[Synthesis and antiviral activity of hydrazides and substituted benzalhydrazides of betulinic acid and its derivatives].
New nitrogen-containing derivatives of betulinic and betulonic acids, hydrazides and N'-benzalhydrazides, were synthesized. Their antiviral activities toward of influenza A virus, herpes simplex type I virus, enterovirus ECHO6, and HIV-1 were studied in vitro. Betulinic acid 3-oxime was found to have the highest activity against the influenza virus. Betulonic acid, betulinic acid 4-chlorobenzalhydrazide, betulonic acid 3-oxime benzalhydrazide, and betulinic acid hydrazide inhibited the replication of herpes simplex type I virus. Betulinic acid hydrazide also showed antiviral activity toward HIV-1. All the derivatives of betulinic acid under study displayed a low antiviral activity toward enterovirus ECHO6.
Flekhter
O B
OB
Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054 Russia. obf@anrb.ru
Boreko
E I
EI
Nigmatullina
L R
LR
Pavlova
N I
NI
Nikolaeva
S N
SN
Savinova
O V
OV
Eremin
V F
VF
Baltina
L A
LA
Galin
F Z
FZ
Tolstikov
G A
GA
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001671:Biochemistry / Q000379:methods; D002478:Cells, Cultured / Q000821:virology; D002642:Chick Embryo; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004770:Enterovirus / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D009980:Influenza A virus / Q000187:drug effects; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D053978:Pentacyclic Triterpenes; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology; D000094062:Betulinic Acid
D000998:Antiviral Agents; D006834:Hydrazines; D010091:Oximes; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; C478013:betulinic acid 3-oxime; D000094062:Betulinic Acid