N-((3S)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-proline | 900866-10-6

• 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: N-((3S)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-proline
• 英文别名: N-[(3S)-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-L-proline
• CAS: 900866-10-6
• 化学式: C₁₇H₁₉N₃O₃
• 分子量: 313.356
• InChiKey: JQAJOQHNJNZJLW-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85.43
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((3S)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-proline 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以87%的产率得到(5aS,14aS)-5,1-dioxo-1,2,3,5,5a,6,11,12,14,14a-decahydro-5H,14H-pyrrolo[1",2":4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole
  参考文献：
  名称：

  Toward breast cancer resistance protein (BCRP) inhibitors: design, synthesis of a series of new simplified fumitremorgin C analogues

  摘要：

  In this study, we report the design and synthesis of a series of new simplified fumitremorgin C analogues. The preliminary biological study indicated some of these simplified fumitremorgin C might be developed into breast cancer resistance inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.045
• 作为产物：
  描述：

  BOC-L-1,2,3,4-四氢-Β-咔啉-3-羧酸 在 N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 2.17h， 生成 N-((3S)-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-proline
  参考文献：
  名称：

  Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity

  摘要：

  3-(S)-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid isolated from A. Chinese G. Don was found to possess moderate anti-aggregation activity, but with poor bioavailability. To improve its pharmacological property, we designed and synthesized a series of novel dipeptide analogues by incorporating tetrahydro-beta-carboline-3-carboxylic acid skeleton as an amino acid surrogate (*Trp). It turned out these dipeptide analogues exhibited good membrane permeability based on in vitro Caco-2 cell monolayers permeability assay. As a result, the overall biological properties of these molecules were significantly improved depending on the nature of the amino acid residues introduced onto the 3-position of the tetrahydro-beta-carboline moiety. It was very interesting to notice that these dipeptide analogues (5b,c,h,i,n,o,p,q) displayed a remarkable dual antiaggregatory activity in both of ADP- and PAF-induced platelet aggregation assay, and their aggregation response was significantly higher than that of aspirin (p < 0.01). In addition, these dipeptide analogues were observed for the dose-dependent antithrombotic effect using in vivo rat arterial thrombosis model. The potency of antithrombotic activity of 5h,i,n,p was significantly higher than that of aspirin (n = 12, p < 0.01) at equal dose (5 mu mol/kg). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.026