Discovery of a Bulky 2-tert-Butyl Group Containing Primaquine Analogue That Exhibits Potent Blood-Schizontocidal Antimalarial Activities and Complete Elimination of Methemoglobin Toxicity

Journal of Medicinal Chemistry

Volumn 47, Issue 2, 2004, Pages 285-287

  Jain, Meenakshi ^a   Vangapandu, Suryanarayana ^a,b   Sachdeva, Sandeep ^a   Singh, Savita ^a   Singh, Prati P ^a   Jena, Gopa B ^a   Tikoo, Kulbhushan ^a   Ramarao, Poduri ^a   Kaul, Chaman L ^a   Jain, Rahul ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 TERT BUTYLPRIMAQUINE; CHLOROQUINE; METHEMOGLOBIN; PRIMAQUINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; MASTOMYS; MORTALITY; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PLASMODIUM YOELII; SCHIZONT; SINGLE DRUG DOSE;

ANIMALS; ANTIMALARIALS; MALARIA; METHEMOGLOBIN; MICE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PLASMODIUM YOELII; PRIMAQUINE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 9144273190     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0304562     Document Type: Article

References (14)

1. Butcher, G. A.; Sinden, R. E.; Curtis, C. Malaria: New Ideas, Old Problems, New Technologies. Parasitol. Today 2000, 16, 43-44.
2. Carson, P. E. In Antimalarial Drugs II; Peters, W., Richards, W. H. G., Eds.; Springer-Verlag: New York, 1984; pp 83-121.
3. LaMontagane, M. P.; Blumbergs, P.; Strube, R. E. 5-(Aryloxy)-4-methylprimaquine Analogues. A Highly Effective Series of Blood and Tissue Schizontocidal Agents. J. Med. Chem. 1982, 25, 1094-1097.
4. Carroll, F. I.; Berrang, B.; Linn, C. P. 4-Substituted 5-[m-(Trifluoromethyl)-phenoxy]primaquine Analogues as Potential Antimalarial Agents. J. Med. Chem. 1985, 28, 1564-1567.
5. LaMontagane, M. P.; Blumberg, P.; Smith, D. C. Antimalarials 16. Synthesis of 2-Substituted Analogues of 8-[(4-Amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3-(trifluoromethyl) -phenoxy]quinoline as Candidate Antimalarials. J. Med. Chem. 1989, 32, 1728-1732.
6. Nodiff, E. A.; Chatterjee, A.; Musallam, H. A. Antimalarial Activities of the 8-Aminoquinolines. Prog. Med. Chem. 1991, 28, 1-40.
7. Fetzner, S.; Tshisuaka, B.; Lingens, F.; Kappl, R.; Hüttermann, J. Bacterial Degradation of Quinoline and Derivatives - Pathways and Their Biocatalyst. Angew. Chem., Int. Ed. Engl. 1998, 37, 576-597.
8. Mirghani, R. A.; Ericsson, O.; Cook, J.; Yu, P.; Gustafsson, L. L. Simultaneous Determination of Quinine and Four Metabolites in Plasma and Urine by High-Performance Liquid Chromatography. J. Chromatogr. B Biomed. Sci. Appl. 2001, 754, 57-64.
9. Pinder, R. M.; Burger, A. Antimalarials II. α-(2-Piperidyl)- and α-(2-pyridyl)-2-trifluoromethyl-4-quinolinemethanols. J. Med. Chem. 1968, 11, 267-269.
10. Schmidt, L. H. Relationship Between Chemical Structure of 8-Aminoquinolines and Their Capabilities for Radical Cure of Infection With Plasmodium Cynomolgi in Rhesus Monkeys. Antimicrob. Agents Chemother. 1983, 24, 615-652.
11. Jain, R.; Vaitilingam, B.; Nayyar, A.; Palde, P. B. Substituted 4-Methylquinolines as a New Class of Anti-Tuberculosis Agents. Bioorg. Med. Chem. Lett. 2003, 13, 1051-1054.
12. Vangapandu, S.; Sachedva, S.; Jain, M.; Singh, S.; Singh, P. P.; Kaul, C. L.; Jain, R. 8-Quinolinamines and Their Pro Prodrug Conjugates as Potent Blood-Schizontocidal Antimalarial Agents. Bioorg. Med. Chem. 2003, 11, 4557-4568.
13. McChesney, J. D. Considerations About the Structure-Activity Relationships of 8-Aminoquinoline Antimalarial Drugs. Bull. World. Health Org. 1981, 59, 459-462.
14. Srivastava, P.; Singh, S.; Jain, G. K.; Puri, S. K.; Pandey, V. C. A simple and Rapid Evaluation of Methemoglobin Toxicity of 8-Aminoquinolines and Related Compounds. Ecotox. Environ. Safety. 2000, 45, 236-239.