4,5''-dihydroxymethyl-alpha-terthiophene | 185395-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,5''-dihydroxymethyl-alpha-terthiophene
• 英文别名: 5,4"-Dihydroxymethyl-2,2':5', 2"-terthiophene；[5-[5-[4-(hydroxymethyl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]methanol
• CAS: 185395-65-7
• 化学式: C₁₄H₁₂O₂S₃
• 分子量: 308.446
• InChiKey: ZBGPRTXPLWCWSB-UHFFFAOYSA-N

物化性质

• 沸点：
  487.7±40.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5''-dihydroxymethyl-alpha-terthiophene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.0h， 以48%的产率得到4,5''-diformyl-alpha-terthiophene
  参考文献：
  名称：

  Novel protein kinase C inhibitors: synthesis and PKC inhibition of β-substituted polythiophene derivatives

  摘要：

  A series of beta-substituted polythiophene derivatives was synthesized through palladium-catalyzed coupling reaction. Their structure-protein kinase C (PKC) inhibitory activity relationship was studied. The carboxaldehyde and hydroxymethyl derivatives of alpha-terthiophene were potent PKC inhibitors (IC50 = 10(-7) M). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00375-3
• 作为产物：
  描述：

  5-(羟甲基)-[2,2]-联噻吩 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 正丁基锂 、 三丁基氯化锡 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 4,5''-dihydroxymethyl-alpha-terthiophene
  参考文献：
  名称：

  Novel protein kinase C inhibitors: synthesis and PKC inhibition of β-substituted polythiophene derivatives

  摘要：

  A series of beta-substituted polythiophene derivatives was synthesized through palladium-catalyzed coupling reaction. Their structure-protein kinase C (PKC) inhibitory activity relationship was studied. The carboxaldehyde and hydroxymethyl derivatives of alpha-terthiophene were potent PKC inhibitors (IC50 = 10(-7) M). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00375-3

文献信息

• Polythiophene anti-tumor agents
  申请人：Purdue Research Foundation

  公开号：US05741811A1

  公开（公告）日：1998-04-21

  Novel polythiophene compounds useful as anti-tumor agents are described. Preferred compounds of the formula: ##STR1## wherein n is 0-2 and R.sub.2 and R.sub.3 are optionally substituted 2-thienyl or 3-thienyl have been found to exhibit selective cytotoxic activity against transformed human cells. Pharmaceutical compositions containing the described polythiophene compounds are expected to exhibit good chemotherapeutic activity against slow growing tumors based on tumor cell line assays. A method for treating patients having tumors utilizing the disclosed polythiophene compounds is also described.

  本发明涉及一种用作抗肿瘤剂的新型聚噻吩化合物。该化合物的首选式为：##STR1## 其中n为0-2，R.sub.2和R.sub.3为可选取代的2-噻吩基或3-噻吩基，已发现该化合物对转化人类细胞表现出选择性细胞毒性活性。预期含有上述聚噻吩化合物的制药组合物将在基于肿瘤细胞系检测的基础上对慢性生长的肿瘤表现出良好的化学治疗活性。本发明还涉及一种利用上述聚噻吩化合物治疗患有肿瘤的患者的方法。
• US5578636A
  申请人：——

  公开号：US5578636A

  公开（公告）日：1996-11-26
• US5741811A
  申请人：——

  公开号：US5741811A

  公开（公告）日：1998-04-21
• Novel protein kinase C inhibitors: synthesis and PKC inhibition of β-substituted polythiophene derivatives
  作者：Wei-Chu Xu、Qin Zhou、Curtis L. Ashendel、Ching-te Chang、Ching-jer Chang

  DOI：10.1016/s0960-894x(99)00375-3

  日期：1999.8

  A series of beta-substituted polythiophene derivatives was synthesized through palladium-catalyzed coupling reaction. Their structure-protein kinase C (PKC) inhibitory activity relationship was studied. The carboxaldehyde and hydroxymethyl derivatives of alpha-terthiophene were potent PKC inhibitors (IC50 = 10(-7) M). (C) 1999 Elsevier Science Ltd. All rights reserved.