Citation: YE Jiao, XIE Xuan-Qing, LI Kang-Ming, LIU Yong-Chao, SUN Li, HU Ai-Xi. Synthesis, Crystal Structure and Antitumor Activity of 4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)-N-(2-hydroxy-3,5-diiodinebenzyl)-thiazol-2-amine[J]. Chinese Journal of Structural Chemistry, ;2015, 34(3): 344-348. doi: 10.14102/j.cnki.0254-5861.2011-0530 shu

Synthesis, Crystal Structure and Antitumor Activity of 4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)-N-(2-hydroxy-3,5-diiodinebenzyl)-thiazol-2-amine

1.
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China

Corresponding author: YE Jiao, HU Ai-Xi,
Received Date: 9 October 2014
Available Online: 13 November 2014
Fund Project:

The title compound, 4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)-N-(2-hydroxy-3,5-diiodinebenzyl)thiazol-2-amine, was synthesized via the reduction of 4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)-N-benzylidene-thiazol-2-amine with NaBH₄, and its crystal structure was determined by single-crystal X-ray diffraction. The compound crystallizes in monoclinic system, space group P2₁/c with a=7.91944(19), b=10.5250(3), c=24.4985(6)Å, Z=4, V=2041.66(9)Å³, M_r=599.22, D_c=1.949 Mg/m³, S=1.120, μ=3.203 mm^-1, F(000)=1152, the final R=0.0283 and wR=0.0592 for 3490 observed reflections (I>2σ(I)). X-ray analysis displays that the crystal water takes part in three intermolecular hydrogen bonds of O(2)-H(2A)…O(1), O(2)-H(2B)…N(1) and N(5)-H(5)…O(2), and an octatomic ring R₁¹(8) is formed via intramolecular hydrogen bond of O(1)-H(1A)…N(4). Furthermore, the I…I contacts are involved in stabilizing the overall three-dimensional network structure. The preliminary biological test shows the title compound has good antitumor activity with the IC₅₀ value of 26 μM against the Hela cell line.
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