Event Information
Synthetic studies toward biologically active natural products
- Abstract:
Synthetic studies toward two potent anti-tumor agents, brasilibactin A analogue and MPC1001 have been investigated. The hydrophilic brasilibactin A analogue, closely related to the naturally occurring brasilibactin A presented significant cytotoxicity and increased caspase-3 activity, has been synthesized in 32% overall yield from the TBDPS protected cyclic hydroxamic acid. This analogue, containing hydroxamic acid, N-hydroxyformamide, and 2-(2-hydroxyphenyl)-∆2-1,3-oxazoline which can coordinate with metals such as iron and zinc, is a biologically attractive structure due to its improved water solubility. pKa determination and stability constant of iron(III)-brasilibactin A analogue have been studied. MPC1001 was isolated from the microorganism, Cladorrhinum sp. KY4922 and exhibited potent antiproliferative activity (9.3 nM) against a human prostate cancer cell line (DU145). L-serine methyl ester was converted into 1,4-diketopiperazine ring system characteristic of the novel antitumor agent MPC1001. Subsequent trans-diastereoselective aldol addition and 5-endo amidyl radical cyclization have been investigating to generate the bicyclic compound including two representing contiguous rings of MPC1001.
Preliminary Examination Seminar
Student Exams Seminar