Title | Design and synthesis of 3,5-disubstituted boron-containing 1,2,4-oxadiazoles as potential combretastatin A-4 (CA-4) analogs. |
Publication Type | Journal Article |
Year of Publication | 2012 |
Authors | Das BC, Tang X-Y, Rogler P, Evans T |
Journal | Tetrahedron Lett |
Volume | 53 |
Issue | 31 |
Pagination | 3947-3950 |
Date Published | 2012 Aug 01 |
ISSN | 0040-4039 |
Abstract | <p>We have designed and synthesized a small library of 3,5-disubstituted-1,2,4-oxadiazole containing combretastatin A-4 (CA-4) analogs. Our objective is to increase the efficacy of the CA-4 as an anti-tubulin and antimitotic agent by substituting the -alkene bond with one of its bioisosteres, the 1,2,4-oxadiazole ring. We also modified the substituents attached to both of the phenyl rings (ring A and B in Fig. 1) of CA-4 for the purpose of diversifying our analogs based on SAR. These compounds were synthesized via a coupling reaction between an amidoxime and a carboxylic acid in DMF solvent, with HOBt as a base, and utilizing EDCI as a coupling reagent. Using this protocol, we synthesized a small library of 10 compounds with moderate to good yields. A detailed biological study is currently undergoing in our laboratory to evaluate the activity of these compounds.</p> |
DOI | 10.1016/j.tetlet.2012.02.110 |
Alternate Journal | Tetrahedron Lett |
PubMed ID | 24039307 |
PubMed Central ID | PMC3771381 |
Grant List | R01 HL056182 / HL / NHLBI NIH HHS / United States R21 AA020630 / AA / NIAAA NIH HHS / United States R37 HL056182 / HL / NHLBI NIH HHS / United States R56 AI093220 / AI / NIAID NIH HHS / United States |