Total synthesis and biological evaluation of clavaminol-G and its analogs.
Eur J Med Chem
; 67: 384-9, 2013 Sep.
Article
in En
| MEDLINE
| ID: mdl-23911578
ABSTRACT
The first total synthesis of clavaminol-G (1) and 1-aminoundecan-2-ol (2) has been achieved from 10-undecenoic acid using epoxidation, regioselective azidolysis and in situ detosylation and reduction reactions as key steps. The methodology is extended for the synthesis of 1-aminoundecan-2-ol derivatives; namely, methyl 11-amino-10-hydroxyundecanoate (3), 11-amino-10-hydroxyundecanoic acid (4) and 11-aminoundecan-1,10-diol (5). Among these, 1-aminoundecan-2-ol (2) exhibited good antimicrobial activity and promising cytotoxicity towards HeLa, MDA-MB-231, MCF-7 and A549 cell lines with IC50 values of 4.36, 4.02, 3.88 and 6.78 µM, respectively. Compound 3 exhibited good activity against HeLa cells (IC50 = 3.59 µM), while compound 5 showed moderate activity towards HeLa and A549 cell lines. Clavaminol G (1) and compound 4 showed no activity towards all the cell lines.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Alkanes
/
Acetamides
/
Anti-Bacterial Agents
/
Antifungal Agents
/
Antineoplastic Agents
Limits:
Humans
Language:
En
Journal:
Eur J Med Chem
Year:
2013
Document type:
Article
Affiliation country:
India