Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives

Hussniya al Difar

Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives

Hussniya al Difar | International Journal of Chemical Synthesis and Chemical Reactions | Vol 10, Issue 01 | pp. 26-36 | ISSN: 2582-5917

Abstract

In a successful trial to synthesize pyrazole derivatives, acetophenone was, first, reacted with phenylhydrazine producing the Schiffs’s base condensation product (E)-1-phenyl-2-(2-phenylethylidene) hydrazine 1. The application of Vilsmeier Haack’s reaction on this product afforded the cyclization product (1,3-diphenyl-1H-pyrazole-4-carbaldehyde 2 as a pyrazole derivative in good yield percentage. The treatment of (1,3-diphenyl-1H-pyrazole-4-carbaldehyde (2) with acetophenone results in the formation of another pyrazole derivative (3),having a chalcone moiety.The chemical structure of newly formed pyrazole derivatives was confirmed based on spectral data, and these compounds were screened for their anti-bacterial activity. Further exploration of the synthetic potential of compound (2) involved its reaction with acetophenone, resulting in the formation of another pyrazole derivative (3) incorporating a chalcone moiety. This newly formed compound exhibited a distinct structural characteristic, distinguished by the presence of a chalcone unit. Comprehensive spectral analysis was employed to elucidate the chemical structures of these newly synthesized pyrazole derivatives. Furthermore, these compounds were evaluated for their potential antibacterial activities. The results obtained from this screening process shed light on the antibacterial efficacy of these pyrazole derivatives, offering valuable insights into their potential applications in the field of medicinal chemistry. To assess their potential applications, these pyrazole derivatives were evaluated for their antibacterial activities. The screening results provided valuable insights into their efficacy against various bacterial strains, highlighting their potential as promising candidates for further investigation in the field of medicinal chemistry.

Keywords

Vilsmeier Haack reagent, chalcone, condensation, bipyrazole, Acetophenone

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References

Alam R, Wahi D, Singh R, Sinha D, Tandon V, Grover A. Design, synthesis, cytotoxicity, HuTopoIIα inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents. Bioorg Chem. 2016;69:77–90.
Gregory WA, Brittelli DR, Wang CL, Wuonola MA, McRipley RJ, Eustice DC, Eberly VS, Slee AM, Forbes M, Bartholomew PT. Antibacterials. Synthesis and structure–activity studies of 3-aryl-2-oxooxazolidines. 1. The B group. J Med Chem. 1989;32(8):1673–1681.
Ferreira SB, Sodero AC, Cardoso MF, Lima ES, Kaiser CR, Silva FP Jr, Ferreira VF. Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as α-glucosidase inhibitors. J Med Chem. 2010;53(6):2364–2375.
Alam MA. Antibacterial pyrazoles: Tackling resistant bacteria. Future Med Chem. 2022;14(5):343–362.
Gao M, Qu K, Zhang W, Wang X. Pharmacological activity of pyrazole derivatives as an anticonvulsant for benefit against epilepsy. Neuroimmunomodulation. 2021;28(2):90–98.
Kenchappa R, Bodke YD. Synthesis, analgesic and anti-inflammatory activity of benzofuran–pyrazole heterocycles. Chem Data Collect. 2020;28:100453.
Kumar RS, Arif IA, Ahamed A, Idhayadhulla A. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J Biol Sci. 2016;23(5):614–620.
Naim MJ, Alam O, Alam MJ, Shaquiquzzaman M, Alam MM, Naidu VG. Synthesis, docking, in vitro and in vivo antidiabetic activity of pyrazole-based 2,4-thiazolidinedione derivatives as PPAR-γ modulators. Arch Pharm (Weinheim). 2018;351(3–4):e1700223.
Li G, Cheng Y, Han C, Song C, Huang N, Du Y. Pyrazole-containing pharmaceuticals: target, pharmacological activity, and their SAR studies. RSC Med Chem. 2022;13(11):1300–1321.
Bennani FE, Doudach L, Cherrah Y, Ramli Y, Karrouchi K, Faouzi ME. Overview of recent developments of pyrazole derivatives as anticancer agents in different cell lines. Bioorg Chem. 2020;97:103470.
Xu Z, Gao C, Ren QC, Song XF, Feng LS, Lv ZS. Recent advances of pyrazole-containing derivatives as anti-tubercular agents. Eur J Med Chem. 2017;139:429–440.
Naim MJ, Alam O, Nawaz F, Alam MJ, Alam P. Current status of pyrazole and its biological activities. J Pharm Bioallied Sci. 2016;8(1):2–17.
Meth-Cohn O, Stanforth SP. The Vilsmeier–Haack reaction. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon; 1991. p. 777–794.
Okhifo A, Ndukwe GI, Jack IR, Abayeh OJ. Synthesis and antimicrobial evaluation of some simple phenylhydrazones. J Chem Soc Nigeria. 2019;44(2):332–340.
Kumar A, Prakash O, Kinger M, Singh SP. Synthesis of some new 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the Vilsmeier–Haack reaction: isolation of the key intermediate 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles. Can J Chem. 2006;84:438–442.

