| 938185-98-9

• 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
• CAS: 938185-98-9
• 化学式: C₂₇H₂₂N₂O₅
• 分子量: 454.482
• InChiKey: JKXIMLZVBUQTLS-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.99
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 sodium carbonate 、 肼 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 C₃₄H₃₀N₂O₅
  参考文献：
  名称：

  Azepinone-Containing Tetrapeptide Analogues of Melanotropin Lead to Selective hMC4R Agonists and hMC5R Antagonist

  摘要：

  To address the need for highly potent, metabolically stable, and selective agonists, antagonists, and inverse agonists at the melanocortin receptor subtypes, conformationally constrained indolo- and benzazepinone residues were inserted into the α-MSH pharmacophore, His(6)-Phe(7)-Arg(8)-Trp(9)-domain. Replacement of His(6) by an aminoindoloazepinone (Aia) or aminobenzazepinone (Aba) moiety led to hMC4R and hMC5R selective agonist and antagonist ligands, respectively (tetrapeptides 1 to 3 and 4, respectively). In peptides 1 to 3 and depending on the para-substituent of the d-Phe residue in position 2, the activity goes from allosteric partial agonism (1, R = H) to allosteric full agonism (2, R = F) and finally allosteric partial agonism (3, R = Br).

  DOI：

  10.1021/ml500436s
• 作为产物：
  描述：

  (S)-N,N-phthaloyl-o-formylphenylalanine 在 N-甲基吗啉 、 吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium cyanoborohydride 、 magnesium sulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 生成
  参考文献：
  名称：

  Azepinone-Containing Tetrapeptide Analogues of Melanotropin Lead to Selective hMC4R Agonists and hMC5R Antagonist

  摘要：

  To address the need for highly potent, metabolically stable, and selective agonists, antagonists, and inverse agonists at the melanocortin receptor subtypes, conformationally constrained indolo- and benzazepinone residues were inserted into the α-MSH pharmacophore, His(6)-Phe(7)-Arg(8)-Trp(9)-domain. Replacement of His(6) by an aminoindoloazepinone (Aia) or aminobenzazepinone (Aba) moiety led to hMC4R and hMC5R selective agonist and antagonist ligands, respectively (tetrapeptides 1 to 3 and 4, respectively). In peptides 1 to 3 and depending on the para-substituent of the d-Phe residue in position 2, the activity goes from allosteric partial agonism (1, R = H) to allosteric full agonism (2, R = F) and finally allosteric partial agonism (3, R = Br).

  DOI：

  10.1021/ml500436s

文献信息

• Novel selective human melanocortin-3 receptor ligands: Use of the 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one (Aba) scaffold
  作者：Steven Ballet、Alexander V. Mayorov、Minying Cai、Dagmara Tymecka、Kevin B. Chandler、Erin S. Palmer、Karolien Van Rompaey、Aleksandra Misicka、Dirk Tourwé、Victor J. Hruby

  DOI：10.1016/j.bmcl.2007.02.020

  日期：2007.5

  In search of new selective antagonists and/or agonists for the human melanocortin receptor subtypes hMC1R to hMC5R to elucidate the specific biological roles of each GPCR, we modified the structures of the superagonist MT-II (Ac-Nle-c[Asp-HiS-D-Phe-Arg-Trp-Lys]-NH2) and the hMC3R/hMC4R antagonist SHU9119 (Ac-Nle-c[Asp-HiS-D-Nal(2 ')-Arg-Trp-Lys]-NH2) by replacing the HiS-D-Phe and HiS-D-Nal(2 ') fragments in MT-II and SHU9119, respectively, with Aba-Xxx (4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one-Xxx) dipeptidomimetics (Xxx = D-Phe/pCl-D-Phe/D-Nal(2 ')). Employment of the Aba mimetic yielded novel selective high affinity hMC3R and hMC3R/hMC5R antagonists. (C) 2007 Elsevier Ltd. All rights reserved.