ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate | 64258-95-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate
• 英文别名: formylamino-indol-3-ylmethyl-malonic acid diethyl ester；Formylamino-indol-3-ylmethyl-malonsaeure-diaethylester；2-Formamido-3-(3-indolyl)-2-carbethoxypropionic acid ethyl ester；N-Formyl-α-carbethoxytryptophanethylester；Diethyl formamido[(1H-indol-3-yl)methyl]propanedioate；diethyl 2-formamido-2-(1H-indol-3-ylmethyl)propanedioate
• CAS: 64258-95-3
• 化学式: C₁₇H₂₀N₂O₅
• 分子量: 332.356
• InChiKey: ZAIGSUKBOXJYBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate 在 sodium hydroxide 、 水 作用下， 生成 DL-色氨酸
  参考文献：
  名称：

  Vejdelek, Chemicke Listy, 1950, vol. 44, p. 73,74

  摘要：

  DOI：
• 作为产物：
  描述：

  吲哚 在 sodium hydroxide 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate
  参考文献：
  名称：

  Structure–activity relationship study of novel necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-alpha. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.077

文献信息

• Model studies related to the total synthesis of the fumitremorgins; the Pictet-Spengler cyclisation and the formation and intramolecular acylation of a 1,2-dihydro-β-carboline derivative
  作者：David M. Harrison、Ram Bilas Sharma

  DOI：10.1016/s0040-4020(01)89899-9

  日期：1993.4

  tetrahydro-β-carbolines 8, 9b, and 9d are described. The Pictet-Spengler reaction of L-tryptophyl-L-proline methyl ester with 3-methylbutanal gave the tetrahydro-β-carbolines 20 and 21; subsequent acid-catalysed cyclisation afforded the fumitremorgin analogues 22 and 23. The 2-(p-toluenesulphonyl)tetrahydro-β-carboline 27a furnished the unsaturated pentacycle 28a upon treatment with alkali.

  的四氢β咔啉的制剂8，图9B，和图9d中描述。L-色氨酸-L-脯氨酸甲酯与3-甲基丁醛的Pictet-Spengler反应得到四氢-β-咔啉20和21。随后的酸催化环化提供了fumitremorgin类似物22和23。在用碱处理后，2-（对甲苯磺酰基）四氢-β-咔啉27a提供了不饱和五环28a。
• Inhibitors of cellular necrosis
  申请人：Cuny D. Gregory

  公开号：US20050119260A1

  公开（公告）日：2005-06-02

  The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.

  本发明涉及化合物、药物制剂及其在预防或治疗与细胞死亡相关的创伤、缺血、中风和退行性疾病中的应用的治疗。本发明的方法和组合物特别适用于治疗与细胞坏死相关的神经系统疾病。
• Palladium-catalysed imidoylative spirocyclization of 3-(2-isocyanoethyl)indoles
  作者：Shi Tang、Shumin Ding、Dan Li、Lianjie Li、Haixia Zhao、Minxue Chai、Jian Wang

  DOI：10.1039/d1cc03240b

  日期：——

  and an imidoylative spirocyclization cascade. Additionally, a tandem dearomatization of two different indoles was realized with N-(2-bromobenzoyl)indoles as the electrophilic coupling partner of 3-(2-isocyanoethyl)indoles, affording polyindoline – spiroindoline bisheterocyclic scaffolds conveniently. Under the catalysis of Pd(OAc)2 and a spinol-derived phosphoramidite ligand, chiral spiroindolines were

  钯催化的螺二氢吲哚通过 3-(2-异氰乙基) 吲哚的脱芳环化反应被开发出来。2'-芳基-、乙烯基-和烷基-取代的螺二氢吲哚可以在温和条件下获得，具有优异的官能团耐受性。C1-tethered oxindole-和 indole-spiroindoline bisheterocycles通过烯烃/丙二烯插入和亚氨基化螺环化级联以高产率生成。此外，利用N- (2-溴苯甲酰基)吲哚作为3-(2-异氰乙基)吲哚的亲电偶联伙伴实现了两种不同吲哚的串联脱芳构化，方便地提供了聚二氢吲哚-螺二氢吲哚双杂环支架。在Pd(OAc) 2的催化下 和衍生自旋旋醇的亚磷酰胺配体，手性螺二氢吲哚以高达 95% 的产率和 85% 的 ee 成功获得。
• Novel syntheses of tryptophans
  申请人：Hoffmann-La Roche Inc.

  公开号：US04256641A1

  公开（公告）日：1981-03-17

  The preparation of racemic and optically pure tryptophans is described. The D-enantiomers of the 6-substituted compounds possess a potent sweetening capability. Novel intermediates are also disclosed.

  本文描述了混合型和光学纯的色氨酸的制备方法。6-取代化合物的D-对映体具有强大的甜味能力。此外，本文还披露了新型的中间体。
• Synthesis of tryptophans
  申请人：Hoffmann-La Roche Inc.

  公开号：US04073795A1

  公开（公告）日：1978-02-14

  The preparation of racemic and optically pure tryptophans is described. The D-enantiomers of the 6-substituted compounds possess a potent sweetening capability. Novel intermediates are also disclosed.

  描述了制备外消旋和光学纯色色氨酸的方法。6-取代化合物的D-对映体具有强烈的甜味能力。还公开了新的中间体。