How to cite this article

APA

Difar, H. A. (2024). Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives. International Journal of Chemical Synthesis and Chemical Reactions, 10(01), 26-36.

MLA

Difar, Hussniya al. “Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives.” International Journal of Chemical Synthesis and Chemical Reactions, vol. 10, no. 01, 2024, pp. 26-36.

Chicago

Hussniya al Difar. “Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives.” International Journal of Chemical Synthesis and Chemical Reactions 10, no. 01 (2024): 26-36.

Vancouver

Difar HA. Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives. International Journal of Chemical Synthesis and Chemical Reactions. 2024;10(01):26-36.

BibTeX

@article{DifarHA2024,
author = {Hussniya al Difar},
title = {Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives},
journal = {International Journal of Chemical Synthesis and Chemical Reactions},
year = {2024},
volume = {10},
number = {01},
pages = {26--36},
issn = {2582-5917},
url = {https://journalspub.com/publication/uncategorized/article=10605}
}

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Hussniya al Difar | International Journal of Chemical Synthesis and Chemical Reactions | Vol 10, Issue 01 | pp. 26-36 | ISSN: 2582-5917

Abstract

Keywords

Vilsmeier Haack reagent, chalcone, condensation, bipyrazole, Acetophenone

🔒 This is a subscription article

Full text is available to subscribers and institutional members. Please choose an option below to access it.

Subscribe Purchase this article Institutional / Login access

References

Alam R, Wahi D, Singh R, Sinha D, Tandon V, Grover A. Design, synthesis, cytotoxicity, HuTopoIIα inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents. Bioorg Chem. 2016;69:77–90.
Gregory WA, Brittelli DR, Wang CL, Wuonola MA, McRipley RJ, Eustice DC, Eberly VS, Slee AM, Forbes M, Bartholomew PT. Antibacterials. Synthesis and structure–activity studies of 3-aryl-2-oxooxazolidines. 1. The B group. J Med Chem. 1989;32(8):1673–1681.
Ferreira SB, Sodero AC, Cardoso MF, Lima ES, Kaiser CR, Silva FP Jr, Ferreira VF. Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as α-glucosidase inhibitors. J Med Chem. 2010;53(6):2364–2375.
Alam MA. Antibacterial pyrazoles: Tackling resistant bacteria. Future Med Chem. 2022;14(5):343–362.
Gao M, Qu K, Zhang W, Wang X. Pharmacological activity of pyrazole derivatives as an anticonvulsant for benefit against epilepsy. Neuroimmunomodulation. 2021;28(2):90–98.
Kenchappa R, Bodke YD. Synthesis, analgesic and anti-inflammatory activity of benzofuran–pyrazole heterocycles. Chem Data Collect. 2020;28:100453.
Kumar RS, Arif IA, Ahamed A, Idhayadhulla A. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J Biol Sci. 2016;23(5):614–620.
Naim MJ, Alam O, Alam MJ, Shaquiquzzaman M, Alam MM, Naidu VG. Synthesis, docking, in vitro and in vivo antidiabetic activity of pyrazole-based 2,4-thiazolidinedione derivatives as PPAR-γ modulators. Arch Pharm (Weinheim). 2018;351(3–4):e1700223.
Li G, Cheng Y, Han C, Song C, Huang N, Du Y. Pyrazole-containing pharmaceuticals: target, pharmacological activity, and their SAR studies. RSC Med Chem. 2022;13(11):1300–1321.
Bennani FE, Doudach L, Cherrah Y, Ramli Y, Karrouchi K, Faouzi ME. Overview of recent developments of pyrazole derivatives as anticancer agents in different cell lines. Bioorg Chem. 2020;97:103470.
Xu Z, Gao C, Ren QC, Song XF, Feng LS, Lv ZS. Recent advances of pyrazole-containing derivatives as anti-tubercular agents. Eur J Med Chem. 2017;139:429–440.
Naim MJ, Alam O, Nawaz F, Alam MJ, Alam P. Current status of pyrazole and its biological activities. J Pharm Bioallied Sci. 2016;8(1):2–17.
Meth-Cohn O, Stanforth SP. The Vilsmeier–Haack reaction. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon; 1991. p. 777–794.
Okhifo A, Ndukwe GI, Jack IR, Abayeh OJ. Synthesis and antimicrobial evaluation of some simple phenylhydrazones. J Chem Soc Nigeria. 2019;44(2):332–340.
Kumar A, Prakash O, Kinger M, Singh SP. Synthesis of some new 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the Vilsmeier–Haack reaction: isolation of the key intermediate 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles. Can J Chem. 2006;84:438–442.

