Novel 3alpha-methoxyserrat-14-en-21beta-ol (PJ-1) and 3beta-methoxyserrat-14-en-21beta-ol (PJ-2)-curcumin, kojic acid, quercetin, and baicalein conjugates as HIV agents.
Sixteen novel compounds; 3alpha-methoxyserrat-14-en-21beta-ol (1) and 3beta-methoxyserrat-14-en-21beta-ol (2) and their curcumin, kojic acid, quercetin, and baicalein conjugates (3)-(18) were designed, synthesized, and evaluated for in vitro anti-HIV-1 reverse transcriptase (RT) activity in infected C8166-CCR5 cells, a human CD4(+) T-lymphocyte cell line. Among them, kojic acid derivatives, 9-12 showed significant biological activity. In particular, the compound 13, the conjugate of two molecules of 3alpha-methoxyserrat-14-en-21beta-ol (1) and one molecule of kojic acid, exerted significant anti-HIV activity with an EC50 value of 0.12microg/mL.
Tanaka
Reiko
R
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@gly.oups.ac.jp
Tsujii
Hiroko
H
Yamada
Takeshi
T
Kajimoto
Tetsuya
T
Amano
Fumio
F
Hasegawa
Junya
J
Hamashima
Yoshio
Y
Node
Manabu
M
Katoh
Kayoko
K
Takebe
Yutaka
Y
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003474:Curcumin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D044950:Flavanones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015658:HIV Infections / Q000188:drug therapy*; D015497:HIV-1 / Q000187:drug effects / Q000201:enzymology*; D006801:Humans; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011794:Quercetin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D012194:RNA-Directed DNA Polymerase / Q000378:metabolism; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013601:T-Lymphocytes / Q000187:drug effects / Q000821:virology; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014764:Viral Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism
C492953:3beta-methoxyserrat-14-en-21beta-ol; D000998:Antiviral Agents; D044950:Flavanones; D011753:Pyrones; D018894:Reverse Transcriptase Inhibitors; D014315:Triterpenes; D014764:Viral Proteins; C006680:baicalein; C011890:kojic acid; D011794:Quercetin; D012194:RNA-Directed DNA Polymerase; D003474:Curcumin