Synthesis and in vitro antimicrobial evaluation of benzothiazolylindenopyrazoles

被引:4
作者
Mor, Satbir [1 ]
Khatri, Mohini [1 ]
Punia, Ravinder [1 ]
Jakhar, Komal [2 ]
机构
[1] Guru Jambheshwar Univ Sci & Technol, Dept Chem, Hisar 125001, Haryana, India
[2] Maharshi Dayanand Univ, Dept Chem, Rohtak 124001, Haryana, India
关键词
Indenopyrazoles; Biological activity; Antimicrobial; SAR; BIOLOGICAL EVALUATION; PYRAZOLE; AGENTS; HYDRAZINES; EFFICIENT; ANALOGS; DESIGN;
D O I
10.1007/s00044-022-02988-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In the present study, a series of benzothiazolylindenopyrazoles 5a-o has been efficiently synthesized by refluxing a solution of 2-(3-substitutedbenzoyl)-(1H)-indene-1,3(2H)-diones 1a-c and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles 4a-e in presence of dry ethanol and glacial acetic acid in good yields. The newly synthesized derivatives 5a-o were well characterized by using different physical and spectral techniques (FTIR, H-1 NMR, C-13 NMR and HRMS). All the derivatives 5a-o were subjected to their preliminary antimicrobial assay against two Gram-positive bacterial strains [Bacillus subtilis (MTCC 441) and Staphylococcus aureus (MTCC 7443)], two Gram-negative bacterial strains [Escherichia coli (MTCC 1652) and Pseudomonas aeruginosa (MTCC 424)], and two fungal strains [Candida albicans (MTCC 227) and Aspergillus niger (MTCC 8189)] employing serial dilution method using Ciprofloxacin and Fluconazole as standard drugs for bacterial and fungal strains, respectively. Among all the tested derivatives, 5m (MIC = 0.0255 mu mol/mL) and 5o (MIC = 0.0232 mu mol/mL) exhibited maximal inhibition against fungal strain C. albicans. Overall, the investigation revealed that the titled compounds were found more potent against C. albicans.
引用
收藏
页码:47 / 56
页数:10
相关论文
共 38 条
[1]   Synthesis and applications of bipyrazole systems [J].
Abdel-Wahab, Bakr F. ;
Dawood, Kamal M. .
ARKIVOC, 2012, :491-545
[2]   POMA analyses as new efficient bioinformatics' platform to predict and optimise bioactivity of synthesized 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues [J].
Ahsan, Mohamed Jawed ;
Govindasamy, Jeyabalan ;
Khalilullah, Habibullah ;
Mohan, Govind ;
Stables, James P. ;
Pannecouque, Christophe ;
De Clercq, Eric .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (23) :7029-7035
[3]   Synthesis and antimycobacterial evaluation of 3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide analogues [J].
Ahsan, Mohamed Jawed ;
Samy, Jeyabalan Govinda ;
Khalilullah, Habibullah ;
Bakht, Mohamed Afroz ;
Hassan, Mohd. Zaheen .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (11) :5694-5697
[4]   Discovery of novel antitubercular 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues [J].
Ahsan, Mohamed Jawed ;
Samy, Jeyabalan Govinda ;
Soni, Savita ;
Jain, Naresh ;
Kumar, Lalit ;
Sharma, Lalit K. ;
Yadav, Hemant ;
Saini, Lokesh ;
Kalyansing, Rajput Gopal ;
Devenda, Narendra S. ;
Prasad, Ravindra ;
Jain, Chandra Bhushan .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (18) :5259-5261
[5]   Indenopyrazole oxime ethers: Synthesis and β1-adrenergic blocking activity [J].
Angelone, Tommaso ;
Caruso, Anna ;
Rochais, Christophe ;
Caputo, Angela Maria ;
Cerra, Maria Carmela ;
Dallemagne, Patrick ;
Filice, Elisabetta ;
Genest, David ;
Pasqua, Teresa ;
Puoci, Francesco ;
Saturnino, Carmela ;
Sinicropi, Maria Stefania ;
El-Kashef, Hussein .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 :672-681
[6]   Review: biologically active pyrazole derivatives [J].
Ansari, Anam ;
Ali, Abad ;
Asif, Mohd ;
Shamsuzzaman .
NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) :16-41
[7]   Bad Bugs, No Drugs: No ESKAPE! An Update from the Infectious Diseases Society of America [J].
Boucher, Helen W. ;
Talbot, George H. ;
Bradley, John S. ;
Edwards, John E., Jr. ;
Gilbert, David ;
Rice, Louis B. ;
Scheld, Michael ;
Spellberg, Brad ;
Bartlett, John .
CLINICAL INFECTIOUS DISEASES, 2009, 48 (01) :1-12
[8]  
DHAWAN SN, 1994, INDIAN J CHEM B, V33, P38
[9]   Arylglyoxals in Synthesis of Heterocyclic Compounds [J].
Eftekhari-Sis, Bagher ;
Zirak, Maryam ;
Akbari, Ali .
CHEMICAL REVIEWS, 2013, 113 (05) :2958-3043
[10]   Recent developments in synthetic chemistry and biological activities of pyrazole derivatives [J].
Faisal, Muhammad ;
Saeed, Aamer ;
Hussain, Sarwat ;
Dar, Parsa ;
Larik, Fayaz Ali .
JOURNAL OF CHEMICAL SCIENCES, 2019, 131 (08)