Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A (1)H NMR study on the solution structures of their host-guest complexes.

Abstract:

:The use of four cyclodextrins (three native and one beta-CD derivative) as NMR chiral solvating agents to resolve the enantiomers of (+/-)-cizolirtine, 1, and its chemical precursor (the carbinol, (+/-)-2), was investigated. The best enantiodiscrimination occurred when beta-cyclodextrin was used. ROESY experiments were performed to qualitatively ascertain the most probable host-guest structures in D(2)O solution, and the binding features found were explained in terms of spatial fitting of the guest molecules into the macrocyclic cavities. No geometrical differences were noted between the two diastereomeric complexes formed by a cyclodextrin and a racemic substrate, so the magnetic nonequivalence induced on guest protons by the enantioselective binding had to be explained as a result of subtle disparities in the orientation and/or the conformational state of the complexed enantiomers.

journal_name

Chirality

journal_title

Chirality

authors

Redondo J,Blázquez MA,Torrens A

doi

10.1002/(SICI)1520-636X(1999)11:9<694::AID-CHIR5>3

subject

Has Abstract

pub_date

1999-01-01 00:00:00

pages

694-700

issue

9

eissn

0899-0042

issn

1520-636X

pii

10.1002/(SICI)1520-636X(1999)11:9<694::AID-CHIR5>3

journal_volume

11

pub_type

杂志文章