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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.44B [2005] >
IJC-B Vol.44B(03) [March 2005] >
| Title: | Importance of sulfoxidation in rapid racemisation of glitazones |
| Authors: | Ahmed, Majid
Khanna, Smriti
Bharatam, Prasad V |
| Issue Date: | Mar-2005 |
| Publisher: | CSIR |
| IPC Code: | Int.Cl.7 C 07 D 283/02 |
| Abstract: | AM1 calculations on equilibrium and transition state geometries of keto
and enol forms of glitazones were carried out and compared with those of some
carbonyl compounds. The results show that the energy requirements for
enolisation of glitazones are much higher than the standard carbonyl systems.
Neither the ring system, nor the additional functional groups in thiazolidinedione
terminal ring facilitate the keto-enol tautomerisation, hence keto-enol
tautomerisation cannot be considered as the cause for rapid racemisation in
glitazones. Thio compounds are known to undergo reversible oxidation and the
barrier for 1, 3-H shift in S-oxide form of thiazolidinediones is significantly
lower than all the other agents studied. This study strongly indicates the
involvement of S-oxidation in the enhanced rate of racemisation of
thiazolidinediones. |
| Page(s): | 600-606 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.44B(03) [March 2005]
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