Design, synthesis, and biological evaluations of (E)-2-(1-[2-mercapto-4-methyl-1-phenyl-1H-imidazol-5-yl]ethylidene)hydrazinecarbothioamide derivatives as antimicrobial agents

被引:0
作者
Daraji, Drashti G. [1 ]
Rajani, Dhanji P. [2 ,3 ]
Jayanthi, Sivaraman [4 ]
Patel, Hitesh D. [1 ]
机构
[1] Gujarat Univ, Sch Sci, Dept Chem, Navarangpura, Gujarat, India
[2] Microcare Lab, Surat, India
[3] TRC, Surat, India
[4] Vellore Inst Technol, Sch Bio Sci & Technol, Vellore, Tamil Nadu, India
关键词
MICROWAVE-ASSISTED SYNTHESIS; DIHYDROPTEROATE SYNTHASE; MOLECULAR DOCKING; CRYSTAL-STRUCTURES; ANTIBACTERIAL; DHPS; ANTIOXIDANT; INHIBITION; COMPLEX;
D O I
10.1002/jhet.4378
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In recent year, the development of new drugs as antibacterial agents is an important resolution to overcome drug-resistant pathogens. Imidazole derivatives were synthesized using the microwave irradiation method and were characterized using spectral analysis techniques such as proton nuclear magnetic resonance, mass, and Fourier transform infrared spectroscopy. All the analogous were assessed for their in vitro antimicrobial activity and in silico; minimum inhibition concentration values of some conjugates were evaluated against extended spectrum beta-lactamases, vancomycin-resistant enterococci, and Methicillin-resistant Staphylococcus aureus strains from clinical samples. All the analogous were used as ligands in molecular docking and adsorption, distribution, metabolism, and excretion against saDHPS. Furthermore, compounds were also examined for their in vitro antituberculosis and antimalarial activity.
引用
收藏
页码:178 / 193
页数:16
相关论文
共 39 条
[1]  
[Anonymous], 2014, Desmond Molecular Dynamics System
[2]   Crystal structure of Mycobacterium tuberculosis 6-hydroxymethyl-7,8-dihydropteroate synthase in complex with pterin monophosphate:: New insight into the enzymatic mechanism and sulfa-drug action [J].
Baca, AM ;
Sirawaraporn, R ;
Turley, S ;
Sirawaraporn, W ;
Hol, WGJ .
JOURNAL OF MOLECULAR BIOLOGY, 2000, 302 (05) :1193-1212
[3]   Synthesis and antioxidant activities of transition metal complexes based 3-hydroxysalicylaldehyde-S-methylthiosemicarbazone [J].
Bal-Demirci, Tillay ;
Sahin, Musa ;
Kondakci, Esin ;
Ozyurek, Mustafa ;
Ulkuseven, Bahri ;
Apak, Resat .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 138 :866-872
[4]   Molecular docking studies and facile synthesis of most potent biologically active N-tert-butyl-4-(4-substituted phenyl)-2-((substituted-2-oxo-2H-chromen-4-yl)methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxamide hybrids: An approach for microwave-assisted syntheses and biological evaluation [J].
Chavan, Rakesh R. ;
Hosamani, Kallappa M. ;
Kulkarni, Badarinath D. ;
Joshi, Shrinivas D. .
BIOORGANIC CHEMISTRY, 2018, 78 :185-194
[5]   Structure of S. aureus HPPK and the Discovery of a New Substrate Site Inhibitor [J].
Chhabra, Sandeep ;
Dolezal, Olan ;
Collins, Brett M. ;
Newman, Janet ;
Simpson, Jamie S. ;
Macreadie, Ian G. ;
Fernley, Ross ;
Peat, Thomas S. ;
Swarbrick, James D. .
PLOS ONE, 2012, 7 (01)
[6]   Synthesis, In Vitro Biological Screening, and In Silico Computational Studies of Some Novel Imidazole-2-thiol Derivatives [J].
Daraji, Drashti G. ;
Patel, Kinjal D. ;
Patel, Hitesh D. ;
Rajani, Dhanji P. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (02) :539-551
[7]   Computational insights into factor affecting the potency of diaryl sulfone analogs as Escherichia coli dihydropteroate synthase inhibitors [J].
Das, Bratin Kumar ;
Pushyaraga, P., V ;
Chakraborty, Debashree .
COMPUTATIONAL BIOLOGY AND CHEMISTRY, 2019, 78 :37-52
[8]   A Placebo-Controlled Trial of Antibiotics for Smaller Skin Abscesses [J].
Daum, Robert S. ;
Miller, Loren G. ;
Immergluck, Lilly ;
Fritz, Stephanie ;
Creech, C. Buddy ;
Young, David ;
Kumar, Neha ;
Downing, Michele ;
Pettibone, Stephanie ;
Hoagland, Rebecca ;
Eells, Samantha J. ;
Boyle, Mary G. ;
Parker, Trisha Chan ;
Chambers, Henry F. .
NEW ENGLAND JOURNAL OF MEDICINE, 2017, 376 (26) :2545-2555
[9]  
DeFrancesco L., NAT BIOTECHNOL, V30, P333
[10]   In vitro evaluation of the activity of thiosemicarbazone derivatives against mycotoxigenic fungi affecting cereals [J].
Degola, Francesca ;
Morcia, Caterina ;
Bisceglie, Franco ;
Mussi, Francesca ;
Tumino, Giorgio ;
Ghizzoni, Roberta ;
Pelosi, Giorgio ;
Terzi, Valeria ;
Buschini, Annamaria ;
Restivo, Francesco Maria ;
Lodi, Tiziana .
INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY, 2015, 200 :104-111