Meisenheimer rearrangement of azetopyridoindoles. VIII. Synthesis and antiviral activities of 12-carbaeudistomin analogs.
Eudistomins, isolated from the colonial tunicate Eudistoma olivaceum, have been a synthetic target due to their strong antiviral activity against Herpes simplex virus (HSV-1) and activities against certain types of tumors in vivo. In order to examine the structure-activity relationship of eudistomins, 12-carbaeudistomin analogs were synthesized and their activities against influenza A and B virus, HSV-1, HSV-2 and human cytomegalovirus were investigated. Among them, racemic 6-methoxy-12-carbaeudistomin showed similar activity to (-)-debromoeudistomin K, synthesized as a control compound.
Kurihara
T
T
Osaka University of Pharmaceutical Sciences, Japan.
Sakamoto
Y
Y
Kimura
T
T
Ohishi
H
H
Harusawa
S
S
Yoneda
R
R
Suzutani
T
T
Azuma
M
M
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002243:Carbolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D003587:Cytomegalovirus / Q000187:drug effects; D004285:Dogs; D018259:Herpesvirus 1, Human / Q000187:drug effects; D018258:Herpesvirus 2, Human / Q000187:drug effects; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D009980:Influenza A virus / Q000187:drug effects; D009981:Influenza B virus / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
C087387:12-carbaeudistomin; D000998:Antiviral Agents; D002243:Carbolines; D007211:Indoles