Synthesis, Crystal Structure and Antitumor Activity of (E)-1-(7-Methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-3-(2-methoxyphenyl)-2-(1H-1,2,4-triazol-1-yl)propenol

The title compound, (E)-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-3-(2-methoxyphenyl)-2-(1H-1,2,4-triazol-1-yl) propenol (3a), was synthesized by the Aldol condensation reaction of 1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(1,2,4-triazol-1- yl) ethanone with 2-methoxybenzaldehyde and then reduced with NaBH4, and its crystal structure was determined by single-crystal X-ray diffraction: monoclinic system, space group P2(1) with a = 6.2002(3), b = 12.8452(7), c = 13.2257(7) angstrom, Z = 2, V = 1031.23(9) angstrom(3), M-r = 407.46, D-c = 1.312 Mg/m(3), S = 1.054, mu = 0.091 mm(-1), F(000) = 432, the final R = 0.0353 and wR = 0.0769 for 3161 observed reflections (I > 2 sigma(I)). X-ray analysis displays that the title compound adopts an E configuration for the C(7)= C(8) double bond and S configuration for the chirality center with the specific rotation of -63.75 degrees. Furthermore, the stability of the crystal was maintained through the intermolecular hydrogen bond O(1)-H center dot center dot center dot N(3). The antitumor assay exhibits that the title compound 3a (E configuration) has a good antitumor activity against the Hela cell line with the IC50 value of 36.9 mu M, which is better than that of 3b (Z configuration).