Fmoc-(rac-5-BrAtc)-OH | 365550-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-(rac-5-BrAtc)-OH
• 英文别名: 5-bromo-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,4-dihydro-1H-naphthalene-2-carboxylic acid
• CAS: 365550-79-4
• 化学式: C₂₆H₂₂BrNO₄
• 分子量: 492.369
• InChiKey: JFGQLWAAKOIWIF-UHFFFAOYSA-N

物化性质

• 沸点：
  694.5±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Fmoc-L-色氨酸 、 NΑ-FMOC-NΩ-(2,2,5,7,8-五甲基苯并二氢吡喃-6-磺酰基)-L-精氨酸 、 Fmoc-2-氨基苯甲酸 、 Fmoc-(rac-5-BrAtc)-OH 、 alkaline earth salt of/the/ methylsulfuric acid 生成 X1-5-BrAtc-DPhe-Arg-Trp-Z9-NH2
  参考文献：
  名称：

  Preparation of human Melanocortin-4 receptor agonist libraries: Linear peptides X-Y-DPhe7-Arg8-Trp(or 2-Nal)9-Z-NH2

  摘要：

  Two libraries of hMC4R agonists, X-Y-DPhe(7)-Arg(8)-2-Nal(9)-Z-NH2 and X-Y-DPhe(7)-Arg(8)-Trp(9)-Z-NH2, totaling 185 peptides were 6 prepared using Irori radiofrequency tagging technology and Argonaut Quest 210 Synthesizer, where X stands for N-caps, Y for His(6) surrogates and Z for Gly(10) surrogates. As a result of this study, His-modified pentapeptides with Trp were found to be more hMC4R potent than the corresponding 2-Nal analogs, novel N-caps and Gly surrogates were identified and 19 new peptides which are potent hMC4R agonists (EC50 1-15 nM) and selective against hMC1R were discovered. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.083
• 作为产物：
  描述：

  8-bromospiro[2,4-dihydro-1H-naphthalene-3,5'-imidazolidine]-2',4'-dione 在 barium dihydroxide 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 Fmoc-(rac-5-BrAtc)-OH
  参考文献：
  名称：

  Structure–Activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH2 at the human melanocortin-1 and -4 receptors: histidine substitution

  摘要：

  Systematic substitution of His(6) residue using non-selective hMC4R pentapeptide agonist (Bu-His(6)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)- NH2) as the template led to the identification of Bu-Atc(6)(2-aminotetraline-2-carboxylic acid)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)-NH2 which showed moderate selectivity towards hMC4R over hMC1R. Further SAR studies resulted in the discovery of Penta-5-BrAtc(6)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)-NH2 and Penta-5-Me(2)NMAtc(6)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)-NH2 which are potent hMC4R agonists and are inactive in hMC1R, hMC3R and hMC5R agonist assays. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00830-2

文献信息

• Selective linear peptides with melanocortin-4 receptor (MC4-R) agonist activity
  申请人：——

  公开号：US20010056179A1

  公开（公告）日：2001-12-27

  Peptides of formulae I, II and III selectively activate melanocortin-4 (MC-4) receptor activity. 1

  公式I、II和III的肽选择性地激活黑色素皮质素-4（MC-4）受体活性。
• Selective cyclic peptides with melanocortin-4 receptor (MC4-R) agonist activity
  申请人：——

  公开号：US20020143141A1

  公开（公告）日：2002-10-03

  Peptides cyclized via disulfide or lactam bridges having melanocortin-4 receptor (MC4-R) agonist activity useful for treatment of obesity.

  经过二硫键或内酰胺桥环化的肽具有黑色素皮质激素受体（MC4-R）激动剂活性，适用于治疗肥胖症。
• Selective linear peptides with melanocor tin-4 receptor (MC4-R) agonist activity
  申请人：——

  公开号：US20030229200A1

  公开（公告）日：2003-12-11

  Peptides of formulae I, II and III that selectively activate melanocortin-4 (MC-4) receptor activity. 1

  化学式为I、II和III的多肽，可选择性激活黑色素细胞激素-4（MC-4）受体活性。
• Selective Linear Peptides with Melanocortin-4 Receptor (MC4-R) Agonist Activity
  申请人：Chen Li

  公开号：US20080177036A1

  公开（公告）日：2008-07-24

  Peptides of formulae I, II and III that selectively activate melanocortin-4 (MC-4) receptor activity.

  化学式为I、II和III的肽，可选择性地激活黑色素细胞激素受体-4（MC-4）的活性。
• SELECTIVE LINEAR PEPTIDES WITH MELANOCORTIN-4 RECEPTOR (MC4-R) AGONIST ACTIVITY
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1272516B1

  公开（公告）日：2008-04-23