8-Quinolinamines conjugated with amino acids are exhibiting potent blood-schizontocidal antimalarial activities

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 1, 2004, Pages 239-247

  Vangapandu, Suryanarayana ^a,b   Sachdeva, Sandeep ^a   Jain, Meenakshi ^a   Singh, Savita ^a   Singh, Prati Pal ^a   Kaul, Chaman Lal ^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

ALANINE; AMINO ACID DERIVATIVE; ANTIMALARIAL AGENT; LYSINE; N 1 [4 (4 ETHYL 5 HEPTOXY 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2 AMINOPROPANAMIDE; N 1 [4 (4 ETHYL 5 HEPTOXY 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,5 DIAMINOPENTANAMIDE; N 1 [4 (4 ETHYL 5 HEPTOXY 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,6 DIAMINOHEXANAMIDE; N 1 [4 (4 ETHYL 5 HEXOXY 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2 AMINOPROPANAMIDE; N 1 [4 (4 ETHYL 5 HEXOXY 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,5 DIAMINOPENTANAMIDE; N 1 [4 (4 ETHYL 5 HEXOXY 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,6 DIAMINOHEXANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 OCTOXY 8 QUINOLYLAMINO)PENTYL] 2 AMINOPROPANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 OCTOXY 8 QUINOLYLAMINO)PENTYL] 2,5 DIAMINOPENTANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 OCTOXY 8 QUINOLYLAMINO)PENTYL] 2,6 DIAMINOHEXANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 PENTOXY 8 QUINOLYLAMINO)PENTYL] 2 AMINOPROPANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 PENTOXY 8 QUINOLYLAMINO)PENTYL] 2,5 DIAMINOPENTANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 PENTOXY 8 QUINOLYLAMINO)PENTYL] 2,6 DIAMINOHEXANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 PROPOXY 8 QUINOLYLAMINO)PENTYL] 2 AMINOPROPANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 PROPOXY 8 QUINOLYLAMINO)PENTYL] 2,5 DIAMINOPENTANAMIDE; N 1 [4 (4 ETHYL 6 METHOXY 5 PROPOXY 8 QUINOLYLAMINO)PENTYL] 2,6 DIAMINOHEXANAMIDE; N 1 [4 (5 BUTOXY 4 ETHYL 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2 AMINOPROPANAMIDE; N 1 [4 (5 BUTOXY 4 ETHYL 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,5 DIAMINOPENTANAMIDE; N 1 [4 (5 BUTOXY 4 ETHYL 6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,6 DIAMINOHEXANAMIDE; N 1 [4 (6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2 AMINOPROPANAMIDE; N 1 [4 (6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,5 DIAMINOPENTANAMIDE; N 1 [4 (6 METHOXY 8 QUINOLYLAMINO)PENTYL] 2,6 DIAMINOHEXANAMIDE; ORNITHINE; PRIMAQUINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; BLOOD; CONTROLLED STUDY; DRUG CONJUGATION; DRUG POTENCY; DRUG SCREENING; DRUG SENSITIVITY; FEMALE; IN VIVO STUDY; MALARIA; MALE; MOUSE; NONHUMAN; PLASMODIUM BERGHEI; PLASMODIUM YOELII;

PLASMODIUM BERGHEI; PLASMODIUM YOELII NIGERIENSIS;

EID: 0346040398     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.10.028     Document Type: Article

References (22)

1. Rogers D.J., Randolph S.E. Science. 289:2000;1763.
2. World Health Report 1999; World Health Organization: Geneva, Switzerland, 1999.
3. Snow R.W., Craig M.H., Deichman U., LeSueur D. Parasitol. Today. 15:1999;99.
4. Foley M., Tilley L. Int. J. Parasitol. 27:1997;231.
5. Warhurst D.C. J. Pharm. Pharmcol. 49:1997;3.
6. Carson, P. E. In Antimalarial Drugs II; Peters, W., Richards, W. H. G., Eds.; Springer: New York, 1984; p 83.
7. Beutler E., Dern R.J., Alving A.S.J. Lab. Clin. Med. 44:1954;177.
8. Sweeney, T. R. In Antimalarial Drugs II; Peters, W., Richards, W. H. G., Eds.; Springer: Heidelberg, 1984, p 325.
9. Black, R. H.; Canfield, C. J.; Clyde, D. F.; Peters, W.; Wernsdorfer, W. H. In Chemotherapy of Malaria Monograph Series No. 27, revised 2nd ed.; Bruce-Chwatt, L. J., Ed.; WHO: Geneva, 1986, p 102.
10. Peters, W. In Chemotherapy and Drug Resistance in Malaria, 2nd ed.; Academic: London, 1987, p 581.
11. Pirson P., Steiger R.F., Trouet A., Gillet J., Herman F. Ann. Trop. Med. Parasitol. 74:1980;383.
12. Hofsteenge J., Capuano A., Altszuler R., Moore S. J. Med. Chem. 29:1986;1765.
13. Trouet A., Pirson P., Steiger R.F., Masquelier M., Baurain R., Gillet J. Bull. World Health Org. 59:1981;449.
14. Philip A., Kepler J.A., Johnson B.H., Carroll F.I. J. Med. Chem. 31:1988;870.
15. Kar K., Patnaik G.K., Puri S.K., Dutta G.P. Ind. J. Parasitol. 12:1988;259.
16. Baker J.K., Clark A.M., McChesney J.D. J. Pharm. Res. 73:1984;502.
17. Carroll F.I., Berrang B., Linn C.P., Twine C.P. Jr. J. Med. Chem. 22:1979;694.
18. Vangapandu S., Sachedva S., Jain M., Singh S., Singh P.P., Kaul C.L., Jain R. Bioorg. Med. Chem. 11:2003;4557.
19. Hawiger J. Curr. Opin. Chem. Biol. 3:1999;89.
20. Mitchell D.J., Kim D.T., Steinman L., Fathman C.G., Rothbard J.B. J. Pep. Res. 56:2000;318.
21. Garcia-Echeverria C., Ruetz S. Bioorg. Med. Chem. Lett. 13:2003;247.
22. The resolution studies on primaquine (Carroll, F. I.; Berrang, B. Linn, C. P. J. Med. Chem. 1978, 21, 326) indicate that both enantiomers possess similar antimalarial activities, and drug is used clinically as racemate. Thus, in this study, attempts were not made to separate (R, S) and (S, S) diastereoisomers of synthesized 8-quinolinamine conjugates (11-38).