(R)-1-[3-(tert-butoxycarbonylamino)propyl]carbamoyl-2-(1H-indol-3-yl)ethylcarbamic acid tert-butyl ester | 577978-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-1-[3-(tert-butoxycarbonylamino)propyl]carbamoyl-2-(1H-indol-3-yl)ethylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-[[(2R)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propyl]carbamate
• CAS: 577978-05-3
• 化学式: C₂₄H₃₆N₄O₅
• 分子量: 460.574
• InChiKey: VOWALDMXRUYSRN-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-[3-(tert-butoxycarbonylamino)propyl]carbamoyl-2-(1H-indol-3-yl)ethylcarbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以48%的产率得到
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of non-peptidic ligands at the Xenopus laevis skin-melanocortin receptor

  摘要：

  Taking the tripeptide D-Trp-Arg-Leu-NH2 as a lead for a Xenopus laevis skin-melanocortin (MC) receptor antagonist, thirteen non-peptidic compounds were synthesized and biologically evaluated at Xenopus laevis melanophores. Six competitive antagonists (shown by Schild analysis) and one partial agonist were identified with moderate activity (IC50: 5-10 muM). Tryptophanamides with aliphatic side chains were inactive whereas basic residues restored activity. Introducing an imidazole residue yielded partial agonist activity (EC50: 32 muM). Interestingly, constraining the inactive S-tryptophan-isoamylamide to a beta-carboline ring yielded an MC receptor antagonist (42). The specificity for MC receptors was tested at various G-protein coupled receptors. In conclusion, the synthesis of non-peptidic MC receptor antagonists is described which may serve as lead compounds for further studies. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00062-x
• 作为产物：
  描述：

  D-色氨酸 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 (R)-1-[3-(tert-butoxycarbonylamino)propyl]carbamoyl-2-(1H-indol-3-yl)ethylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of non-peptidic ligands at the Xenopus laevis skin-melanocortin receptor

  摘要：

  Taking the tripeptide D-Trp-Arg-Leu-NH2 as a lead for a Xenopus laevis skin-melanocortin (MC) receptor antagonist, thirteen non-peptidic compounds were synthesized and biologically evaluated at Xenopus laevis melanophores. Six competitive antagonists (shown by Schild analysis) and one partial agonist were identified with moderate activity (IC50: 5-10 muM). Tryptophanamides with aliphatic side chains were inactive whereas basic residues restored activity. Introducing an imidazole residue yielded partial agonist activity (EC50: 32 muM). Interestingly, constraining the inactive S-tryptophan-isoamylamide to a beta-carboline ring yielded an MC receptor antagonist (42). The specificity for MC receptors was tested at various G-protein coupled receptors. In conclusion, the synthesis of non-peptidic MC receptor antagonists is described which may serve as lead compounds for further studies. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00062-x

文献信息

• Design, synthesis, and biological evaluation of non-peptidic ligands at the Xenopus laevis skin-melanocortin receptor
  作者：Ursula Tammler、J Mark Quillan、Jochen Lehmann、Wolfgang Sadée、Matthias U Kassack

  DOI：10.1016/s0223-5234(03)00062-x

  日期：2003.5

  Taking the tripeptide D-Trp-Arg-Leu-NH2 as a lead for a Xenopus laevis skin-melanocortin (MC) receptor antagonist, thirteen non-peptidic compounds were synthesized and biologically evaluated at Xenopus laevis melanophores. Six competitive antagonists (shown by Schild analysis) and one partial agonist were identified with moderate activity (IC50: 5-10 muM). Tryptophanamides with aliphatic side chains were inactive whereas basic residues restored activity. Introducing an imidazole residue yielded partial agonist activity (EC50: 32 muM). Interestingly, constraining the inactive S-tryptophan-isoamylamide to a beta-carboline ring yielded an MC receptor antagonist (42). The specificity for MC receptors was tested at various G-protein coupled receptors. In conclusion, the synthesis of non-peptidic MC receptor antagonists is described which may serve as lead compounds for further studies. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.