N-(furan-2-ylmethyl)tryptophan methyl ester

• 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-(furan-2-ylmethyl)tryptophan methyl ester
• 英文别名: methyl (2S)-2-(furan-2-ylmethylamino)-3-(1H-indol-3-yl)propanoate
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: QHQJLDHRZXQOPQ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  67.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(furan-2-ylmethyl)tryptophan methyl ester 在 palladium diacetate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 56.0h， 生成 methyl (10S,12R)-11-(furan-2-ylmethyl)-19-methylidene-1,11-diazapentacyclo[10.8.1.02,7.08,21.013,18]henicosa-2,4,6,8(21),13,15,17-heptaene-10-carboxylate
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1
• 作为产物：
  描述：

  2-(furan-2-ylmethyleneamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以98%的产率得到N-(furan-2-ylmethyl)tryptophan methyl ester
  参考文献：
  名称：

  Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes

  摘要：

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00628-1

文献信息

• Design, synthesis, and characterization of piperazinedione-based dual protein inhibitors for both farnesyltransferase and geranylgeranyltransferase-I
  作者：Yuqin Qiao、Jinbo Gao、Yongge Qiu、Long Wu、Fei Guo、Kenneth Kam-Wing Lo、Ding Li

  DOI：10.1016/j.ejmech.2011.03.007

  日期：2011.6

  Farnesyltransferase (FTase) and geranylgeranyltransferase type-I (GGTase-I) both catalyze the prenylation of protein substrate containing a typical -CAAX motif at the carboxyl terminus. The inhibitors for these two enzymes have been widely studied as potential cancer chemotherapeutic agents. In the present study, various piperazinedione derivatives were designed and synthesized as a new type of peptide mimetic compounds, which were characterized and found to be dual protein inhibitors for both FTase and GGTase-l. These compounds have similar chemical and physical properties to -CAAX motif of the protein substrate, which may facilitate their transfer to appropriate drug target in vivo. The best inhibitor compound 26b was found to occupy both isoprenoid and peptide substrate binding sites through kinetics and computer molecular docking studies. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Pictet–Spengler/Palladium Catalyzed Allenylation and Carbonylation Processes
  作者：Ronald Grigg、William S MacLachlan、David T MacPherson、Visuvanathar Sridharan、Selvaratnam Suganthan、Mark Thornton-Pett、Jin Zhang

  DOI：10.1016/s0040-4020(00)00628-1

  日期：2000.8

  The tactical combination of the Pictet-Spengler reaction with Pd catalyzed reactions with allene and with carbon monoxide provides rapid access to a range of tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives via intramolecular trapping of intermediate pi-allyl- and acyl-palladium(II) complexes by the indolic or secondary amino moieties generating fused azepine and delta-lactam derivatives. Chiral tryptophan examples are also described. (C) 2000 Elsevier Science Ltd. All rights reserved.