4,8-dioxo-4,8-dihydrobenzo-[1,2-b;5,4-b']dithiophene-2-carboxylic acid | 239100-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4,8-dioxo-4,8-dihydrobenzo-[1,2-b;5,4-b']dithiophene-2-carboxylic acid
• 英文别名: Benzo[1,4-b']dithiophene-2-carboxylic acid, 4,8-dioxo-；4,8-dioxothieno[3,2-f][1]benzothiole-2-carboxylic acid
• CAS: 239100-01-7
• 化学式: C₁₁H₄O₄S₂
• 分子量: 264.282
• InChiKey: WTAUYWUADNKEOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  128
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,8-dioxo-4,8-dihydrobenzo-[1,2-b;5,4-b']dithiophene-2-carboxylic acid 在 氨 作用下， 以 水 、 异丙醇 为溶剂， 以82%的产率得到ammonium 4,8-dioxo-4,8-dihydrobenzo-[1,2-b:5,4-b']dithiophene-2-carboxylate
  参考文献：
  名称：

  Novel hydrophilic analogs of 4,8-dihydrobenzodithiophene-4,8-diones as anticancer agents

  摘要：

  本发明公开了4,8-二氢苯并二硫代苯并二酮的亲水衍生物，其作为抗癌药物活性，并包含相同的药物配方。

  公开号：

  US20060069041A1
• 作为产物：
  描述：

  2-Methyl-benzo[1,2-b;5,4-b']dithiophene-4,8-dione 在 chromium(VI) oxide 、 sodium hydroxide 、 硫酸 、 silver nitrate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.5h， 生成 4,8-dioxo-4,8-dihydrobenzo-[1,2-b;5,4-b']dithiophene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Methyl-4,8-dihydrobenzo[1,2-b:5,4-b′]dithiophene-4,8-dione Derivatives

  摘要：

  2- and 3-Methyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione and related derivatives were synthesized and evaluated in vitro by NCI against eight cancer types. Compounds 12-15 showed significant activity against melanoma, NCl-H23 non-small cell lung cancer, and MDA-MB-435 and MDA-N breast cancer cell lines; 2-hydroxymethyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene4,8-dione (13) showed the highest activity against melanoma (mean log GI(50) = -7.74) and the highest overall potency (mean log GI50 = -6.99). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00241-7

文献信息

• Cell differentiation enhancement by hydrophilic derivatives of 4,8-Dihydrobenzo[1,2-b:5,4-b′]dithiophene-4,8-diones in HL-60 leukemia cells
  作者：Yen-Fang Wen、Kuo-Hsiung Lee、Pi-Tsan Huang、Mei-Hwai Chen、Wuu-Chian Shin、Li-Jiau Huang、Mei-Hua Hsu、Chun-Jen Chen、Sheng-Chu Kuo

  DOI：10.1016/j.bmcl.2007.02.044

  日期：2007.5

  Among five carboxamide derivatives (13-17), N-(2-dimethylaminoethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione-2-carboxamide (13) showed the greatest enhancement of all-trans retinoid acid (ATRA)-induced differentiation in HL-60 cells, inducing nearly complete differentiation at a concentration of 0.02 mu M. On the other hand, 2-hydroxymethyl-4,8-dihydrobenzo[1,2b:5,4-b']dithiophene-4,8-dione (2) and 2-(1-hydroxylethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione (18) exhibited excellent and equally potent differentiation effects on HL-60 cells. To improve their water solubility, ester-type hydrophilic prodrugs (23-26) were also synthesized. Compounds 13 and 23-26 are identified in this paper as new anti-leukemic drug candidates. (c) 2007 Published by Elsevier Ltd.
• US7332615B2
  申请人：——

  公开号：US7332615B2

  公开（公告）日：2008-02-19
• Novel hydrophilic analogs of 4,8-dihydrobenzodithiophene-4,8-diones as anticancer agents
  申请人：Huang Pi-Tsan

  公开号：US20060069041A1

  公开（公告）日：2006-03-30

  The present invention discloses hydrophilic derivatives of 4,8-dihydrobenzodithiophene-4,8-diones, which are active as anticancer agents, along with pharmaceutical formulations containing the same.

  本发明公开了4,8-二氢苯并二硫代苯并二酮的亲水衍生物，其作为抗癌药物活性，并包含相同的药物配方。
• Synthesis and Cytotoxicity of Methyl-4,8-dihydrobenzo[1,2-b:5,4-b′]dithiophene-4,8-dione Derivatives
  作者：Yu-Hua Chao、Sheng-Chu Kuo、Kelvin Ku、I-Ping Chiu、Chun-Hsiung Wu、Anthony Mauger、Hui-Kang Wang、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(98)00241-7

  日期：1999.6

  2- and 3-Methyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione and related derivatives were synthesized and evaluated in vitro by NCI against eight cancer types. Compounds 12-15 showed significant activity against melanoma, NCl-H23 non-small cell lung cancer, and MDA-MB-435 and MDA-N breast cancer cell lines; 2-hydroxymethyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene4,8-dione (13) showed the highest activity against melanoma (mean log GI(50) = -7.74) and the highest overall potency (mean log GI50 = -6.99). (C) 1999 Published by Elsevier Science Ltd. All rights reserved.