Fast and selective synthesis of novel cyclic sulfamide HIV-1 protease inhibitors under controlled microwave heating

Tetrahedron

Volumn 62, Issue 19, 2006, Pages 4671-4675

  Gold, Henrik ^a   Ax, Anna ^a   Vrang, Lotta ^b   Samuelsson, Bertil ^b   Karlén, Anders ^a   Hallberg, Anders ^a   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b MEDIVIR AB   (Sweden)

Author keywords

Aminocarbonylation; Goldberg; HIV 1 protease inhibitor; Microwave

Indexed keywords

3,4,5,6 TETRAHYDRO 2 (2 BENZAMIDOBENZYL) 7 BENZYL 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2 (2 PHENYLACETAMIDOBENZYL) 7 BENZYL 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2 (N BENZYL 2 AMIDOBENZYL) 7 BENZYL 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2 (N PHENYL 2 AMIDOBENZYL) 7 BENZYL 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2 [2 (3 METHOXYPHENYLACETAMIDO)BENZYL] 7 BENZYL 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2 [2 [2 (2 NAPHTHYL)ACETAMIDO]BENZYL] 7 BENZYL 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2,7 BIS(2 BENZAMIDOBENZYL) 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2,7 BIS(N BENZYL 2 AMIDOBENZYL) 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2,7 BIS(N PHENYL 2 AMIDOBENZYL) 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2,7 BIS[(2 PHENYLACETAMIDO)BENZYL] 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2,7 BIS[2 [2 (2 NAPHTHYL)ACETAMIDO]BENZYL] 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; 3,4,5,6 TETRAHYDRO 2,7 BIS[2 [2 (3 METHOXYPHENYL)ACETAMIDO]BENZYL] 4,5 DIHYDROXY 1,2,7 THIADIAZEPINE 1,1 DIOXIDE; PALLADIUM; PROTEINASE INHIBITOR; SILVER; SULFAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; ARYLATION; BENZYLATION; CARBONYLATION; CATALYSIS; CATALYST; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS 1; MICROWAVE COOKING; PRIORITY JOURNAL; RELIABILITY;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 33645969594     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.094     Document Type: Article

References (17)

1. Lidström P., Tierney J., Wathey B., and Westman J. Tetrahedron 57 (2001) 9225-9283
2. Larhed M., Moberg C., and Hallberg A. Acc. Chem. Res. 35 (2002) 717-727
3. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
4. Lew A., Krutzik P.O., Hart M.E., and Chamberlin A.R. J. Comb. Chem. 4 (2002) 95-105
5. Bremberg U., Larhed M., Moberg C., and Hallberg A. J. Org. Chem. 64 (1999) 1082-1083
6. Nilsson P., Gold H., Larhed M., and Hallberg A. Synthesis (2002) 1611-1614
7. Morimoto T., and Kakiuchi K. Angew. Chem., Int. Ed. 43 (2004) 5580-5588
8. Yin J.J., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 6043-6048
9. Lam P.Y.S., Jadhav P.K., Eyermann C.J., Hodge C.N., Ru Y., Bacheler L.T., Meek O.M.J., and Rayner M.M. Science 263 (1994) 380-384
10. Bäckbro K., Löwgren S., Öesterlund K., Atepo J., Unge T., Hultén J., Bonham N.M., Schaal W., Karlén A., and Hallberg A. J. Med. Chem. 40 (1997) 898-902
11. Schaal W., Karlsson A., Ahlsen G., Lindberg J., Andersson H.O., Danielson U.H., Classon B., Unge T., Samuelsson B., Hulten J., Hallberg A., and Karlen A. J. Med. Chem. 44 (2001) 155-169
12. Ax A., Schaal W., Vrang L., Samuelsson B., Hallberg A., and Karlen A. Bioorg. Med. Chem. 13 (2005) 755-764
13. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., and Ferrin T.E. J. Comput. Chem. 25 (2004) 1605
14. Wannberg J., and Larhed M. J. Comb. Chem. 68 (2003) 5750-5753
15. Bouzide A., and Sauve G. Tetrahedron Lett. 38 (1997) 5945-5948
16. Danielson H., Lindgren M.T., Markgren P.O., and Nillroth U. Adv. Exp. Med. Biol. 436 (1998) 99-103
17. Nillroth U., Vrang L., Markgren P.-O., Hultén J., Hallberg A., and Danielson U.H. Antimicrob. Agents Chemother. 41 (1997) 2383-2388