3-(2-甲基-吲哚-1-基)-丙酸 | 42951-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-(2-甲基-吲哚-1-基)-丙酸
• 英文名称: 3-(2-methyl-1H-indol-1-yl)propanoic acid
• 英文别名: 3-(2-methyl-indol-1-yl)-propionic acid；3-(2-Methyl-indol-1-yl)-propionsaeure；3-(2-methylindol-1-yl)propanoic acid
• CAS: 42951-33-7
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD06589832
• 分子量: 203.241
• InChiKey: OJDOEXJZNZKRBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(2-甲基-吲哚-1-基)-丙酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 (R)-3-(4-(3-ethyl-3-hydroxypent-1-ynyl)phenyl)-2-(3-(2-methyl-1H-indol-1-yl)propanamido)propanoic acid
  参考文献：
  名称：

  Discovery of Small-Molecule Interleukin-2 Inhibitors from a DNA-Encoded Chemical Library

  摘要：

  AbstractLibraries of chemical compounds individually coupled to encoding DNA tags (DNA‐encoded chemical libraries) hold promise to facilitate exceptionally efficient ligand discovery. We constructed a high‐quality DNA‐encoded chemical library comprising 30 000 drug‐like compounds; this was screened in 170 different affinity capture experiments. High‐throughput sequencing allowed the evaluation of 120 million DNA codes for a systematic analysis of selection strategies and statistically robust identification of binding molecules. Selections performed against the tumor‐associated antigen carbonic anhydrase IX (CA IX) and the pro‐inflammatory cytokine interleukin‐2 (IL‐2) yielded potent inhibitors with exquisite target specificity. The binding mode of the revealed pharmacophore against IL‐2 was confirmed by molecular docking. Our findings suggest that DNA‐encoded chemical libraries allow the facile identification of drug‐like ligands principally to any protein of choice, including molecules capable of disrupting high‐affinity protein–protein interactions.

  DOI：

  10.1002/chem.201200952
• 作为产物：
  描述：

  3-(2-methyl-indol-1-yl)-propionitrile 在 氢氧化钾 作用下， 生成 3-(2-甲基-吲哚-1-基)-丙酸
  参考文献：
  名称：

  Terent'ew et al., Zhurnal Obshchei Khimii, 1955, vol. 25, p. 1959,1962; engl. Ausg. S. 1905, 1907

  摘要：

  DOI：

文献信息

• Solvent-promoted catalyst-free regioselective <i>N</i>-incorporation multicomponent domino reaction: rapid assembly of π-functionalized [60]fullerene-fused dihydrocarbolines
  作者：Tong-Xin Liu、Shuaishuai Yue、Changgeng Wei、Nana Ma、Pengling Zhang、Qingfeng Liu、Guisheng Zhang

  DOI：10.1039/c8cc07580h

  日期：——

  Described here is the first example of solvent-promoted catalyst-free N-incorporation multicomponent domino reaction for the direct construction of novel π-extension [60]fullerene-fused dihydrocarbolines from simple hydrocarbons. This unprecedented transformation is proposed to proceed by a sequential N-incorporation/[4+2] cycloaddition/elimination process, involving multiple types of bond cleavage and formation

  在此描述的是第一个通过溶剂促进的无催化剂的N结合多组分多米诺反应的例子，该反应可从简单的烃类直接构建新的π延伸[60]富勒烯稠合的二烃基。提出这种空前的转化是通过顺序的N-掺入/ [4 + 2]环加成/消除过程进行的，该过程涉及在单一化学操作中的多种类型的键裂解和形成。机理研究发现，溶剂对于成功完成转化至关重要，并且涉及多个溶剂辅助的去质子和质子转移是关键步骤。
• Development of Novel Peptidyl Nitriles Targeting Rhodesain and Falcipain-2 for the Treatment of Sleeping Sickness and Malaria
  作者：Carla Di Chio、Josè Starvaggi、Noemi Totaro、Santo Previti、Benito Natale、Sandro Cosconati、Marta Bogacz、Tanja Schirmeister、Jenny Legac、Philip J. Rosenthal、Maria Zappalà、Roberta Ettari

  DOI：10.3390/ijms25084410

  日期：——

  spectrum of action. In this drug discovery process, rhodesain and falcipain-2, of Trypanosoma brucei rhodesiense and Plasmodium falciparum, are currently considered the most promising targets for the development of novel antitrypanosomal and antiplasmodial agents, respectively. Therefore, in our study we identified a novel lead-like compound, i.e., inhibitor 2b, which we proved to be active against both

  近几十年来，被忽视的热带病和与贫困有关的疾病已成为全世界严重的健康问题。在这些疾病中，非洲人类锥虫病和疟疾由于出现耐药性、毒性问题和作用范围有限而存在治疗问题。在这一药物发现过程中，罗得西亚布氏锥虫和恶性疟原虫的罗德赛因和 falcipain-2 目前分别被认为是开发新型抗锥虫和抗疟原虫药物最有希望的靶标。因此，在我们的研究中，我们鉴定了一种新型先导化合物，即抑制剂 2b，我们证明它对这两个靶标均具有活性，对罗得塞因的 Ki = 5.06 µM，对 falcipain-2 的 IC50 = 40.43 µM。
• Lead Optimization Studies of Cinnamic Amide EP2 Antagonists
  作者：Thota Ganesh、Jianxiong Jiang、Myung-Soon Yang、Ray Dingledine

  DOI：10.1021/jm5000672

  日期：2014.5.22

  Prostanoid receptor EP2 can play a proinflammatory role, exacerbating disease pathology in a variety of central nervous system and peripheral diseases. A highly selective EP2 antagonist could be useful as a drug to mitigate the inflammatory consequences of EP2 activation. We recently identified a cinnamic amide class of EP2 antagonists. The lead compound in this class (5d) displays anti-inflammatory and neuroprotective actions. However, this compound exhibited moderate selectivity to EP2 over the DP1 prostanoid receptor (similar to 10-fold) and low aqueous solubility. We now report compounds that display up to 180-fold selectivity against DP1 and up to 9-fold higher aqueous solubility than our previous lead. The newly developed compounds also display higher selectivity against EP4 and IP receptors and a comparable plasma pharmacokinetics. Thus, these compounds are useful for proof of concept studies in a variety of models where EP2 activation is playing a deleterious role.
• DE641597
  申请人：——

  公开号：——

  公开（公告）日：——
• MCDONALD B. G.; PROCTOR G. R., J. CHEM. SOC. PERKIN TRANS., PART I, <JCPK-BH>, 1975, NO 15, 1446-1450
  作者：MCDONALD B. G.、 PROCTOR G. R.

  DOI：——

  日期：——