2,5-bis(1'-hydroxyethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione | 215371-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(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, 2,5-bis(1-hydroxyethyl)-；2,5-bis(1-hydroxyethyl)thieno[3,2-f][1]benzothiole-4,8-dione
• CAS: 215371-66-7
• 化学式: C₁₄H₁₂O₄S₂
• 分子量: 308.379
• InChiKey: SBHSPVCXPBMFDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 2,5-bis(1'-hydroxyethyl)-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione 以68%的产率得到2,5-bis(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；及其药用盐。当A1和A2为═O时，中心环只有两个双键，而不是三个。

  公开号：

  US06337346B1
• 作为产物：
  描述：

  Acetic acid 2,5-diacetyl-benzo[1,2-b;5,4-b']dithiophen-4-yl ester 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 2,5-bis(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

• Naphtho- and dihydrobenzo-thiophene derivatives as cytotoxic antitumor agents
  申请人：University of North Carolina at Chapel Hill

  公开号：US06337346B1

  公开（公告）日：2002-01-08

  Compounds useful as cytotoxic agents are selected from the group consisting of compounds of Formula I and compounds of Formula II: wherein: R1, R2, R3 and R4 are each independently selected from the group consisting of: hydrogen, alkyl, carboxy, alkoxy, hydroxyalkyl, alkylcarbonyl; alkylcarbonyloxy; alkyl substituted with alkylcarbonyloxy, thiophenylcarbonyl; nitro and cyano; thiophenyl and thiophenylthiophenyl, each of which may be unsubstituted or substituted with alkyl, carboxy, alkoxy, hydroxyalkyl, alkylcarbonyl; alkylcarbonyloxy; alkyl substituted with alkylcarbonyloxy, nitro or cyano; subject to the proviso that at least one of R1, R2, R3 and R4 is not hydrogen; A1 and A2 are each selected from the group consisting of: ═O, alkyl, alkoxy, and alkylcarbonyloxy; and the pharmaceutically acceptable salts thereof. When A1 and A2 are ═O, the center ring has only two, and not three, double bonds.

  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；及其药用盐。当A1和A2为═O时，中心环只有两个双键，而不是三个。
• Synthesis and Cytotoxicity of 2-Acetyl-4,8-dihydrobenzodithiophene-4,8-dione Derivatives
  作者：Yu-Hua Chao、Sheng-Chu Kuo、Chun-Hsiung Wu、Chun-Yann Lee、Anthony Mauger、I-Chen Sun、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1021/jm980394t

  日期：1998.11.1

  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).