Synthesis and Antimicrobial Evaluation of (E)-2-(4-((4-((1-(2,4-Dichlorophenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)methyl)-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamide Derivatives

被引:1
作者
Mascarenhas, Cheryl T. [1 ]
Wable, Jaidip B. [2 ]
Akolkar, Hemantkumar N. [3 ]
Darekar, Nirmala R. [4 ]
Prabhu, Pradnya J. [1 ]
机构
[1] K J Somaiya Coll Sci & Commerce, Dept Chem, Mumbai 400077, India
[2] VP Ms BN Bandodkar Coll Sci, Dept Chem, Thana 400601, India
[3] Abasaheb Marathe Arts & New Commerce Sci Coll, Dept Chem, Rajapur 416702, Maharashtra, India
[4] Radhabai Kale Mahila Mahavidyalaya, Dept Chem, Ahmednagar 414001, India
关键词
Click chemistry; Knoevenagel condensation; pyrazolone; 1,2,3-triazole; antimicrobial; BIOLOGICAL EVALUATION; CHALCONE; PYRAZOLE; TRIAZOLES;
D O I
10.1134/S1068162025010091
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Objective: There has never been a compilation of (E)-2-(4-((4-((1-(2,4-dichlorophenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)methyl)-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenylacetamide derivatives produced before. For the synthesis of (VIIa-VIIh), (E)-1-(2,4-dichlorophenyl)-4-(3-methoxy-4-(prop-2-yn-1-yloxy)benzylidene)-3-methyl-1H-pyrazol-5(4H)-one (V) was utilized. Methods: The compounds were synthesized using the Click chemistry process. We used the tube-dilution approach to test for antimicrobial and antifungal activity. Results and Discussion: Mass spectrometry, H-1, C-13 NMR, and IR spectroscopy were used to validate the eight newly produced compounds. The antibacterial and antifungal properties of the new compounds were tested. While seven compounds ((VIIa-VIIc), (VIIe-VIIh)) demonstrated antimicrobial activity against a range of bacterial strains, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes, the activity was comparable to that of the drug ampicillin, whereas (VIIh) exhibited good antifungal activity compared to its standard drug Griseofulvin against Candida albicans. Conclusions: We conclude that the newly synthesized 1,2,3-triazoles showed good antibacterial activity and can be used as precursors for drug molecules in the future.
引用
收藏
页码:151 / 159
页数:9
相关论文
共 24 条
[1]   Studies on Photophysical and Biological Activity of Newly Synthesized of 4-Methylpiperidin-4-ol Substituted Pyrazole Derivatives [J].
Al-Hazmi, Ghaferah H. ;
Marrakkur, Vidyagayatri ;
Naik, Lohit ;
Refat, Moamen S. .
POLISH JOURNAL OF ENVIRONMENTAL STUDIES, 2024, 33 (05) :5557-5565
[2]   Novel pyrazole derivatives as potential promising anti-inflammatory antimicrobial agents [J].
Bekhit, AA ;
Ashour, HMA ;
Guemei, AA .
ARCHIV DER PHARMAZIE, 2005, 338 (04) :167-174
[3]   Convenient Synthesis of Novel Chalcone and Pyrazoline Sulfonamide Derivatives as Potential Antibacterial Agents [J].
Bonakdar, A. P. S. ;
Sadeghi, A. ;
Aghaei, H. R. ;
Beheshtimaal, K. ;
Nazifi, S. M. R. ;
Massah, A. R. .
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2020, 46 (03) :371-381
[4]  
Bonakdara A.P.S., 2020, J. Saudi Chem. Soc, V24, P251, DOI [10.1016/j.jscs.2019.12.001, DOI 10.1016/J.JSCS.2019.12.001]
[5]  
Calderon Abram, 2020, Oncotarget, V11, P4224, DOI 10.18632/oncotarget.27815
[6]  
Camarasa Maria-Jose, 2005, Antiviral Chemistry & Chemotherapy, V16, P147
[7]   Synthesis, Characterization, and Antitumor Activity of Water-Soluble (Arene)ruthenium(II) Derivatives of 1,3-Dimethyl-4-acylpyrazolon-5-ato Ligands. First Example of Ru(arene)(ligand) Antitumor Species Involving Simultaneous Ru-N7(guanine) Bonding and Ligand Intercalation to DNA [J].
Caruso, Francesco ;
Monti, Elena ;
Matthews, Julian ;
Rossi, Miriam ;
Gariboldi, Marzia Bruna ;
Pettinari, Claudio ;
Pettinari, Riccardo ;
Marchetti, Fabio .
INORGANIC CHEMISTRY, 2014, 53 (07) :3668-3677
[8]   Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity [J].
Chinthala, Yakaiah ;
Thakur, Sneha ;
Tirunagari, Shalini ;
Chinde, Srinivas ;
Domatti, Anand Kumar ;
Arigari, Niranjana Kumar ;
Srinivas, K. V. N. S. ;
Alam, Sarfaraz ;
Jonnala, Kotesh Kumar ;
Khan, Feroz ;
Tiwari, Ashok ;
Grover, Paramjit .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 93 :564-573
[9]  
Darekar NR, 2022, INDIAN J HETEROCY CH, V32, P433
[10]   Synthesis of 3-(trifluoromethyl)-1-(perfluorophenyl)-1H-pyrazol-5(4H)-one derivatives via Knoevenagel condensation and their biological evaluation [J].
Dengale, Sujata G. ;
Akolkar, Hemantkumar N. ;
Karale, Bhausaheb K. ;
Darekar, Nirmala R. ;
Mhaske, Sadhana D. ;
Shaikh, Mubarak H. ;
Raut, Dipak N. ;
Deshmukh, Keshav K. .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2021, 68 (04) :657-668