2-Carbethoxy-4-(4-bromophenyl)-1-methylpyrrole | 127572-53-6

• 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-Carbethoxy-4-(4-bromophenyl)-1-methylpyrrole
• 英文别名: Ethyl 4-(4-bromophenyl)-1-methylpyrrole-2-carboxylate
• CAS: 127572-53-6
• 化学式: C₁₄H₁₄BrNO₂
• 分子量: 308.175
• InChiKey: DLZVRLKMBKBDJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Carbethoxy-4-(4-bromophenyl)-1-methylpyrrole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以85%的产率得到2,4-dibromo-5-carbethoxy-3-(4-bromophenyl)-1-methylpyrrole
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 2,4-Disubstituted and 2,3,4-Trisubstituted Brominated Pyrroles in Murine and Human Cultured Tumor Cells

  摘要：

  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.

  DOI：

  10.1002/(sici)1521-4184(200001)333:1<3::aid-ardp3>3.0.co;2-4
• 作为产物：
  描述：

  肌氨酸乙酯盐酸盐 、 N-(2-(4-bromophenyl)-3-(dimethylamino)allylidene)-N-methylmethanaminium perchlorate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以78%的产率得到2-Carbethoxy-4-(4-bromophenyl)-1-methylpyrrole
  参考文献：
  名称：

  Application of 2-substituted vinamidinium salts to the synthesis of 2,4-disubstituted pyrroles

  摘要：

  DOI：

  10.1021/jo00302a047

文献信息

• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS AND METHODS
  申请人：Qian Xiangping

  公开号：US20130096315A1

  公开（公告）日：2013-04-18

  Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of one or more mitotic kinesins are disclosed.

  本文披露了一种通过调节一个或多个有丝分裂动力蛋白的活性来治疗细胞增殖性疾病和障碍的化合物。
• GUPTON, JOHN T.;KROLIKOWSKI, DALE A.;YU, RICHARD H.;RIESINGER, STEVE W.;S+, J. ORG. CHEM., 55,(1990) N5, C. 4735-4740
  作者：GUPTON, JOHN T.、KROLIKOWSKI, DALE A.、YU, RICHARD H.、RIESINGER, STEVE W.、S+

  DOI：——

  日期：——
• US8772507B2
  申请人：——

  公开号：US8772507B2

  公开（公告）日：2014-07-08
• Application of 2-substituted vinamidinium salts to the synthesis of 2,4-disubstituted pyrroles
  作者：John T. Gupton、Dale A. Krolikowski、Richard H. Yu、Steve W. Riesinger、James A. Sikorski

  DOI：10.1021/jo00302a047

  日期：1990.7
• 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.