2-(1H-indole-2-carboxamido)acetic acid | 68724-93-6

• 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: 2-(1H-indole-2-carboxamido)acetic acid
• 英文别名: N-(indole-2-carbonyl)-glycine；N-(Indol-2-carbonyl)-glycin；2-(1H-indol-2-ylformamido)acetic acid；2-(1H-indole-2-carbonylamino)acetic acid
• CAS: 68724-93-6
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD11131661
• 分子量: 218.212
• InChiKey: BJKDAKXYJCJZBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-indole-2-carboxamido)acetic acid 在 PPA 作用下， 以72%的产率得到1,2,3,4-四氢吡嗪并[1,2-a]吲哚-1,4-二酮
  参考文献：
  名称：

  Suzuki, Hideharu; Shinpo, Kayoko; Yamazaki, Towako, Heterocycles, 1996, vol. 42, # 1, p. 83 - 86

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzyl 2-[[3-(2-chloro-6-nitrophenyl)-2-oxopropanoyl]amino]acetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以94%的产率得到2-(1H-indole-2-carboxamido)acetic acid
  参考文献：
  名称：

  From cyclic dehydrodipeptides to uncommon acyclic peptide mimetics

  摘要：

  1-Acetyl-3 -arylmethylene-2,5-piperazinediones gave N-3-arylpyruvylamino esters by acid-promoted alcoholysis under thermal conditions or microwave irradiation. Compounds obtained from 1-acetyl-3-(o-nitro)arylmethylene-2,5-piperazinediones gave, after reduction of the nitro group and spontaneous cyclization, N-2-indolylcarbonylamino acid derivatives. A similar alcoholysis/reduction sequence applied to dehydrodipeptides bearing a 3(4)-nitroaryl substituent gave N-3(4)-aminophenyi-alpha-ketopropionylamino acid derivatives. Coupling of the free amino group with Boc-protected amino acids gave tripeptide mimetics with a 6-aminoindole-2-carboxylic or a 3(4)-aminophenyl-alpha-ketopropionic acid as the second residue. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.095

文献信息

• Preparation of indole-2-carboxamides by palladium-catalysed carbonylation
  作者：John M. Herbert、Alan H. McNeill

  DOI：10.1016/s0040-4039(98)00215-9

  日期：1998.4

  Palladium-mediated carbonylation of a 2-iodoindole in the presence of an amine provides an efficient method for the preparation of indole-2-carboxamides. The process is clean and rapid, and appears to be general where the amine component is sufficiently non-volatile.

  在胺存在下钯介导的2-碘吲哚的羰基化为制备吲哚-2-羧酰胺提供了一种有效的方法。该方法干净，快速，并且在胺组分足够不挥发的情况下似乎很普遍。
• The design and synthesis of Ala-Glu/iGln mimetics: heterocyclic building blocks for pseudopeptides
  作者：Žiga Jakopin

  DOI：10.1016/j.tetlet.2014.12.035

  日期：2015.1

  Heterocyclic Ala-Glu/i-Gln mimetics, in which one or both carboxylic acid functionalities are bioisosterically replaced by a 1,2,4-oxadiazole ring system, are designed and synthesized. A straightforward route for preparing orthogonally protected 1,2,4-oxadiazole-bearing dipeptide building blocks is presented. These compounds constitute a new series of non-natural dipeptides, capable of being integrated

  设计并合成了杂环Ala-Glu / i-Gln模拟物，其中一个或两个羧酸官能团被1,2,4-恶二唑环系统生物等排取代。提出了制备正交保护的带有1,2,4-恶二唑的二肽结构单元的直接方法。这些化合物构成了一系列新的非天然二肽，能够整合到生物学上相关的肽中。合成从d-谷氨酸开始，并且选择温和的反应条件以允许形成产物。
• <i>N</i>^G-Acylated Imidazolylpropylguanidines as Potent Histamine H₄ Receptor Agonists: Selectivity by Variation of the <i>N</i>^G-Substituent
  作者：Patrick Igel、Erich Schneider、David Schnell、Sigurd Elz、Roland Seifert、Armin Buschauer

  DOI：10.1021/jm9000693

  日期：2009.4.23

  3-(1H-Imidazol-4-yl)propylguanidine (SK&F 91486, 4) was identified as a potent partial agonist at the human histamine H-3 receptor (hH(3)R) and human histamine H-4 receptor (hH(4)R). With the aim to increase selectivity for the hH4R, the guanidine group in 4 was acylated. N-1-Acetyl-N-2-[3-(1H-imidazol-4-yl)propyl]guanidine (UR-PI288, 13) was a potent full agonist at the hH(4)R (pEC(50) = 8.31; alpha = 1.00), possessing more than 1000- and 100-fold selectivity relative to the hH(1)R and hH(2)R, respectively, and possessing only low intrinsic activity (alpha = 0.27) at the hH(3)R.
• Varnavas; Lassiani; Luxich, Il Farmaco, 1996, vol. 51, # 5, p. 341 - 350
  作者：Varnavas、Lassiani、Luxich、Zacchigna、Boccu、Pichierri

  DOI：——

  日期：——
• Gliotoxin. VII. Synthesis of Pyrazinoindolones and Pyridindolones¹
  作者：John R. Johnson、Aubrey A. Larsen、Ann D. Holley、Koert Gerzon

  DOI：10.1021/ja01202a034

  日期：1947.10