4,5-Dihydro-1H-thieno[2,3-g]indole-2,3-dicarboxylic acid dimethyl ester | 158204-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,5-Dihydro-1H-thieno[2,3-g]indole-2,3-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 4,5-dihydro-1H-thieno[2,3-g]indole-2,3-dicarboxylate
• CAS: 158204-83-2
• 化学式: C₁₄H₁₃NO₄S
• 分子量: 291.328
• InChiKey: RQPBDAXRTOXHMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-Dihydro-1H-thieno[2,3-g]indole-2,3-dicarboxylic acid dimethyl ester 在 sodium hydroxide 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.25h， 生成 dimethyl 1-methyl-1H-thieno[2,3-g]indole-2,3-dicarboxylate
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of thiophene analogues of 1-methyl-2,3-bis(hydroxymethyl)benzo[g]indole bis[N-(2-propyl)carbamate]

  摘要：

  The cytotoxicity of the bis[N-(2-propyl)carbamates] 2 and 3 which are linked to thieno[i,j-g]indole scaffolds through methylene bridges were studied as thiopheric analogues of prototype 1. Compounds 2 and 3 were evaluated in vitro against 60 human-tumor cell lines derived from nine cancer-cell types and demonstrated, for compound 3 not only strong growth-inhibitory activities against leukemia cancer cells, but also fairly good activities against the growth of certain renal and ovarian cancer cell lines. Compound 2, the thieno[2,3-g]indole bis-carbamate, possessed only significant (MG-MID log(10) GI(50)= -4.89) and selective cytoxicity against NCI-HOP92 (non-small cell lung), MALME 3M (melanoma) and IGROV 1 (ovarian) cancer cell with log(10) GI(50) values of - 5.66, - 5.48 and - 5.47, respectively. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01201-6
• 作为产物：
  描述：

  反应 6.0h， 以42.5%的产率得到4,5-Dihydro-1H-thieno[2,3-g]indole-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Pinna, Gerard Aime; Pirisi, Maria Antonietta; Paglietti, Giuseppe, Journal of Chemical Research, Miniprint, 1993, # 6, p. 1279 - 1296

  摘要：

  DOI：