Thiaindanones. Thiophene isosteres of indanone

✍ Scribed by Joseph Sam; Alonzo C. Thompson

• Book ID: 102398912
• Publisher: John Wiley and Sons
• Year: 1963
• Tongue: English
• Weight: 327 KB
• Volume: 52
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600520918

✦ Synopsis

The preparation of substituted 4-and 6-thiaindanones' (thiophene isosteres ot indanone) via intramolecular acylatioa of 8-(2-and 3-thien 1)propanoic acids is described. The Wolff-Kishner and sodium borohydride rehctions provided the corresponding thiaindan and thiaindanol (thiophene isosteres of indan and indanol), respectively.

HE IMPORTANCE of molecular size and shape Tin determining biological properties has been recognized for many years. The chemical, physical, and biological properties of isosteres have been studied extensively (2), since they possess steric similarities. Interest in the synthesis and in the biological properties of isosteres is kindled in the hope that useful medicinal agents and essential clues to the mechanism of drug action may be obtained.

Burckhalter and Sam (1) prepared the thiophene isostere (IIIa) of 2-methyl-1-indanone (IV)

but did not report biological activity. Since the thiaindanones (111) represented a ring system that had not been investigated extensively, we were interested in the preparation of other thio-