Development of 4-aminoquinoline-1,3,5-triazine conjugates as potent antibacterial agent through facile synthetic route

Medicinal Chemistry Research

Volumn 22, Issue 10, 2013, Pages 5056-5065

  Bhat, Hans Raj ^a   Pandey, Pankaj Kumar ^a   Ghosh, Surajit Kumar ^b   Singh, Udaya Pratap ^a,c  

^a SAM HIGGINBOTTOM UNIVERSITY OF AGRICULTURE   (India)

^b DIBRUGARH UNIVERSITY   (India)

^c UNIVERSITY OF TARTU   (Estonia)

Author keywords

1,3,5 Triazine; 4 Aminoquinoline; Antibacterial

Indexed keywords

2 (4 CHLORO 6 [(4 NITROPHENYL)AMINO] 1,3,5 TRIAZIN 2 YL)HYDRAZINECARBOXAMIDE; 2 (4 CHLORO 6 [(4 NITROPHENYL)AMINO] 1,3,5 TRIAZIN2 YL]HYDRAZINECARBOTHIOAMIDE; 2 [4 [(4 NITROPHENYL)AMINO] 6 (PIPERAZIN 1 YL) 1,3,5 TRIAZIN 2 YL]HYDRAZINECARBOTHIOAMIDE; 2 [4 [(4 NITROPHENYL)AMINO] 6 (PIPERAZIN 1 YL) 1,3,5 TRIAZIN 2 YL]HYDRAZINECARBOXAMIDE; 4 [4 (2 CARBAMOTHIOYLHYDRAZINYL) 6 [(4 NITROPHENYL)AMINO] 1,3,5 TRIAZIN 2 YL] N (7 CHLOROQUINOLIN 4 YL)PIPERAZINE 1 CARBOTHIOAMIDE; 4 [[4 [(4 NITROPHENYL)AMINO] 6 (PIPERAZIN 1 YL) 1,3,5 TRIAZIN 2 YL]AMINO]PHENOL; 4 [[4 CHLORO 6 [(4 NITROPHENYL)AMINO] 1,3,5 TRIAZIN 2 YL]AMINO]PHENOL; 4 AMINOQUINOLINE 1,3,5 TRIAZINE DERIVATIVE; 4 AMINOQUINOLINE DERIVATIVE; 4 CHLORO 6 HYDRAZINYL N (4 NITROPHENYL) 1,3,5 TRIAZIN 2 AMINE HYDRATE; 4 CHLORO 6 MORPHOLINO N (4 NITROPHENYL) 1,3,5 TRIAZIN 2 AMINE; 4 HYDRAZINYL N (4 NITROPHENYL) 6 (PIPERAZIN 1 YL) 1,3,5 TRIAZIN 2 AMINE HYDRATE; 4 MORPHOLINO N (4 NITROPHENYL) 6 (PIPERAZIN 1 YL) 1,3,5 TRIAZIN 2 AMINE; 4,6 DICHLORO N (4 NITROPHENYL) 1,3,5 TRIAZIN 2 AMINE; 6 CHLORO N2 (4 NITROPHENYL) N4 (4 TOLYL) 1,3,5 TRIAZINE 2,4 DIAMINE; 6 CHLORO N2 (4 NITROPHENYL) N4 (O TOLYL) 1,3,5 TRIAZINE 2,4 DIAMINE; 6 CHLORO N2 (4 NITROPHENYL) N4 PHENYL 1,3,5 TRIAZINE 2,4 DIAMINE; 7 CHLORO 4 ISOTHIOCYANATOQUINOLINE; ANTIINFECTIVE AGENT; N (7 CHLOROQUINOLIN 4 YL) 4 [4 [(4 NITROPHENYL)AMINO] 6 (8 TOLYLAMINO) 1,3,5 TRIAZIN 2 YL]PIPERAZINE 1 CARBOTHIOAMIDE; N (7 CHLOROQUINOLIN 4 YL) 4 [4 [(4 NITROPHENYL)AMINO] 6 (PHENYLAMINO) 1,3,5 TRIAZIN 2 YL]PIPERAZINE 1 CARBOTHIOAMIDE; N (7 CHLOROQUINOLIN 4 YL) 4 [4 HYDRAZINYL 6 [(4 NITROPHENYL)AMINO] 1,3,5 TRIAZIN 2 YL]PIPERAZINE 1 CARBOTHIOAMIDE HYDRATE; N (7 CHLOROQUINOLIN 4 YL) 4 [4 MORPHOLINO 6 [(4-NITROPHENYL) AMINO] 1,3,5 TRIAZIN 2 YL]PIPERAZINE 1 CARBOTHIOAMIDE; N2 (3 AMINOPROPYL) 6 CHLORO N4 (4 NITROPHENYL) 1,3,5 TRIAZINE 2,4 DIAMINE; N2 (3 AMINOPROPYL) N4 (4 NITROPHENYL) 6 (PIPERAZIN 1 YL) 1,3,5 TRIAZINE 2,4 DIAMINE; N2 (4 NITROPHENYL) 6 (PIPERAZIN 1 YL) N4 (4 TOLYL) 1,3,5 TRIAZINE 2,4 DIAMINE; N2 (4 NITROPHENYL) 6 (PIPERAZIN 1 YL) N4 (8 TOLYL) 1,3,5 TRIAZINE 2,4 DIAMINE; N2 (4 NITROPHENYL) N4 PHENYL 6 (PIPERAZIN 1 YL) 1,3,5 TRIAZINE 2,4 DIAMINE; OFLOXACIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACILLUS SUBTILIS; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; MOLECULE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEUS MIRABILIS; PROTEUS VULGARIS; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84883460560     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0521-8     Document Type: Article

