2-(1'-Hydroxyethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione | 215371-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1'-Hydroxyethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione
• 英文别名: Benzo[1,4-b']dithiophene-4,8-dione, 2-(1-hydroxyethyl)-；2-(1-hydroxyethyl)thieno[3,2-f][1]benzothiole-4,8-dione
• CAS: 215371-63-4
• 化学式: C₁₂H₈O₃S₂
• 分子量: 264.326
• InChiKey: ICOJWFLYZGAGHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  493.5±45.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1'-Hydroxyethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione 以68%的产率得到2-(1'-Acetoxyethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione
  参考文献：
  名称：

  Naphtho- and dihydrobenzo-thiophene derivatives as cytotoxic antitumor agents

  摘要：

  作为细胞毒性剂有用的化合物是从以下化合物组中选择的：公式I的化合物和公式II的化合物： 其中：R1、R2、R3和R4分别独立地选择自以下组合物：氢、烷基、羧基、烷氧基、羟基烷基、烷基羰基、烷基羰氧基、烷基取代的烷基羰氧基、硫代苯基羰基、硝基和氰基；硫代苯基和硫代苯基硫代苯基，每种可能未取代或取代为烷基、羧基、烷氧基、羟基烷基、烷基羰基、烷基羰氧基、烷基取代的烷基羰氧基、硝基或氰基；但至少其中一个R1、R2、R3和R4不是氢；A1和A2分别选择自以下组合物：═O、烷基、烷氧基和烷基羰氧基；及其药用可接受的盐。当A1和A2为═O时，中心环只有两个，而不是三个，双键。

  公开号：

  US06174913B1
• 作为产物：
  描述：

  4-acetoxy-2-acetylbenzo<1,2-b:5,4-b'>dithiophene 在 chromium(VI) oxide 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-(1'-Hydroxyethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 2-Acetyl-4,8-dihydrobenzodithiophene-4,8-dione Derivatives

  摘要：

  2-Acetyl-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (9) and 2-acetyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione (19), together with 10 related mono- and disubstituted derivatives, were synthesized and evaluated in vitro by NCI against eight cancer types. All compounds showed significant activity against melanoma, HL-60 leukemia, NCI-H23 non-small-cell lung cancer, OVCAR-3 ovarian cancer, and MDA-MB-435 and MDA-N breast cancer cell lines. Compound 11, 2-(1'-acetoxyethyl)-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione, showed the highest overall potency (mean GI(50) = 40 nM).

  DOI：

  10.1021/jm980394t

文献信息

• 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。
• 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.
• NAPHTHO- AND DIHYDROBENZO-THIOPHENE DERIVATIVES AS CYTOTOXIC ANTITUMOR AGENTS
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：EP1093456A2

  公开（公告）日：2001-04-25
• US6174913B1
  申请人：——

  公开号：US6174913B1

  公开（公告）日：2001-01-16
• US6337346B1
  申请人：——

  公开号：US6337346B1

  公开（公告）日：2002-01-08