2-methyltryptophan methyl ester | 743373-13-9

• 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-methyltryptophan methyl ester
• 英文别名: methyl (2S)-2-amino-3-(2-methyl-1H-indol-3-yl)propanoate
• CAS: 743373-13-9
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: AAGMGVFODZUQBI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基肉桂酸 、 2-methyltryptophan methyl ester 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (S, E)-methyl 3-(2-methyl-1H-indol-3-yl)-2-(3-(3,4,5-trimethoxyphenyl)acrylamido)propanoate
  参考文献：
  名称：

  Lead Optimization Studies of Cinnamic Amide EP2 Antagonists

  摘要：

  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.

  DOI：

  10.1021/jm5000672

文献信息

• Lavendamycin analogues and methods of synthesizing and using lavendamycin analogues
  申请人：Behforouz Mohammad

  公开号：US20060079497A1

  公开（公告）日：2006-04-13

  Lavendamycin analogues, methods for their synthesis, and methods for their use in the treatment of diseases such as cancer and HIV infection are described.

  Lavendamycin类似物，其合成方法，以及在治疗癌症和HIV感染等疾病中使用的方法被描述。
• Exploring the Biosynthetic Potential of TsrM, a B ₁₂ ‐dependent Radical SAM Methyltransferase Catalyzing Non‐radical Reactions
  作者：Feryel Soualmia、Alain Guillot、Nazarii Sabat、Clémence Brewee、Xavier Kubiak、Michael Haumann、Xavier Guinchard、Alhosna Benjdia、Olivier Berteau

  DOI：10.1002/chem.202200627

  日期：2022.6

  catalyzing methylation reactions from carbon-atoms to nucleophilic atoms making it a unique and versatile alkylating agent. TsrM is able to directly transfer methyl groups on the less reactive carbon atom of the indole ring and to install several methyl groups on its substrate. TsrM has thus unique properties among radical SAM enzymes by notably catalyzing non-radical reactions. (SAM: S-adenosyl-L-methionine)

  TsrM 是一种 B 12依赖性自由基 SAM 酶，可催化从碳原子到亲核原子的甲基化反应，使其成为一种独特且用途广泛的烷化剂。TsrM 能够直接转移吲哚环反应性较低的碳原子上的甲基，并在其底物上安装几个甲基。因此，通过显着催化非自由基反应，TsrM 在自由基 SAM 酶中具有独特的特性。（SAM：S-腺苷-L-蛋氨酸）。
• LAVENDAMYCIN ANALOGS, THEIR USE AND PREPARATION
  申请人：BEHFOROUZ, Mohammad

  公开号：EP0701557A1

  公开（公告）日：1996-03-20
• EP0701557A4
  申请人：——

  公开号：EP0701557A4

  公开（公告）日：1997-07-09
• US5525611A
  申请人：——

  公开号：US5525611A

  公开（公告）日：1996-06-11