ethyl 3-(p-bromo-benzoyl)-5-(2'-pyridyl)-indolizine-1-carboxylate | 252201-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(p-bromo-benzoyl)-5-(2'-pyridyl)-indolizine-1-carboxylate
• 英文别名: ethyl 3-(4-bromobenzoyl)-5-(pyridin-2-yl)indolizine-1-carboxylate；Ethyl 3-(4-bromobenzoyl)-5-(2-pyridinyl)-1-indolizinecarboxylate；ethyl 3-(4-bromobenzoyl)-5-pyridin-2-ylindolizine-1-carboxylate
• CAS: 252201-20-0
• 化学式: C₂₃H₁₇BrN₂O₃
• 分子量: 449.304
• InChiKey: SKPBPEPJLYXSCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 3-(p-bromo-benzoyl)-5-(2'-pyridyl)-1,2,3,8a-tetrahydroindolizine-1-carboxylate 在 TPCB 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以60%的产率得到ethyl 3-(p-bromo-benzoyl)-5-(2'-pyridyl)-indolizine-1-carboxylate
  参考文献：
  名称：

  Synthesis of indolizine derivatives by the reaction of 2-(2′-pyridyl)-pyridinium ylides with ethylenic dipolarophiles

  摘要：

  The reaction of 2-(2'-pyridyl)-pyridinium N-ylides with substituted ethylenes such as acrylonitrile and ethyl acrylate gave the corresponding tetrahydroindolizine derivatives in high yields. Tetrahydroindolizine derivatives were dehydrogenated by treating with tetrapyridinecobalt(II) bichromate [CoPy4(HCrO4)(2)] to give aromatic indolizines bearing cyano, aroyl, 2'-pyridyl, ester group at the different positions. Seventeen new indolizine derivatives were prepared. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00798-x

文献信息

• Cytotoxic substituted indolizines as new colchicine site tubulin polymerisation inhibitors
  作者：Monica-Cornelia Sardaru、Anda Mihaela Craciun、Cristina-Maria Al Matarneh、Isabela Andreea Sandu、Roxana Maria Amarandi、Lacramioara Popovici、Catalina Ionica Ciobanu、Dragos Peptanariu、Mariana Pinteala、Ionel I. Mangalagiu、Ramona Danac

  DOI：10.1080/14756366.2020.1801671

  日期：2020.1.1

  their anticancer activity against a panel of 60 human cancer cell lines. Compounds 11a, 11b, 15a, and 15j showed a broad spectrum of growth inhibitory activity against cancer cell lines representing leukaemia, melanoma and cancer of lung, colon, central nervous system, ovary, kidney, breast, and prostate. Among them, compound 11a was distinguishable by its excellent cytostatic activity, showing GI50 values

  摘要 合成了潜在的微管失稳系列新吲哚嗪衍生物，并测试了它们对一组60种人类癌细胞系的抗癌活性。化合物11a，11b，15a和15j对代表白血病，黑色素瘤和肺癌，结肠癌，中枢神经系统，卵巢，肾脏，乳腺癌和前列腺癌的癌细胞系显示出广泛的生长抑制活性。其中，化合物11a具有出色的细胞抑制活性，在43种细胞系中显示的GI 50值在10-100 nM范围内。根据GI 50，效力较低的化合物15a和15j值显示出对测试的结肠癌，中枢神经系统癌，肾癌和黑色素瘤细胞系具有高细胞毒性作用，并且仅对其他类型癌症中的少数细胞系有作用。体外测定显示所有活性化合物均抑制微管蛋白聚合。分子对接显示活性化合物与微管蛋白的秋水仙碱结合位点具有良好的互补性。
• Synthesis of 5-(2′-pyridyl)-indolizines by the reaction of 2-(2′-pyridyl)-pyridinium-ylides with activated alkynes
  作者：Ioan I. Druta、Mioara A. Andrei、Pompiliu S. Aburel

  DOI：10.1016/s0040-4020(97)10419-7

  日期：1998.3

  New heterocyclic compounds, indolizine derivatives, were prepared by 3+2 dipolar cycloaddition reactions. These compounds were synthesized by the reaction of 2-(2′-pyridyl)-pyridinium-ylides 5–8 with dimethyl acetylenedicarboxylate or ethyl propiolate. The structure of the new compounds was established by elemental analysis (C,H,N) and IR and 1HNMR spectral methods.

  通过3 + 2偶极环加成反应制备了新的杂环化合物吲哚嗪衍生物。这些化合物是由2-（2'-吡啶基）-吡啶基吡啶5-8与乙炔二羧酸二甲酯或丙酸乙酯反应而合成的。通过元素分析（C，H，N），IR和1 HNMR光谱方法确定了新化合物的结构。