References (21)

1. Alanis AJ (2005) Resistance to antibiotics: are we in the post-antibiotic era. Arch Med Res 36:697-705
2. Bhat HR, Singh UP, Yadav PS, Kumar V, Das A, Chetia D, Prakash A, Mahanta J (2011) Synthesis, characterization and antimalarial activity of hybrid 4-aminoquinoline-1,3,5-triazine derivatives. Arabian J Chem. doi: 10.1016/j.arabjc.2011.07.001
3. Bhat HR, Ghosh SK, Prakash A, Gogoi K, Singh UP (2012a) In vitro antimalarial activity and molecular docking analysis of 4-aminoquinoline-clubbed 1,3,5-triazine derivatives. Lett Appl Microbiol 54:483-486
4. Bhat HR, Gupta SK, Singh UP (2012b) Discovery of potent, novel antibacterial hybrid conjugates from 4-aminoquinoline and 1,3,5-triazine: design, synthesis and antibacterial evaluation. RSC Adv 2:12690-12695
5. Bhat HR, Singh UP, Gahtori P, Ghosh SK, Gogoi K, Prakash A, Singh RK (2013) Antimalarial activity and docking studies of novel bi-functional hybrids derived from 4-aminoquinoline and 1,3,5-triazine against wild and mutant malaria parasites as pf-DHFR inhibitor. RSC Adv. doi: 10.1039/C2RA21915H
6. Corbett TH, Leopold WR, Dykes DJ, Roberts BJ, Griswold DP Jr, Schabel FM Jr (1982) Toxicity and anticancer activity of a new triazine antifolate (NSC 127755). Cancer Res 42:1707-1715
7. Davies J, Davies D (2010) Origins and evolution of antibiotic resistance. Microbiol Mol Biol 74:417-733
8. Dubey V, Pathak M, Bhat HR, Singh UP (2012) Design, facile synthesis and antibacterial activity of hybrid 1,3,4-thiadiazole-1,3,5-triazine derivatives tethered via S-bridge. Chem Biol Drug Des 80:598-604
9. Gahtori P, Ghosh SK, Singh B, Singh UP, Bhat HR, Uppal A (2012) Synthesis, SAR and antibacterial activity of hybrid chloro, dichloro- phenylthiazolyl-s-triazines. Saudi Pharm J 20:35-43
10. Ghosh SK, Saha A, Hazarika B, Singh UP, Bhat HR, Gahtori P (2012) Design, facile synthesis, antibacterial activity and structure-activity relationship of novel di- and tri-substituted 1,3,5-triazines. Lett Drug Des Dis 9:329-335
11. Junejo JA, Ghosh SK, Shaikh M, Gahtori P, Singh UP (2011) Facile synthesis, antibacterial activity and molecular properties prediction of Some new 1,3-dihydroimidazol-2-thione derivatives. Lett Drug Des Dis 8:763-768
12. Kumar S, Bhat HR, Kumawat MK, Singh UP (2013) Design and one-pot synthesis of hybrid thiazolidin-4-one-1,3,5-triazines as potent antibacterial agent against human disease causing pathogens. New J Chem. doi: 10.1039/C2NJ41028A
13. Lozano V, Aguado L, Hoorelbeke B, Renders M, Camarasa MJ, Schols D, Balzarini J, San-Félix A, Pérez-Pérez MJ (2011) Targeting HIV entry through interaction with envelope glycoprotein 120 (gp120): synthesis and antiviral evaluation of 1,3,5-triazines with aromatic amino acids. J Med Chem 54:5335-5348
14. Martinez JL, Baquero F (2000) Mutation frequencies and antibiotic resistance. Antimicrob Agents Chemother 44:1771-1777
15. National Committee for Clinical Laboratory Standards (1982) Standard methods for dilution antimicrobial susceptibility test for bacteria which grow aerobically. NCCLS, Villanova, p 242
16. Shapiro RS, Robbins N, Cowen LE (2011) Regulatory circuitry governing fungal development, drug resistance, and disease. Microbiol Mol Biol Rev 75:213-267
17. Singh UP, Singh RK, Bhat HR, Subhaschandra YP, Kumar V, Kumawat MK, Gahtori P (2011) Synthesis and antibacterial evaluation of a series of novel trisubstituted-s-triazines derivatives. Med Chem Res 20:1603-1610
18. Singh UP, Bhat HR, Gahtori P (2012a) Antifungal activity, SAR and physicochemical correlation of some thiazole-1,3,5-triazine derivatives. J Mycol Med 22:134-141
19. Singh UP, Pathak M, Dubey V, Bhat HR, Gahtori P, Singh RK (2012b) Design, synthesis, antibacterial activity and molecular docking studies on novel hybrid 1,3-thiazine-1,3,5-triazine derivatives as potential bacterial translation inhibitor. Chem Biol Drug Des 80:572-583
20. Singh UP, Bhat HR, Gahtori P, Singh RK (2013) Hybrid thiazole-1,3,5- triazines target cytosolic Leucyl-tRNA synthetase for antifungal action revealed by molecular docking studies. In Silico Pharmacology, In press
21. Singh UP, Bhat HR, Singh RK (2013b) Ceric ammonium nitrate catalysed expeditious one-pot synthesis of 1,3-thiazine as IspE kinase inhibitor of gram-negative bacteria using polyethylene glycol (PEG-400) as an efficient recyclable reaction medium. C. R. Chime. doi: 10.1016/j.crci.2012.11.019