Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors.
Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. L-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures of L-chicoric acid 2 were synthesized for the purpose of simplifying the structure of L-chicoric acid. Among synthesized, compounds 2c and 3f showed HIV-1 IN inhibitory activities with IC(50) values of 10.5 and 12.0 microM, respectively, comparable to that of parent compound L-chicoric acid (IC(50)=15.7 microM).
Lee
Seung Uk
SU
Life Sciences Division, Korea Institute of Science & Technology, P.O. Box 131 Cheongryang, Seoul 130-650, Republic of Korea.
Shin
Cha-Gyun
CG
Lee
Chong-Kyo
CK
Lee
Yong Sup
YS
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002109:Caffeic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002396:Catechols / Q000737:chemistry; D015195:Drug Design; D019428:HIV Integrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013386:Succinates / Q000737:chemistry*
D000596:Amino Acids; D002109:Caffeic Acids; D002396:Catechols; D019428:HIV Integrase Inhibitors; D013386:Succinates; C034221:catechol; C100435:chicoric acid