铜酸盐(4-),[2-[2-[[2-[3-[[4-氯-6-[乙基[4-[[2-(硫代氧代)乙基]磺酰]苯基]氨基]-1,3,5-三嗪-2-基]氨基]-2-(羟基-kO)-5-硫代苯基]二氮烯基-kN2]苯基甲基]二氮烯基-kN1]-4-硫代苯酸根(6-)-kO]-,(1:4)氢,(SP-4-3)- | 391219-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 铜酸盐(4-),[2-[2-[[2-[3-[[4-氯-6-[乙基[4-[[2-(硫代氧代)乙基]磺酰]苯基]氨基]-1,3,5-三嗪-2-基]氨基]-2-(羟基-kO)-5-硫代苯基]二氮烯基-kN2]苯基甲基]二氮烯基-kN1]-4-硫代苯酸根(6-)-kO]-,(1:4)氢,(SP-4-3)-
• 英文名称: (3,5-dichlorophenyl)benzothiazole
• 英文别名: 2-(3,5-Dichlorophenyl)benzo[d]thiazole；2-(3,5-dichlorophenyl)-1,3-benzothiazole
• CAS: 391219-75-3
• 化学式: C₁₃H₇Cl₂NS
• 分子量: 280.177
• InChiKey: BHDPHVYUAGNQFV-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C
• 沸点：
  427.1±55.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-[(3,5-dichlorophenyl)methyl]-2-iodoaniline 在 potassium sulfide 、 四甲基乙二胺 、 copper(I) bromide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 以65%的产率得到铜酸盐(4-),[2-[2-[[2-[3-[[4-氯-6-[乙基[4-[[2-(硫代氧代)乙基]磺酰]苯基]氨基]-1,3,5-三嗪-2-基]氨基]-2-(羟基-kO)-5-硫代苯基]二氮烯基-kN2]苯基甲基]二氮烯基-kN1]-4-硫代苯酸根(6-)-kO]-,(1:4)氢,(SP-4-3)-
  参考文献：
  名称：

  Copper-Catalyzed Double C–S Bonds Formation via Different Paths: Synthesis of Benzothiazoles from N-Benzyl-2-iodoaniline and Potassium Sulfide

  摘要：

  A new, highly efficient procedure for the synthesis of benzothiazoles from easily available N-benzyl-2-iodoaniline and potassium sulfide has been developed. The results show copper-catalyzed double C-S bond formation via a traditional cross-coupling reaction and an oxidative cross-coupling reaction.

  DOI：

  10.1021/ol403638d

文献信息

• Solid phase combinatorial synthesis of benzothiazoles and evaluation of topoisomerase II inhibitory activity
  作者：Suk-June Choi、Hyen Joo Park、Sang Kook Lee、Sang Woong Kim、Gyoonhee Han、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2005.09.051

  日期：2006.2

  To investigate one possible mechanism of action of the cytotoxic activity of benzothiazoles, we synthesized 2-(substituted-phenyl)benzothiazoles and evaluated their ability to inhibit topoisomerase 11 activities. Solid phase combinatorial method using trityl resin was employed and benzothiazole derivatives with Various substitution on 2'-, 3'-, or 4'-position of phenyl group were obtained in ca. 30 mg scale (7-96% yield). Most of the compounds synthesized exhibited topoisomerase 11 inhibitory activity at 100 mu M. 2-(3-Amino-4-methylphenyl)benzothiazole showed high activity (IC50 = 71.7 mu M), comparable to etoposide (IC50 = 78.4 mu M). (c) 2005 Elsevier Ltd. All rights reserved.