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

The title compound, 4-（tert-butyl）-5-（1 H- 1,2,4-triazol- 1 -yl）-N-（2-hydroxy-3,5-diio- dinebenzyl）thiazol-2-amine, was synthesized via the reduction of 4-（tert-butyl）-5-（1H-l,2,4- triazol-l-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） A, Z = 4, V = 2041.66（9） A3, Mr = 599.22, Dc = 1,949 Mg/m3, S = 1.120, p = 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（I） and N（5）-H（5）…O（2）, and an octatomic ring R^（8） is formed via intramolecular hydrogen bond of O（I）-H（IA）…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.

空气氧化法合成丙硫菌唑

以2-(1-氯环丙基)-1-(2-氯苯基)-3-(1,2,4-三唑烷-5-硫酮-1-基)-2-丙醇为原料,在甲基叔丁基醚溶剂中,m(原料)∶v(甲基叔丁基醚)=1∶5,空气作为氧化剂,常温反应6 h,一锅法合成丙硫菌唑,开发出一条操作简便、反应绿色的丙硫菌唑合成工艺,为工业化生产提供了思路。产品经质谱和核磁共振氢谱碳谱确证。

碱催化法合成丙硫菌唑

以2-(1-氯环丙基)-1-(2-氯苯基)-3-(1,2,4-三唑烷-5-硫酮-1-基)-2-丙醇为原料a,氢氧化钠为催化剂,空气为氧化剂,在甲醇中合成丙硫菌唑.其中,原料a∶氢氧化钠=1∶1;甲醇/原料a(V/m)=3;空气过量;反应温度35℃;反应时间4h.反应后处理加盐酸调pH至3,甲苯反萃取、重结晶得到丙硫菌唑,含量≥98%,折百收率≥90%.