N-Boc-DL-α-methyl tryptophan | 114779-79-2

• 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: N-Boc-DL-α-methyl tryptophan
• 英文别名: 2-[(t-Butyloxy)-carbonyl]-amino-3-(1H-indol-3-yl)-2RS-methyl-propionic acid；N-tert-Butyloxycarbonyl-α-methyltryptophan；Boc-alpha-methyl-DL-tryptophan；3-(1H-indol-3-yl)-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 114779-79-2
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: LJPMZDOWNYFYCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-Boc-DL-α-methyl tryptophan 在 ammonium acetate 、 caesium carbonate 作用下， 以 对二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 生成 Tert-butyl (1-(1H-indol-3-yl)-2-(5-phenyl-1H-imidazol-2-yl)propan-2-yl)carbamate
  参考文献：
  名称：

  SAR exploration at the C-3 position of tetrahydro-β-carboline sstr3 antagonists

  摘要：

  MK-4256, a tetrahydro-beta-carboline sstr3 antagonist, was discontinued due to a cardiovascular (CV) adverse effect observed in dogs. Additional investigations revealed that the CV liability (QTc prolongation) was caused by the hERG off-target activity of MK-4256 and was not due to sstr3 antagonism. In this Letter, we describe our extensive SAR effort at the C3 position of the tetrahydro-beta-carboline structure. This effort resulted in identification of 5-fluoro-pyridin-2-yl as the optimal substituent on the imidazole ring to balance sstr3 activity and the hERG off-target liability. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.02.022
• 作为产物：
  描述：

  Alpha-甲基-DL-色氨酸 、 二碳酸二叔丁酯 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以58%的产率得到N-Boc-DL-α-methyl tryptophan
  参考文献：
  名称：

  α-Methyl tryptophanylphenylalanines and their arylethylamine “dipeptoid” analogues of the tetrapeptide cholecystokinin (30–33)

  摘要：

  DOI：

  10.1016/0223-5234(90)90164-x

文献信息

• BETA CARBOLINE DERIVATIVES AS ANTIDIABETIC COMPOUNDS
  申请人：Dobbelaar Peter H.

  公开号：US20100184758A1

  公开（公告）日：2010-07-22

  Beta-carboline derivatives of structural formula I are selective antagonists of the somatostatin subtype receptor 3 (SSTR3) and are useful for the treatment of Type 2 diabetes mellitus and of conditions that are often associated with this disease, including hyperglycemia, insulin resistance, obesity, lipid disorders, and hypertension. The compounds are also useful for the treatment of depression and anxiety.

  结构式I的β-咔啉衍生物是生长抑素亚型受体3（SSTR3）的选择性拮抗剂，可用于治疗2型糖尿病以及通常与该疾病相关的病症，包括高血糖、胰岛素抵抗、肥胖、脂质异常和高血压。这些化合物还可用于治疗抑郁症和焦虑症。
• 2-Substituted-[2-substituted-amino]-N-aralkyl-3-[indol-3-yl]propanamides
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0224151A2

  公开（公告）日：1987-06-03

  Certain 2-substituted-[2-substituted-aminol-N-arylalkyl-3-[indo]-3-yl]propanamides demonstrate activity as appetite suppressants. The compounds, pharmaceutical compositions, and a method of suppressing appetite are disclosed.

  某些 2-取代-[2-取代-氨基醇-N-芳基烷基-3-[吲哚]-3-基]丙酰胺具有抑制食欲的活性。 本文公开了这些化合物、药物组合物和一种抑制食欲的方法。
• Novel Compounds for Regeneration of Terminally-Differentiated Cells and tissues
  申请人：Acousia Therapeutics GmbH

  公开号：EP2871181B1

  公开（公告）日：2016-10-05
• HORWELL, DAVID C.;BIRCHMORE, BARBARA;BODEN, PHILLIP R.;HIGGINBOTTOM, MICH+, EUR. J. MED. CHEM., 25,(1990) N, C. 53-60
  作者：HORWELL, DAVID C.、BIRCHMORE, BARBARA、BODEN, PHILLIP R.、HIGGINBOTTOM, MICH+

  DOI：——

  日期：——
• HORWELL, DAVID C.
  作者：HORWELL, DAVID C.

  DOI：——

  日期：——