(S)-3-(3-methylbytylcarbamoyl)-1,3,4,9-tetrahydro-2H-β-carboline-2-carboxylic acid tert-butyl ester | 577978-16-6

• 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: (S)-3-(3-methylbytylcarbamoyl)-1,3,4,9-tetrahydro-2H-β-carboline-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3S)-3-(3-methylbutylcarbamoyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
• CAS: 577978-16-6
• 化学式: C₂₂H₃₁N₃O₃
• 分子量: 385.506
• InChiKey: JCBHSQLFZICSHY-IBGZPJMESA-N

物化性质

• 沸点：
  586.9±50.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  74.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-(3-methylbytylcarbamoyl)-1,3,4,9-tetrahydro-2H-β-carboline-2-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.33h， 以77%的产率得到(S)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid 3-methylbutylamide hydrochloride
  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：

  (S)-2,3,4,9-四氢-1H-吡啶[3,4-b]吲哚-3-羧酸 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 (S)-3-(3-methylbytylcarbamoyl)-1,3,4,9-tetrahydro-2H-β-carboline-2-carboxylic 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.