Microwave Irradiated Synthesis of Pyrimidine Containing, Thiazolidin-4-ones: Antimicrobial, Anti-Tuberculosis, Antimalarial and Anti-Protozoa Evaluation

被引:6
作者
Soni, Hetal, I [1 ,2 ]
Patel, Navin B. [3 ]
Parmar, Rahul B. [4 ]
Chan-Bacab, Manuel J. [5 ]
Rivera, Gildardo [6 ]
机构
[1] CB Patel Comp Coll, Surat 395017, Gujarat, India
[2] JNM Patel Sci Coll, Surat 395017, Gujarat, India
[3] Veer Narmad South Gujarat Univ, Dept Chem, Organ Res Lab, Udhana Magdalla Rd, Surat 395007, Gujarat, India
[4] Atmanand Saraswati Sci Coll, Surat 395006, Gujarat, India
[5] Univ Autonoma Campeche, Dept Microbiol Ambientaly Biotecnol, Av Agustin Melgar S-N, Campeche, Mexico
[6] Inst Politecn Nacl, Ctr Biotecnol Genom, Lab Biotecnol Farmaceut, Reynosa 88710, Mexico
关键词
Thiazolidin-4-ones; antibacterial; antifungal; anti-tubercular H37RV; antimalarial; anti-protozoa; PLASMODIUM-FALCIPARUM; DERIVATIVES; ANTIBACTERIAL; DESIGN; 4-THIAZOLIDINONES; AZETIDINONE; ANALOGS; AGENTS;
D O I
10.2174/1570178619666220111124104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aims: This study aims to synthesize thiazolidine-4-one compounds with a pyrimidine nucleus and evaluate against different species of bacteria, fungi, protozoa, and the malaria parasite. Background: Microwave irradiation was the best method for synthesizing the thiazolidin-4-one ring system. It took only 15 minutes for synthesizing thiazolidin-4-one while the conventional method required 12 hours. The rapid reaction was the main concern of this research. Objective: Pyrimidine and Thiazolidin-4-one nucleus have broad-spectrum biological activity and when it is introduced with other hetero atoms containing moiety, many types of biological activities have been found; antimicrobial, anti-tuberculosis, anti-protozoa, antimalarial are the main activities. The activity of these compounds inspired us to do extra research on Thiazolidin-4-one fused pyrimidines with different functional groups. The aim of this study is to synthesize a combination of these two ring systems in less time by using a microwave irradiation method and to evaluate new compounds for different bioactivity. Methods: 2-(4-Chlorophenyl)-3-(4-(substituted phenyl)-6-(substituted aryl) pyrimidin-2-yl) thiazolidin-4-ones (6(A-J)) were synthesized by microwave irradiation to save energy and time. The structure of all newly synthesized motifs was characterized by spectral analysis (H-1 NMR, C-13 NMR, IR, spectroscopy) and screened for antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes, antifungal activity against Candida albicans, Aspergillus niger, Aspergillus clavatus, anti-tuberculosis activity against M. tuberculosis H37RV, antimalarial activity against Plasmodium falciparum and anti-protozoa activity against L. mexicana and T. cruzi. Results: Because of microwave irradiation synthesis, time period is very less for preparing the new compound. Biological response given by compounds 6(B,) 6(C), 6(D), 6(E), 6(G), 6(H), and 6(J) was found excellent. Conclusion: Good yield with purity of the newly synthesized thiazolidine-4-one compounds obtained in less time by using microwave irradiation. The biological response of some of the compounds of this series was found excellent.
引用
收藏
页码:731 / 738
页数:8
相关论文
共 42 条
[1]   COMPARISON OF IMPROVED BACTEC AND LOWENSTEIN-JENSEN MEDIA FOR CULTURE OF MYCOBACTERIA FROM CLINICAL SPECIMENS [J].
ANARGYROS, P ;
ASTILL, DSJ ;
LIM, ISL .
JOURNAL OF CLINICAL MICROBIOLOGY, 1990, 28 (06) :1288-1291
[2]  
[Anonymous], 1997, M27A NCCLS
[3]  
Barbaros E., 2016, IRAN J PHARM RES, V15, P783, DOI [10.22037/IJPR.2016.1911, DOI 10.22037/IJPR.2016.1911]
[4]   Microwave Assisted Synthesis, Characterization and Antimicrobial Screening of Thiazolidin-4-one Substituted Pyrazole Derivatives [J].
Beniwal, Meenu ;
Jain, Neelam .
CURRENT MICROWAVE CHEMISTRY, 2019, 6 (01) :44-53
[5]   Synthesis and biological evaluation of anti-Toxoplasma gondii activity of a novel scaffold of thiazolidinone derivatives [J].
Carradori, Simone ;
Secci, Daniela ;
Bizzarri, Bruna ;
Chimenti, Paola ;
De Monte, Celeste ;
Guglielmi, Paolo ;
Campestre, Cristina ;
Rivanera, Daniela ;
Bordon, Claudia ;
Jones-Brando, Lorraine .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2017, 32 (01) :746-758
[6]   DESIGN, SYNTHESIS AND IN-SILICO STUDY OF NOVEL SERIES OF 2-PHENYL-3-(5-SULFANYL-1,3,4-THIADIAZOL-2-YL)-1,3-THIAZOLIDIN-4-ONE DERIVATIVES WITH POTENTIAL ANTI-TUBERCULAR ACTIVITY [J].
Dadlani, V. G. ;
Somani, R. R. ;
Tripathi, P. K. .
INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2019, 10 (05) :2565-2576
[7]   Synthesis of thiazolidin-4-ones and thiazinan-4-ones from 1-(2-aminoethyl)pyrrolidine as acetylcholinesterase inhibitors [J].
das Neves, Adriana M. ;
Berwaldt, Gabriele A. ;
Avila, Cinara T. ;
Goulart, Tais B. ;
Moreira, Bruna C. ;
Ferreira, This P. ;
Soares, Mayara S. P. ;
Pedra, Nathalia S. ;
Spohr, Luiza ;
dE Souza, Anita A. A. ;
Spanevello, Roselia M. ;
Cunico, Wilson .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2020, 35 (01) :31-41
[8]  
De Carvalho L.P., 2014, J DEV DRUGS, V3, P1, DOI [10.4172/2329-6631.1000126, DOI 10.4172/2329-6631.1000126]
[9]   Dicationic liquid mediated synthesis of tetrazoloquinolinyl methoxy phenyl 4-thiazolidinones and their antibacterial and antitubercular evaluation [J].
Deshmukh, Amarsinh R. ;
Dhumal, Sambhaji T. ;
Nawale, Laxman U. ;
Khedkar, Vijay M. ;
Sarkar, Dhiman ;
Mane, Ramrao A. .
SYNTHETIC COMMUNICATIONS, 2019, 49 (04) :587-601
[10]  
Desjardins R. E., 1984, Antimalarial drugs. 1: Biological background, experimental methods, and drug resistance. (Handbook of Experimental Pharmacology, Volume 68 No. 1.), P179