2,4-dibromo-5-carbethoxy-3-(4-bromophenyl)pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,4-dibromo-5-carbethoxy-3-(4-bromophenyl)pyrrole
• 英文别名: JG-05-10；Ethyl 3,5-dibromo-4-(4-bromophenyl)-1H-pyrrole-2-carboxylate
• 化学式: C₁₃H₁₀Br₃NO₂
• 分子量: 451.94
• InChiKey: BLHGOYXIPZHZDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-Carbethoxy-4-(4-bromophenyl)pyrrole 在 pyridinium hydrobromide perbromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,4-dibromo-5-carbethoxy-3-(4-bromophenyl)pyrrole
  参考文献：
  名称：

  Developing novel C-4 analogues of pyrrole-based antitubulin agents: weak but critical hydrogen bonding in the colchicine site

  摘要：

  报告了一系列与 3,5-二溴-4-(3,4-二甲氧基苯基)-1H-吡咯-2-羧酸有关的吡咯化合物的合成、生物学评价和分子建模，对 C-4 取代基进行了评估和优化。微管解聚活性的关键因素似乎是在原本疏水性的子口袋 A 中存在一个位置适当的 Cys241β 受体。

  DOI：

  10.1039/c2md20320k

文献信息

• Synthesis and Cytotoxicity of 2,4-Disubstituted and 2,3,4-Trisubstituted Brominated Pyrroles in Murine and Human Cultured Tumor Cells
  作者：John T. Gupton、Bruce S. Burham、Keith Krumpe、Karen Du、James A. Sikorski、Amy E. Warren、Cheryl R. Barnes、Iris. H. Hall

  DOI：10.1002/(sici)1521-4184(200001)333:1<3::aid-ardp3>3.0.co;2-4

  日期：2000.1

  The 2,4-disubstituted and 2,3,4-trisubstituted brominated pyrroles were successfully prepared and demonstrated potent cytotoxicity against the growth of suspended murine and human tumors, i.e. leukemia and lymphomas, acute monocytic leukemia, and HeLa-S-3 uterine carcinoma. The brominated compounds were more selective in inhibiting the growth of tumors derived from human solid tumors. Nevertheless activity with some of the derivatives occurred in the human KB nasopharynx, SW-480 colon, and HCT ileum adenocarcinoma, and lung A549 carcinoma screens. In Tmolt(4) T cell leukemia cells DNA synthesis was reduced over 60 min from 25 to 100 mu M followed by RNA synthesis reduction. De novo purine synthesis was retarded with the regulatory enzyme PRPP-amino transferase being markedly inhibited with less effects dehydrogenase, dihydrofolate reductase,, nucleoside kinases. After 60 min incubations d[TTP] and d[GTP] pools were marginally reduced. In vitro ct-DNA studies that the agents may affect the DNA molecule itself with DNA viscosity and the Tmolt(4) studies suggest that DNA cross-linking of DNA strands may be present.