Regioselective synthesis of 3-aryl-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic acids as potential insulin receptor activators

Tetrahedron Letters

Volumn 47, Issue 43, 2006, Pages 7579-7582

  Chou, Shan Yen ^a   Chen, Shieh Shung Tom ^a   Chen, Ching Hui ^a   Chang, Lien Shange ^a  

^a DEVELOPMENT CENTER FOR BIOTECHNOLOGY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHOXY 4 ARYLFURAN 2,5 DICARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; FORMIC ACID DERIVATIVE; FURAN DERIVATIVE; INDOLE DERIVATIVE; INSULIN DERIVATIVE; INSULIN RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; DECARBOXYLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 33748904918     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.076     Document Type: Article

References (8)

1. Ross S.A., Gulve E.A., and Wang M. Chem. Rev. 104 (2004) 1255-1282 and references cited therein
2. Liu K., Xu L., Szalkowski D., Li Z., Ding V., Kwei G., Huskey S., Moller D.E., Heck J.V., Zhang B., and Jones A.B. J. Med. Chem. 43 (2000) 3487-3494
3. Chen, S. S.; Zhang, B.; and Li, X. U.S. Patent 6,596,760, 2003.
4. Tse B., and Jones A.B. Tetrahedron Lett. 42 (2001) 6429-6431
5. Johnson D.A. J. Am. Chem. Soc. 75 (1953) 3636-3637
6. Okauchi T., Itonaga M., Minami T., Owa T., Kitoh K., and Yoshino H. Org. Lett. 2 (2000) 1485
7. Notably, the complete removal of superfluous oxalyl chloride before acylation is key to the success of this step, for typical procedure see Supplementary data.
8. Efficacies of compounds on cell-based insulin receptor tyrosine kinase activity will be reported elsewhere.