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Musso, D.L. et al.

Musso, Cochran, Kelley, McLean, Selph, Rigdon, Orr, Davis, Cooper, Styles, Thompson, Hall,

Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity.

The design of rigid cyclic analogues derived from cinnamamide 1, (E)-N-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide, and beta-methylcinnamamide 2, (E)-N-cyclopropyl-3-(3-fluorophenyl)but-2-enamide, has led to the discovery of the potent, centrally acting muscle relaxant (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 17. Compound 17 also possesses potent antiinflammatory and analgesic activity. This paper describes the synthesis and the muscle relaxant, antiinflammatory, and analgesic structure-activity relationships of 17 and 67 of its analogues. Compound 17 has been taken into phase I clinical trials.[1]

References

Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity. Musso, D.L., Cochran, F.R., Kelley, J.L., McLean, E.W., Selph, J.L., Rigdon, G.C., Orr, G.F., Davis, R.G., Cooper, B.R., Styles, V.L., Thompson, J.B., Hall, W.R. J. Med. Chem. (2003) [Pubmed]

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