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Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3c]quinazoline – pyrazoline hybrids

Yıl 2022, Cilt: 26 Sayı: 1, 28 - 34, 28.06.2025

Inna Nosulenko , Halyna Berest , Dmytro Skoryna , Oleksii Voskoboinik , Sergiy Kovalenko

Öz

Present manuscript describes the design, synthesis and antimicrobial activity of novel [1,2,4]triazіno[2,3-c]quinazoline – pyrazoline hybrids. The combination of pyrazoline cycle with [1,2,4]triazіno[2,3-c]quinazoline heterocyclic fragment was substantiated as promising approach for development of novel antibacterial and antifungal agents. The simple and effective synthetic procedure for target heterocyclic hybrids was proposed. The structures of obtained compounds were verified by appropriate physicochemical methods, the features of 1H NMR-spectral characteristics were described as well. It was shown that synthesized compounds reveal significant growth inhibitory activity against Candida albicans strain.

Anahtar Kelimeler

quinazoline pyrazoline heterocyclic hybrids antimicrobial activity Candida albicans

Kaynakça

  • [1] Nehra B, Rulhania S, Jaswal S, Kumar B, Singh G, Monga V. Recent advancements in the development of bioactive pyrazoline derivatives. Eur J Med Chem. 2020; 205: 112666. [CrossRef]
  • [2] Matiadis D, Sagnou M. Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview. Int J Mol Sci. 2020; 21(15): 5507. [CrossRef]
  • [3] Chimenti F, Carradori S, Secci D, Bolasco A, Bizzarri B, Chimenti P, Granese A, Yanez M, Orallo, F. Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)pyrazole derivatives. Eur J Med Chem. 2010; 45(2): 800–804. [CrossRef]
  • [4] Palaska E, Aydin F, Uçar G, Erol D. Synthesis and monoamine oxidase inhibitory activities of 1-thiocarbamoyl-3,5diphenyl-4,5-dihydro-1H-pyrazole derivatives. Arch Pharm. 2008; 341(4): 209–215. [CrossRef]
  • [5] Nepali K, Singh G, Turan A, Agarwal A, Sapra S, Kumar R, Dhar KL. A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors. Bioorg Med Chem. 2011; 19(6): 1950–1958. [CrossRef]
  • [6] Zhou Z, Zhuo J, Yan S, Ma L. Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors. Bioorg Med Chem. 2013; 21(7): 2156–2162. [CrossRef]
  • [7] Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R. Synthesis of new 4-thiazolidinone-, pyrazoline-, and isatin-based conjugates with promising antitumor activity. J Med Chem. 2012; 55(20): 8630–8641. [CrossRef]
  • [8] Sharma M, Sharma S, Buddhiraja A, Saxena AK, Nepali K, Bedi PMS. Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline—isatin hybrids. Med Chem Res. (2014); 23(10): 4337–4344. [CrossRef]
  • [9] Havrylyuk D, Kovach N, Zimenkovsky B, Vasylenko O, Lesyk R. Synthesis and anticancer activity of isatin-based pyrazolines and thiazolidines conjugates. Arch Pharm. 2011; 344(8): 514–522. [CrossRef]
  • [10] Garazd Y, Garazd M, Lesyk R. Synthesis and evaluation of anticancer activity of 6-pyrazolinylcoumarin derivatives. Saudi Pharm J. 2017; 25(2): 214–223. [CrossRef]
  • [11] Havrylyuk D, Zimenkovsky B, Karpenko O, Grellier P, Lesyk R. Synthesis of pyrazoline–thiazolidinone hybrids with trypanocidal activity. Eur J Med Chem. 2014; 85: 245–254. [CrossRef]
  • [12] Pathak V, Maurya HK, Sharma S, Srivastava KK, Gupta A Synthesis and biological evaluation of substituted 4,6-diarylpyrimidines and 3,5-diphenyl-4,5-dihydro-1H-pyrazoles as anti-tubercular agents. Bioorg Med Chem Lett. 2014; 24(13): 2892–2896. [CrossRef]
  • [13] Alex JM, Kumar R. 4,5-Dihydro-1H-pyrazole: an indispensable scaffold. J Enzyme Inhib Med Chem. 2013; 29(3): 427–442. [CrossRef]
  • [14] Havrylyuk D, Zimenkovsky B, Vasylenko O, Lesyk R. Synthesis and Anticancer and Antiviral Activities of New 2-Pyrazoline-Substituted 4-Thiazolidinones. J Heterocycl Chem. 2013; 50(S1): E55–E62. [CrossRef]
  • [15] Berest GG, Voskoboynik OY, Kovalenko SI, Nosulenko IS, Antypenko LM, Antypenko OM, Shvets VM, Katsev AM. Synthesis of new 6-{[ω-(dialkylamino(heterocyclyl)alkyl]thio}-3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones and evaluation of their anticancer and antimicrobial activities. Sci Pharm. 2012; 80(1): 37–65. [CrossRef]
  • [16] Nosulenko IS, Voskoboynik OY, Berest GG, Safronyuk SL, Kovalenko SI, Kamyshnyi OM, Polishchuk NM, Sinyak RS, Katsev AV. Synthesis and antimicrobial activity of 6-thioxo-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]quinazolin-2-one derivatives. Sci Pharm. 2014; 82(3): 483–500. [CrossRef]
  • [17] Breitmaier E, Structure Elucidation By NMR In Organic Chemistry: A Practical Guide, John Wiley &Sons, Ltd, 2002. [CrossRef]
  • [18] Balouiri M, Sadiki М, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: A review. J Pharm Anal 2016; 6(2): 71-79. [CrossRef]

Yıl 2022, Cilt: 26 Sayı: 1, 28 - 34, 28.06.2025

Inna Nosulenko , Halyna Berest , Dmytro Skoryna , Oleksii Voskoboinik , Sergiy Kovalenko

Öz

Kaynakça

  • [1] Nehra B, Rulhania S, Jaswal S, Kumar B, Singh G, Monga V. Recent advancements in the development of bioactive pyrazoline derivatives. Eur J Med Chem. 2020; 205: 112666. [CrossRef]
  • [2] Matiadis D, Sagnou M. Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview. Int J Mol Sci. 2020; 21(15): 5507. [CrossRef]
  • [3] Chimenti F, Carradori S, Secci D, Bolasco A, Bizzarri B, Chimenti P, Granese A, Yanez M, Orallo, F. Synthesis and inhibitory activity against human monoamine oxidase of N1-thiocarbamoyl-3,5-di(hetero)aryl-4,5-dihydro-(1H)pyrazole derivatives. Eur J Med Chem. 2010; 45(2): 800–804. [CrossRef]
  • [4] Palaska E, Aydin F, Uçar G, Erol D. Synthesis and monoamine oxidase inhibitory activities of 1-thiocarbamoyl-3,5diphenyl-4,5-dihydro-1H-pyrazole derivatives. Arch Pharm. 2008; 341(4): 209–215. [CrossRef]
  • [5] Nepali K, Singh G, Turan A, Agarwal A, Sapra S, Kumar R, Dhar KL. A rational approach for the design and synthesis of 1-acetyl-3,5-diaryl-4,5-dihydro(1H)pyrazoles as a new class of potential non-purine xanthine oxidase inhibitors. Bioorg Med Chem. 2011; 19(6): 1950–1958. [CrossRef]
  • [6] Zhou Z, Zhuo J, Yan S, Ma L. Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors. Bioorg Med Chem. 2013; 21(7): 2156–2162. [CrossRef]
  • [7] Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R. Synthesis of new 4-thiazolidinone-, pyrazoline-, and isatin-based conjugates with promising antitumor activity. J Med Chem. 2012; 55(20): 8630–8641. [CrossRef]
  • [8] Sharma M, Sharma S, Buddhiraja A, Saxena AK, Nepali K, Bedi PMS. Synthesis and cytotoxicity studies of 3,5-diaryl N-acetyl pyrazoline—isatin hybrids. Med Chem Res. (2014); 23(10): 4337–4344. [CrossRef]
  • [9] Havrylyuk D, Kovach N, Zimenkovsky B, Vasylenko O, Lesyk R. Synthesis and anticancer activity of isatin-based pyrazolines and thiazolidines conjugates. Arch Pharm. 2011; 344(8): 514–522. [CrossRef]
  • [10] Garazd Y, Garazd M, Lesyk R. Synthesis and evaluation of anticancer activity of 6-pyrazolinylcoumarin derivatives. Saudi Pharm J. 2017; 25(2): 214–223. [CrossRef]
  • [11] Havrylyuk D, Zimenkovsky B, Karpenko O, Grellier P, Lesyk R. Synthesis of pyrazoline–thiazolidinone hybrids with trypanocidal activity. Eur J Med Chem. 2014; 85: 245–254. [CrossRef]
  • [12] Pathak V, Maurya HK, Sharma S, Srivastava KK, Gupta A Synthesis and biological evaluation of substituted 4,6-diarylpyrimidines and 3,5-diphenyl-4,5-dihydro-1H-pyrazoles as anti-tubercular agents. Bioorg Med Chem Lett. 2014; 24(13): 2892–2896. [CrossRef]
  • [13] Alex JM, Kumar R. 4,5-Dihydro-1H-pyrazole: an indispensable scaffold. J Enzyme Inhib Med Chem. 2013; 29(3): 427–442. [CrossRef]
  • [14] Havrylyuk D, Zimenkovsky B, Vasylenko O, Lesyk R. Synthesis and Anticancer and Antiviral Activities of New 2-Pyrazoline-Substituted 4-Thiazolidinones. J Heterocycl Chem. 2013; 50(S1): E55–E62. [CrossRef]
  • [15] Berest GG, Voskoboynik OY, Kovalenko SI, Nosulenko IS, Antypenko LM, Antypenko OM, Shvets VM, Katsev AM. Synthesis of new 6-{[ω-(dialkylamino(heterocyclyl)alkyl]thio}-3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones and evaluation of their anticancer and antimicrobial activities. Sci Pharm. 2012; 80(1): 37–65. [CrossRef]
  • [16] Nosulenko IS, Voskoboynik OY, Berest GG, Safronyuk SL, Kovalenko SI, Kamyshnyi OM, Polishchuk NM, Sinyak RS, Katsev AV. Synthesis and antimicrobial activity of 6-thioxo-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]quinazolin-2-one derivatives. Sci Pharm. 2014; 82(3): 483–500. [CrossRef]
  • [17] Breitmaier E, Structure Elucidation By NMR In Organic Chemistry: A Practical Guide, John Wiley &Sons, Ltd, 2002. [CrossRef]
  • [18] Balouiri M, Sadiki М, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity: A review. J Pharm Anal 2016; 6(2): 71-79. [CrossRef]
Toplam 18 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık ve İlaç Bilimleri (Diğer)
Bölüm Articles
Yazarlar

Inna Nosulenko

Halyna Berest

Dmytro Skoryna

Oleksii Voskoboinik

Sergiy Kovalenko

Yayımlanma Tarihi 28 Haziran 2025
Yayımlandığı Sayı Yıl 2022 Cilt: 26 Sayı: 1

Kaynak Göster

APA Nosulenko, I., Berest, H., Skoryna, D., Voskoboinik, O., vd. (2025). Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3c]quinazoline – pyrazoline hybrids. Journal of Research in Pharmacy, 26(1), 28-34.
AMA Nosulenko I, Berest H, Skoryna D, Voskoboinik O, Kovalenko S. Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3c]quinazoline – pyrazoline hybrids. J. Res. Pharm. Haziran 2025;26(1):28-34.
Chicago Nosulenko, Inna, Halyna Berest, Dmytro Skoryna, Oleksii Voskoboinik, ve Sergiy Kovalenko. “Synthesis and Antimicrobial Activity of [1,2,4]triazіno[2,3c]quinazoline – Pyrazoline Hybrids”. Journal of Research in Pharmacy 26, sy. 1 (Haziran 2025): 28-34.
EndNote Nosulenko I, Berest H, Skoryna D, Voskoboinik O, Kovalenko S (01 Haziran 2025) Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3c]quinazoline – pyrazoline hybrids. Journal of Research in Pharmacy 26 1 28–34.
IEEE I. Nosulenko, H. Berest, D. Skoryna, O. Voskoboinik, ve S. Kovalenko, “Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3c]quinazoline – pyrazoline hybrids”, J. Res. Pharm., c. 26, sy. 1, ss. 28–34, 2025.
ISNAD Nosulenko, Inna vd. “Synthesis and Antimicrobial Activity of [1,2,4]triazіno[2,3c]quinazoline – Pyrazoline Hybrids”. Journal of Research in Pharmacy 26/1 (Haziran 2025), 28-34.
JAMA Nosulenko I, Berest H, Skoryna D, Voskoboinik O, Kovalenko S. Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3c]quinazoline – pyrazoline hybrids. J. Res. Pharm. 2025;26:28–34.
MLA Nosulenko, Inna vd. “Synthesis and Antimicrobial Activity of [1,2,4]triazіno[2,3c]quinazoline – Pyrazoline Hybrids”. Journal of Research in Pharmacy, c. 26, sy. 1, 2025, ss. 28-34.
Vancouver Nosulenko I, Berest H, Skoryna D, Voskoboinik O, Kovalenko S. Synthesis and antimicrobial activity of [1,2,4]triazіno[2,3c]quinazoline – pyrazoline hybrids. J. Res. Pharm. 2025;26(1):28-34.