2-(3-chlorobenzoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-chlorobenzoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester
• 英文别名: (S)-methyl N-(3-chlorobenzoyl)tryptophanoate；methyl (2S)-2-[(3-chlorobenzoyl)amino]-3-(1H-indol-3-yl)propanoate
• 化学式: C₁₉H₁₇ClN₂O₃
• 分子量: 356.809
• InChiKey: HYDPJHYSXAMTGU-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-chlorobenzoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 在 sodium hydroxide 作用下， 以72%的产率得到CR 546
  参考文献：
  名称：

  Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors

  摘要：

  Glycosidases, including beta-d-galactosidase and beta-d-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several beta-d-galactosidase and beta-d-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as beta-d-galactosidase and beta-d-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 A mu M) and 4d (49 % inhibition at 100 A mu M) exhibited the best inhibitory bioactivities against beta-d-galactosidase and beta-d-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.

  DOI：

  10.1007/s00044-014-1314-4
• 作为产物：
  描述：

  3-氯苯甲酰氯 、 L-色氨酸甲酯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以86%的产率得到2-(3-chlorobenzoylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  A Photoactivated Precipiton for Reagent Sequestration in Solution-Phase Synthesis

  摘要：

  Precipitons are molecular phase tags for chemical separations. They can be switched from a high-solubility to a low-solubility state to facilitate product, reagent, or catalyst isolation. This paper presents the first photoactivated precipiton and demonstrates that this precipiton is an efficient amine scavenging agent in solution-phase syntheses of amides, ureas, and imines. This approach to amine scavenging offers advantages over solid-phase scavenging methods. The amine is captured in a homogeneous medium, so the capture is much faster than seen with isocyanate resins, and only a small excess of the scavenger is required.

  DOI：

  10.1021/ja017577g

文献信息

• A Photoactivated Precipiton for Reagent Sequestration in Solution-Phase Synthesis
  作者：Todd Bosanac、Craig S. Wilcox

  DOI：10.1021/ja017577g

  日期：2002.4.1

  Precipitons are molecular phase tags for chemical separations. They can be switched from a high-solubility to a low-solubility state to facilitate product, reagent, or catalyst isolation. This paper presents the first photoactivated precipiton and demonstrates that this precipiton is an efficient amine scavenging agent in solution-phase syntheses of amides, ureas, and imines. This approach to amine scavenging offers advantages over solid-phase scavenging methods. The amine is captured in a homogeneous medium, so the capture is much faster than seen with isocyanate resins, and only a small excess of the scavenger is required.
• Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors
  作者：Reema Abu Khalaf、Ahmed Mutanabbi Abdula、Mohammad S. Mubarak、Mutasem O. Taha

  DOI：10.1007/s00044-014-1314-4

  日期：2015.6

  Glycosidases, including beta-d-galactosidase and beta-d-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several beta-d-galactosidase and beta-d-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as beta-d-galactosidase and beta-d-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 A mu M) and 4d (49 % inhibition at 100 A mu M) exhibited the best inhibitory bioactivities against beta-d-galactosidase and beta-d-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.