives were confirmed by FT-IR, NMR and Mass spectral studies. The structure of compound 5b was confirmed by S-XRD study. Further, these compounds were tested for in-vitro antitubercular and antimicrobial studies. Compounds 5a, 5b, 5i, 6a, 6b, 6g, 6h, and 6i were found to be active against all the bacterial microorganisms. Conclusion: The above mentioned compounds have shown lowest MIC ranging between 3.12-12.5 μg/ml against Mycobacterium tuberculosis and MIC values ranging between 7.8- 15.6 μg/ml for Mycobacterium smegmatis, Staphylococcus aureus and Pseudomonas aeruginosa. For the control of life threatening diseases such as tuberculosis, these eight compounds may be strongly promising synthetic compounds.

KW - 1 3 4-Trisubstituted pyrazole

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KW - Ammonium metavanadate

KW - Antimicrobial studies

KW - Antitubercular study

KW - Multistep reaction

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SN - 1570-1808

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