Synthesis, antimalarial-, and antibacterial activity evaluation of some new 4-aminoquinoline derivatives

Medicinal Chemistry Research

Volumn 22, Issue 8, 2013, Pages 3703-3711

  Rudrapal, Mithun ^a   Chetia, Dipak ^a   Prakash, Anil ^b  

^a DIBRUGARH UNIVERSITY   (India)

^b REGIONAL MEDICAL RESEARCH CENTRE   (India)

Author keywords

7 Chloro 4 aminoquinoline; Antibacterial; Antimalarial; Aromatic bulky substituent; Lipophilicity

Indexed keywords

3 (3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL) 2 (2 FLUOROPHENYL) 1,3 THIAZINAN 4 ONE; 3 (3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL) 2 (2 FURYL) 1,3 THIAZINAN 4 ONE; 3 (3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL) 2 (3 HYDROXYPHENYL) 1,3 THIAZINAN 4 ONE; 3 (3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL) 2 (4 (DIMETHYLAMINO)PHENYL) 1,3 THIAZINAN 4 ONE; 3 (3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL) 2 (4 METHOXYPHENYL) 1,3 THIAZINAN 4 ONE; 3 (3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL) 2 (5 METHYLTHIOPHEN 2 YL) 1,3 THIAZINAN 4 ONE; 3 (3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL) 2 ETHYL 1,3 THIAZINAN 4 ONE; 4 AMINOQUINOLINE DERIVATIVE; ANTIBIOTIC AGENT; ANTIMALARIAL AGENT; CHLOROQUINE; OFLOXACIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIMALARIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACILLUS SUBTILIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; LIPOPHILICITY; MASS SPECTROMETRY; NONHUMAN; PLASMODIUM FALCIPARUM; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84879501690     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0371-9     Document Type: Article

References (26)

1. Casteel DA (2003) Antimalarial agents. In: Abraham DJ (ed) Burger's medicinal chemistry and drug discovery, 5th edn. Wiley Interscience, New York, p 920
2. Chiang PK, Bujnicki JM, Su S, Lanar DE (2006) Malaria: therapy genes and vaccines. Curr Mol Med 6(3):309
3. Chou AC, Chevli R, Fitch CD (1980) Ferriprotoporphyrin IX fulfills the criteria for identification as the chloroquine receptor of malaria parasites. Biochemistry 19:1543-1549
4. Collee JG, Duguid JP, Fraser MG, Marmion BP, McCartney M (1989) Practical medical microbiology, 13th edn. Churchill Livingstone, London
5. Dorn A, Stoffel R, Matile H, Bubendorf A, Ridley RG (1995) Malarial hemozoin/β-hematin supports haem polymerization in the absence of protein. Nature 374:269-271
6. Egan TJ, Marques HM (1999) The role of haem in the activity of chloroquine and related antimalarial drugs. Coord Chem Rev 190-192:493-517
7. Farooq U, Mahajan RC (2004) Drug resistance in malaria. J Vector Borne Dis 41:45
8. Foley M, Tilley L (1998) Quinoline antimalarials: mechanism of action and resistance and prospects for new agents. Pharmacol Ther 79(1):60-67
9. Gillies HM (2000) Management of severe malaria: a practical handbook, 2nd edn. WHO, Geneva
10. Goker H, Kus C, Boykin DW, Yildiz S, Altanlar N (2002) Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species. Bioorg Med Chem 10:2589-2596
11. He Y, Wu B, Yang J, Robinson D, Risen L, Ranken R, Blyh L, Sheng S, Swayze EE (2003) 2-Piperidin-4-yl-benzimidazoles with broad spectrum antibacterial activities. Bioorg Med Chem Lett 13:3253-3256
12. Hewitt W (2004) Microbiological assay for pharmaceutical analysis: a rational approach. Interpharm/CRC, New York
13. Lambros C, Vanderberg JPJ (1979) Synchronization of Plasmodium falciparum erythrocytic stages in culture. Parasitology 65:418-420
14. Madrid PB, Wilson NT, DeRisi JL, Guy RK (2004) Parallel synthesis and antimalarial screening of a 4-aminoquinoline library. J Comb Chem 6:437-442
15. Pandey AV, Bisht H, Babbarwal VK, Srivastava J, Pandey KC, Chauhan VS (2001) Mechanism of malarial haem detoxification inhibition by chloroquine. Biochem J 355:333-338
16. Ridley R (2002) Medical need, scientific opportunity and the drive for antimalarial drugs. Nature 415:686-693
17. Silverstein RM, Webster FX (2005) Spectrometric identification of organic compounds, 6th edn. Wiley, New York
18. Solomon VR, Haq W, Srivastava K, Puri SK, Katti SB (2005) Design and synthesis of new antimalarial agents from 4-aminoquinoline. Bioorg Med Chem 13:2157-2165
19. Solomon VR, Puri SK, Srivastava K, Katti SB (2007) Synthesis and antimalarial activity of side chain modified 4-aminoquinoline derivatives. J Med Chem 50:394-398
20. Sullivan DJ, Gluzman IY, Russell DG, Goldberg DE (1996) On the molecular mechanism of chloroquine's antimalarial action. Proc Natl Acad Sci USA 93:11865-11870
21. Talisuna AO, Loland P, Alessandro UD (2004) History, dynamics, and public health importance of malaria parasite resistance. Clin Microbiol Rev 17(1):236
22. Tilley L, Loria P, Foley M (2001) Chloroquine and Other Quinoline Antimalarials. In: Rosenthal PJ (ed.) Antimalarial Chemotherapy: mechanisms of action, resistance, and new directions in drug discovery. Humana, New Jersey, pp 89-99, pp 103-105
23. Trager W, Jensen JB (1976) Human malaria parasites in continuous culture. Science 193:673-675
24. White WJ (2008) Plasmodium knowlesi: the fifth human malaria parasite. Clin Infect Dis 46:172
25. Wiesner J, Ortmann R, Schlitzer M (2003) New antimalarial drugs. Angew Chem Int Ed Engl 42:5274
26. World Health Organization (1998) http://www.rbm.who.int/ what is malaria? Roll back malaria. World Health Organization, Geneva. Accessed 25 April 2009