Diversity-oriented synthesis of medicinally important 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives and higher analogs.

Abstract

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (Tic) is a constrained analog of phenylalanine (Phe). The Tic unit has been identified as a core structural element present in several peptide-based drugs and forms an integral part of various biologically active compounds. This report covers the biological significance of the Tic core and provides a detailed account of various synthetic approaches available for the construction of Tic derivatives. Along with the traditional methods such as the Pictet-Spengler and Bischler-Nepieralski reactions, we cover various recent approaches such as enyne metathesis, [2 + 2 + 2] cycloaddition and the Diels-Alder reaction to generate Tic derivatives. In addition, syntheses of higher analogs of Tic are also discussed.

• Authors: Sambasivarao Kotha, Deepak Deodhar, Priti Khedkar
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 12 Issue 45 Pg. 9054-91 (Dec 07 2014) ISSN: 1477-0539 [Electronic] England
• PMID: 25299735 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Review)

Chemical References

• Carboxylic Acids

Topics

• Carboxylic Acids (chemical synthesis, chemistry)
• Chemistry, Pharmaceutical