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.
Original language | English |
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Pages (from-to) | 5975-5980 |
Number of pages | 6 |
Journal | Bioorganic and Medicinal Chemistry |
Volume | 18 |
Issue number | 16 |
DOIs | |
Publication status | Published - 2010 Aug 15 |
Keywords
- 5,6-Dihydrovaltrate
- Anti-HIV
- Genipin
- Iridoid
- Rev-export inhibitor
ASJC Scopus subject areas
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry