Application of multicomponent reactions to antimalarial drug discovery. Part 2: New antiplasmodial and antitrypanosomal 4-aminoquinoline γ- and δ-lactams via a 'catch and release' protocol

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 16, 2006, Pages 5605-5615

  Musonda, Chitalu C ^a   Gut, Jiri ^b   Rosenthal, Philip J ^b   Yardley, Vanessa ^c   Carvalho de Souza, Renata C ^d   Chibale, Kelly ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

^d INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

4 Aminoquinolines; Antimalarial activity; Antitrypanosomal activity; Falcipain 2; Lactams; Multicomponent reaction; Parallel synthesis; Polymer supported reagents; Ugi reaction

Indexed keywords

1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] N CYCLOHEXYL 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] N CYCLOHEXYL 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; 1 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] N CYCLOHEXYL 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; 1 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] N CYCLOHEXYL 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; 1 [4 (7 CHLOROQUINOLIN 4 YLAMINO)BUTYL] N CYCLOHEXYL 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; 1 [4 (7 CHLOROQUINOLIN 4 YLAMINO)BUTYL] N CYCLOHEXYL 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; 1 [6 (7 CHLOROQUINOLIN 4 YLAMINO)HEXYL] N CYCLOHEXYL 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; 1 [6 (7 CHLOROQUINOLIN 4 YLAMINO)HEXYL] N CYCLOHEXYL 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; ANTIMALARIAL AGENT; ANTITRYPANOSOMAL AGENT; FALCIPAIN 2; LACTAM DERIVATIVE; N TERT BUTYL 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; N TERT BUTYL 1 [2 (7 CHLOROQUINOLIN 4 YLAMINO)ETHYL] 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; N TERT BUTYL 1 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; N TERT BUTYL 1 [3 (7 CHLOROQUINOLIN 4 YLAMINO)PROPYL] 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; N TERT BUTYL 1 [4 (7 CHLOROQUINOLIN 4 YLAMINO)BUTYL] 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; N TERT BUTYL 1 [4 (7 CHLOROQUINOLIN 4 YLAMINO)BUTYL] 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; N TERT BUTYL 1 [6 (7 CHLOROQUINOLIN 4 YLAMINO)HEXYL] 2 METHYL 5 OXOPYRROLIDINE 2 CARBOXAMIDE; N TERT BUTYL 1 [6 (7 CHLOROQUINOLIN 4 YLAMINO)HEXYL] 2 METHYL 6 OXOPIPERIDINE 2 CARBOXAMIDE; NITROGEN; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; CELL STRAIN KB; CHEMICAL REACTION; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; NONHUMAN; PLASMODIUM FALCIPARUM; PURIFICATION; TRYPANOSOMA BRUCEI;

AMINOQUINOLINES; ANIMALS; ANTIMALARIALS; CELL LINE; HUMANS; LACTAMS; PARASITIC SENSITIVITY TESTS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA BRUCEI RHODESIENSE;

PLASMODIUM FALCIPARUM; TRYPANOSOMA BRUCEI;

EID: 33745585548     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.04.035     Document Type: Article

References (35)

1. Domling A. Curr. Opin. Chem. Biol. 6 (2002) 303-313
2. Gallop M.A., Barret R.W., Dower W.J., Fodor S.P., and Gordon E.M. J. Med. Chem. 37 (1994) 1233-1251
3. Golisade A., Wiesner J., Herforth C., Joma H., and Link A. Bioorg. Med. Chem. 10 (2002) 769-777
4. Teague S.J., Davis A.M., Leeson P.D., and Oprea T. Angew. Chem., Int. Ed. 38 (1999) 3743-3748
5. Armstrong R.W., Combs A.P., Tempest P.A., Brown S.D., and Keating T.A. Acc. Chem. Res. 29 (1996) 123-131
6. Orru R.V.A., and de Greef M. Synthesis (2003) 1471-1499
7. Hulme C., and Gore V. Curr. Med. Chem. 10 (2003) 51-80
8. Ugi I. Angew. Chem., Int. Ed. Engl. 1 (1962) 8-21
9. Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3168-3210
10. Musonda C.C., Taylor D., Lehman J., Gut J., Rosenthal P.J., and Chibale K. Bioorg. Med Chem. Lett. 14 (2004) 3901-3905
11. Nixey T., Kelly M., and Hulme K. Tetrahedron Lett. 41 (2000) 8729-8733
12. Hulme C., Morrissette M.M., Volz F.A., and Burns C.J. Tetrahedron Lett. 39 (1998) 1113-1116
13. Keating T.A., and Armstrong R.W. J. Org. Chem. 61 (1996) 8935-8939
14. Kim Y.B., Choi E.H., Keum G., Kang S.B., Lee D.H., Koh H.Y., and Kim Y. Org. Lett. 3 (2001) 4149-4152
15. Gedey S., van der Eycken J., and Fullop F. Org. Lett. 4 (2002) 1967-1969
16. Kolb J., Beck B., and Domling A. Tetrahedron Lett. 43 (2002) 6897-6901
17. Short K.M., Ching B.W., and Mjalli A.M.M. Tetrahedron 53 (1997) 6653-6679
18. Li Z., Yeo S.L., Pallen C.J., and Ganesan A. Bioorg. Med. Chem. Lett. 8 (1998) 2443-2446
19. Sutherlin D.P., Stark T.M., Hughes R., and Armstrong W.R. J. Org. Chem. 61 (1996) 8350-8354
20. Portlock D., Naskar D., West L., Ostaszewski R., and Chen J.J. Tetrahedron Lett. 44 (2003) 5121-5124
21. Veber D.F., Johnson S.R., Cheng H.Y., Smith B.R., Ward K.W., and Kopple K.D. J. Med. Chem. 45 (2002) 2615-2623
22. De D., Byers B.L., and Krogstad D.J. J. Heterocycl. Chem. 34 (1997) 315-320
23. Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., and Taylor S.J. J. Chem. Soc., Perkin Trans. 1 (2000) 3815-4196
24. Kirschling A., Monenshchein H., and Wittenburg R. Angew. Chem., Int. Ed. 40 (2001) 650-679
25. Tzschucke C.C., Markert C., Bannwarth W., Roller S., Hebel R., and Haag R. Angew. Chem., Int. Ed. 41 (2002) 3964-4000
26. Stromeier G.A., and Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 621-624
27. Siegel M.G., Hahn P.J., Dressman B.A., Fritz J.F., Grunwell J.R., and Kaldor S. Tetrahedron Lett. 38 (1997) 3357-3360
28. Madrid P., Wilson N.T., DeRisi J.L., and Guy R.K. J. Comb. Chem. 6 (2004) 437-442
29. Madrid P., Sherrill J., Liou A.P., Weisman J.L., DeRisi J.L., and Guy R.K. Bioorg. Med. Chem. Lett. 15 (2005) 1015-1018
30. O'Neill P.M., Willock D.J., Hawley S.R., Bray P.G., Storr R.C., Ward S.A., and Park B.K. J. Med. Chem. 40 (1997) 437-448
31. De D., Krogstad F.M., Byers L.D., and Krogstad D.J. J. Med. Chem. 41 (1998) 4918-4926
32. Kaschula C.H., Egan T.J., Hunter R., Basilica N., Parapini S., Taramelli D., Pasini E., and Monti D. J. Med. Chem. 45 (2002) 3531-3539
33. Powers J.C., Asgian J.L., Ekici O.D., and James K.E. Chem. Rev. 102 (2002) 4639-4750
34. Greenbaum D.C., Mackey Z., Hansell E., Doyle P., Gut J., Caffrey C.R., Lehman J., Rosenthal P.J., McKerrow J.H., and Chibale K. J. Med. Chem. 47 (2004) 3212-3219
35. Raz B., Iten M., Grether-Buhler Y., Kaminsky R., and Brun R. Acta Trop. 68 (1997) 139-147