title: Total synthesis and biological evaluation of clavaminol-G and its analogs.
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.
authors.affiliation: Centre for Lipid Research, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
authors.forename: T
authors.initials: T
authors.lastname: Vijai Kumar Reddy
authors.forename: B L A
authors.initials: BL
authors.lastname: Prabhavathi Devi
authors.forename: R B N
authors.initials: RB
authors.lastname: Prasad
authors.forename: P
authors.initials: P
authors.lastname: Sujitha
authors.forename: C
authors.initials: C
authors.lastname: Ganesh Kumar
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000081:Acetamides; D000473:Alkanes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; C587514:clavaminol-G
keywords: 1-Aminoundecan-2-ol; Antimicrobial activity; Azidolysis; Clavaminol-G; Cytotoxic activity; Epoxidation