Synthesis and Antimicrobial Activity of Substituted Amino-1H-Pyrazoles

被引:0
作者
Meshcheryakova, A. A. [1 ]
Konstantinova, E. A. [1 ,2 ]
Borisova, S. V. [3 ]
Burygin, G. L. [1 ,2 ]
Sorokin, V. V. [1 ]
机构
[1] Chernyshevsky Saratov Natl Res State Univ, Inst Chem, 83 Astrakhanskaya St, Saratov 410012, Russia
[2] Russian Acad Sci, Inst Biochem & Physiol Plants & Microorganisms, Autonomous Struct Subdiv FRC Saratov Sci Ctr, 13 Prosp Entuziastov, Saratov 410049, Russia
[3] VI Razumovsky Saratov State Med Univ, Minist Hlth Russia, 112 Bolshaya Kazachya St, Saratov 410012, Russia
关键词
substituted amino-1H-pyrazolecarbonitriles; substituted amino-1H-pyrazolecarboxamides; three-component one-step synthesis; antibacterial activity; 3-COMPONENT SYNTHESIS; POLARIZED ETHYLENES; PYRAZOLES; DITHIOCARBOXYLATES; INHIBITORS; THIOAMIDES;
D O I
10.1007/s11094-025-03358-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Substituted amino-1H-pyrazoles have been synthesized and characterized in terms of their antimicrobial ac- tivity. A three-component synthesis was carried out using a simple environmentally friendly one-step method starting from aromatic aldehydes, hydrazines or benzhydrazides, malononitrile or cyanoacetic acid amide and water or a mixture of water-i-PrOH as the solvent. The antimicrobial properties of the synthesized com- pounds, including previously unknown ones, were determined against Gram-negative and Gram-positive bac- teria. 5-Amino-1-(2,4-dinitrophenyl)-3-aryl-1H-pyrazole-4-carboxylates with 3-nitrophenyl or 3-hydroxy- phenyl substituents showed pronounced antimicrobial activity against Pseudomonas aeruginosa. The results indicated that further searching for antimicrobial compounds in the series of aryl-substituted amino-1H-pyrazolecarbonitriles and amino-1H-pyrazolecarboxamides was promising.
引用
收藏
页码:21 / 26
页数:6
相关论文
共 16 条
[1]   Synthesis of 5-Substituted 3-Amino-1H-Pyrazole-4-Carbonitriles as Precursors for Microwave Assisted Regiospecific Syntheses of Pyrazolo[1,5-a]Pyrimidines [J].
Al-Qalaf, Fawzia ;
Mandani, Faisal ;
Abdelkhalik, Mervat Mohammed ;
Bassam, Abeer Abdulrahman .
MOLECULES, 2009, 14 (01) :78-88
[2]  
Amalchieva O. A., 2006, ZH ORG KHIM, V42, P1358
[3]   Targeted polypharmacology: discovery of dual inhibitors of tyrosine and phosphoinositide kinases [J].
Apsel, Beth ;
Blair, Jimmy A. ;
Gonzalez, Beatriz ;
Nazif, Tamim M. ;
Feldman, Morri E. ;
Aizenstein, Brian ;
Hoffman, Randy ;
Williams, Roger L. ;
Shokat, Kevan M. ;
Knight, Zachary A. .
NATURE CHEMICAL BIOLOGY, 2008, 4 (11) :691-699
[4]   A New Pathway for the Preparation of Pyrano[2,3-c]pyrazoles and molecular Docking as Inhibitors of p38 MAP Kinase [J].
Hai Truong Nguyen ;
Minh-Nhat Ha Truong ;
Tan Van Le ;
Nam Tri Vo ;
Hoang Duc Nguyen ;
Phuong Hoang Tran .
ACS OMEGA, 2022, 7 (20) :17432-17443
[5]   One-Pot of Three-Component Synthesis of Novel Biologically Important 5-Amino-1,3-Diaryl-1H-pyrazole-4-Carbonitriles using L-Proline Catalyst and their Antimicrobial Activity [J].
Heravi, Mohammad Reza Poor ;
Danafar, Mahdis ;
Heravi, Niloofar Poor .
LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (11) :922-930
[6]   The conversion of isothiazoles into pyrazoles using hydrazine [J].
Ioannidou, Heraklidia A. ;
Koutentis, Panayiotis A. .
TETRAHEDRON, 2009, 65 (34) :7023-7037
[7]   Green and efficient three-component synthesis of novel isoniazid pyrazoles, molecular docking, antioxidant and antitubercular evaluation [J].
Koli, Bharti P. ;
Gore, Rambhau P. ;
Malasane, Pravin R. .
SYNTHETIC COMMUNICATIONS, 2023, 53 (18) :1506-1519
[8]   Three-Component Synthesis of Spiropyrazolines Derived from Benzohydrazides [J].
Meshcheryakova, A. A. ;
Neumoina, K. S. ;
Sorokin, V. V. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (08) :1309-1314
[9]   Synthesis and biological activity of a new class of enaminonitrile pyrazole [J].
Mohamed, Sabah S. ;
Dauoud, Nadia T. ;
Shaban, Sara N. ;
Abdelghaffar, Nahed F. ;
Sayed, Galal H. ;
Anwer, Kurls E. .
EGYPTIAN JOURNAL OF CHEMISTRY, 2021, 64 (06) :3187-3203
[10]  
Sangwan S., 2021, CURR RES GREEN SUSTA, V4, DOI DOI 10.1016/J.CRGSC.2021.100146