2-(3-三氟甲氧基-苯基)-苯并噻唑 | 874739-16-9

• 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: 2-(3-三氟甲氧基-苯基)-苯并噻唑
• 英文名称: 2-(3-(trifluoromethoxy)phenyl)benzo[d]thiazole
• 英文别名: 2-(3-Trifluoromethoxy-phenyl)-benzothiazole；2-[3-(trifluoromethoxy)phenyl]-1,3-benzothiazole
• CAS: 874739-16-9
• 化学式: C₁₄H₈F₃NOS
• 分子量: 295.285
• InChiKey: YFUQRZOMDVSZBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基苯硫醇 、 3-(三氟甲氧基)苯甲酰氯 以13%的产率得到2-(3-三氟甲氧基-苯基)-苯并噻唑
  参考文献：
  名称：

  Solid phase combinatorial synthesis of benzothiazoles and evaluation of topoisomerase II inhibitory activity

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2005.09.051

文献信息

• An efficient desulfitative C–C cross coupling of fused thiazolidine-2-thione with boronic acids and boronic acid pinacol esters: formation of fused thiazoles
  作者：Kandasamy Rajaguru、Arumugam Mariappan、Ramachandran Manjusri、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1039/c5ra17827d

  日期：——

  An efficient Pd(0)-catalyzed Cu(I)-mediated desulfitative C–C cross-coupling of benzo-fused thiazolidine-2-thione with boronic acids under neutral Liebeskind–Srogl conditions is described. The desulfitative cross coupling of boronic acid pinacol esters has also been demonstrated with fused thiazolidine-2-thione under basic conditions to afford fused thiazoles with good to excellent yields.

  描述了在中性Liebeskind-Srogl条件下有效的Pd（0）催化的Cu（I）介导的苯并稠合的噻唑烷-2-硫酮与硼酸的铜（I）介导的脱硫C-C交叉偶联。还已经证明在碱性条件下用稠合的噻唑烷-2-硫酮与硼酸频哪醇酯进行脱硫交叉偶联，从而以良好或极好的收率得到稠合的噻唑。
• 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.