How to cite this article

APA

MLA

Chicago

Vancouver

BibTeX

@article{DifarHA2024,
author = {Hussniya al Difar},
title = {Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives},
journal = {International Journal of Chemical Synthesis and Chemical Reactions},
year = {2024},
volume = {10},
number = {01},
pages = {26--36},
issn = {2582-5917},
url = {https://journalspub.com/publication/uncategorized/article=10605}
}

Hussniya al Difar | International Journal of Chemical Synthesis and Chemical Reactions | Vol 10, Issue 01 | pp. 26-36 | ISSN: 2582-5917

Abstract

Keywords

Vilsmeier Haack reagent, chalcone, condensation, bipyrazole, Acetophenone

🔒 This is a subscription article

Full text is available to subscribers and institutional members. Please choose an option below to access it.

Subscribe Purchase this article Institutional / Login access

References

Alam R, Wahi D, Singh R, Sinha D, Tandon V, Grover A. Design, synthesis, cytotoxicity, HuTopoIIα inhibitory activity and molecular docking studies of pyrazole derivatives as potential anticancer agents. Bioorg Chem. 2016;69:77–90.
Gregory WA, Brittelli DR, Wang CL, Wuonola MA, McRipley RJ, Eustice DC, Eberly VS, Slee AM, Forbes M, Bartholomew PT. Antibacterials. Synthesis and structure–activity studies of 3-aryl-2-oxooxazolidines. 1. The B group. J Med Chem. 1989;32(8):1673–1681.
Ferreira SB, Sodero AC, Cardoso MF, Lima ES, Kaiser CR, Silva FP Jr, Ferreira VF. Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as α-glucosidase inhibitors. J Med Chem. 2010;53(6):2364–2375.
Alam MA. Antibacterial pyrazoles: Tackling resistant bacteria. Future Med Chem. 2022;14(5):343–362.
Gao M, Qu K, Zhang W, Wang X. Pharmacological activity of pyrazole derivatives as an anticonvulsant for benefit against epilepsy. Neuroimmunomodulation. 2021;28(2):90–98.
Kenchappa R, Bodke YD. Synthesis, analgesic and anti-inflammatory activity of benzofuran–pyrazole heterocycles. Chem Data Collect. 2020;28:100453.
Kumar RS, Arif IA, Ahamed A, Idhayadhulla A. Anti-inflammatory and antimicrobial activities of novel pyrazole analogues. Saudi J Biol Sci. 2016;23(5):614–620.
Naim MJ, Alam O, Alam MJ, Shaquiquzzaman M, Alam MM, Naidu VG. Synthesis, docking, in vitro and in vivo antidiabetic activity of pyrazole-based 2,4-thiazolidinedione derivatives as PPAR-γ modulators. Arch Pharm (Weinheim). 2018;351(3–4):e1700223.
Li G, Cheng Y, Han C, Song C, Huang N, Du Y. Pyrazole-containing pharmaceuticals: target, pharmacological activity, and their SAR studies. RSC Med Chem. 2022;13(11):1300–1321.
Bennani FE, Doudach L, Cherrah Y, Ramli Y, Karrouchi K, Faouzi ME. Overview of recent developments of pyrazole derivatives as anticancer agents in different cell lines. Bioorg Chem. 2020;97:103470.
Xu Z, Gao C, Ren QC, Song XF, Feng LS, Lv ZS. Recent advances of pyrazole-containing derivatives as anti-tubercular agents. Eur J Med Chem. 2017;139:429–440.
Naim MJ, Alam O, Nawaz F, Alam MJ, Alam P. Current status of pyrazole and its biological activities. J Pharm Bioallied Sci. 2016;8(1):2–17.
Meth-Cohn O, Stanforth SP. The Vilsmeier–Haack reaction. In: Trost BM, Fleming I, editors. Comprehensive Organic Synthesis. Oxford: Pergamon; 1991. p. 777–794.
Okhifo A, Ndukwe GI, Jack IR, Abayeh OJ. Synthesis and antimicrobial evaluation of some simple phenylhydrazones. J Chem Soc Nigeria. 2019;44(2):332–340.
Kumar A, Prakash O, Kinger M, Singh SP. Synthesis of some new 1-aryl-4-formyl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles using the Vilsmeier–Haack reaction: isolation of the key intermediate 1-aryl-3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)pyrazoles. Can J Chem. 2006;84:438–442.

How to cite this article

APA

MLA

Chicago

Vancouver

BibTeX

@article{DifarHA2024,
author = {Hussniya al Difar},
title = {Synthesis and Evaluation of Antimicrobial Activity of Some Heterocyclic Moieties of Pyrazole Derivatives},
journal = {International Journal of Chemical Synthesis and Chemical Reactions},
year = {2024},
volume = {10},
number = {01},
pages = {26--36},
issn = {2582-5917},
url = {https://journalspub.com/publication/uncategorized/article=10605}
}

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