Concise synthesis of 5,6-dihydrovaltrate leading to enhanced Rev-export inhibitory congener.
Bioorg Med Chem
; 18(16): 5975-80, 2010 Aug 15.
Article
in En
| MEDLINE
| ID: mdl-20643553
ABSTRACT
The concise synthesis of 5,6-dihydrovaltrate (2), the bioisostere of valtrate (1) showing anti-HIV activity by inhibition for nuclear export of Rev, has been achieved from the commercially available iridoid genipin (3). Analysis of steric influence of the substituents linked to the three hydroxyl groups was conducted by the synthesized three analogs (2a-2c). Consequently, attenuation of steric hindrance around the epoxy portion was revealed to enhance inhibitory potency for Rev-export. In addition to this finding, 1-acetoxy analog 2b was disclosed as the promising Rev-export inhibitor superior to 1.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
HIV Infections
/
HIV-1
/
Anti-HIV Agents
/
Iridoids
/
Rev Gene Products, Human Immunodeficiency Virus
Limits:
Humans
Language:
En
Journal:
Bioorg Med Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2010
Document type:
Article
Affiliation country: