Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib.
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).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...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.
Spencer
John
J
School of Science, University of Greenwich at Medway, Central Avenue, Chatham, Kent ME4 4TB, England.
Chowdhry
Babur Z
BZ
Hamid
Samiyah
S
Mendham
Andrew P
AP
Male
Louise
L
Coles
Simon J
SJ
Hursthouse
Michael B
MB
D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors*; D011758:Pyrroles / Q000737:chemistry*; D000077210:Sunitinib
D007211:Indoles; D011758:Pyrroles; D011505:Protein-Tyrosine Kinases; D000077210:Sunitinib