Preparation of the enantiomers of the analgesic E-3710.

Hueso-Rodríguez, Juan A.; Berrocal, Joana; Gutierrez, B.; Farré, A.J.; Frigola, Jordi

doi:10.1016/s0960-894x(01)80890-8

Cited by 18 publications

(7 citation statements)

References 15 publications

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“…19 All 1 H NMR measurements were carried out on a Varian UNITY 300 spectrometer, operating at 300 MHz. 19 All 1 H NMR measurements were carried out on a Varian UNITY 300 spectrometer, operating at 300 MHz.…”

Section: Methodsmentioning

confidence: 99%

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

1999

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The use of four cyclodextrins (three native and one ␤-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 ␤-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.

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Section: Methodsmentioning

confidence: 99%

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

1999

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“…[36] Others, such as 3-benzoylpyrazoles, can act as precursors of other important heterocyclic compounds (e.g., in the preparation of Cizolirtine, a potent analgesic). [37,38] This highlights the potential applications of benzoylpyrazole derivatives and has stimulated the study of their synthesis. With these possible applications and our previous work on the synthesis of pyrazoles from chromone precursors in mind, [31,32] a program aiming at the preparation of novel benzoylpyrazole derivatives from 3-AFs has been set up.…”

Section: Introductionmentioning

confidence: 98%

3-Aroyl-5-hydroxyflavones: Synthesis and Transformation into Aroylpyrazoles

et al. 2002

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“…Thus compound 408, an analogue of vitamin D, has been prepared [384]. Others, like 409, a CNS agent, have been obtained by resolution [385]. Pyrazoles substituted at position 3 by (2R)-bornane-10,2-sultam 410 have been described and their annular tautomerism determined by X-ray and NMR spectroscopy [386].…”

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confidence: 99%