Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib

Spencer, J., Chowdhry, B.Z., Hamid, S., Mendham, A.P., Male, L., Coles, S.J. and Hursthouse, M.B. (2010) Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib. Acta Crystallographica Section C: Structural Chemistry, 66 (2), o71-o78. (doi:10.1107/S0108270109054134).

Abstract

The solid-state structures of a series of seven substituted 3-methylidene-1H-indol-2(3H)-one derivatives have been determined by single-crystal X-ray diffraction and are compared in detail. Six of the structures {(3Z)-3-(1H-pyrrol-2- ylmethylidene)-1H-indol-2(3H)-one, C(13)H(10)N(2)O, (2a); (3Z)-3-( 2-thienylmethylidene)-1H-indol-2(3H)-one, C(13)H(9)NOS, (2b); (3E)-3-(2-furylmethylidene)-1H-indol-2(3H)-one monohydrate, C(13)H(9)NO(2)center dot H(2)O, (3a); 3-(1-methylethylidene)-1H-indol- 2(3H)-one, C(11)H(11)NO, (4a); 3-cyclohexylidene-1H-indol- 2(3H)-one, C(14)H(15)NO, (4c); and spiro[1,3-dioxane-2,3'-indolin]- 2'-one, C(11)H(11)NO(3), (5)} display, as expected, intermolecular hydrogen bonding (N-H center dot center dot center dot O=C) between the 1H-indol-2(3H)-one units. However, methyl 3-(1-methylethylidene)- 2-oxo-2,3-dihydro-1H-indole-1-carboxylate, C(13)H(13)NO(3), (4b), a carbamate analogue of (4a) lacking an N-H bond, displays no intermolecular hydrogen bonding. The structure of (4a) contains three molecules in the asymmetric unit, while (4b) and (4c) both contain two independent molecules.

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Contributors

Author: S.J. Coles

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