1-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenylcyclohexane-1-carboxylic acid | 365550-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenylcyclohexane-1-carboxylic acid
• 英文别名: Fmoc-Apc-OH
• CAS: 365550-63-6
• 化学式: C₂₈H₂₇NO₄
• 分子量: 441.527
• InChiKey: VRDHFYXVHXGOJV-JWZXCJSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenylcyclohexane-1-carboxylic acid 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.5h， 生成
  参考文献：
  名称：

  Discovery of 1-amino-4-phenylcyclohexane-1-carboxylic acid and its influence on agonist selectivity between human melanocortin-4 and -1 receptors in linear pentapeptides

  摘要：

  Linear pentapeptides (Penta-cis-Apc-DPhe-Arg-Trp-Gly-NH2) containing 1-amino-4-phenylcyclohexane-1-carboxylic acid (cis-Apc) and substituted Apc are potent hMC4R agonists and they are inactive or weakly active in hMC1R, hMC3R, and hMC5R agonist assays. This study, together with our earlier report on 5-BrAtc, demonstrated the importance of replacing His6 with phenyl-containing rigid templates in achieving good hMC4R agonist potency and selectivity against hMC1R in linear pentapeptides.

  DOI：

  10.1016/j.bmcl.2005.08.012
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 1-氨基-4-苯基环己烷羧酸 以 1,4-二氧六环 、 水 为溶剂， 生成 、 1-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenylcyclohexane-1-carboxylic acid
  参考文献：
  名称：

  Discovery of 1-amino-4-phenylcyclohexane-1-carboxylic acid and its influence on agonist selectivity between human melanocortin-4 and -1 receptors in linear pentapeptides

  摘要：

  Linear pentapeptides (Penta-cis-Apc-DPhe-Arg-Trp-Gly-NH2) containing 1-amino-4-phenylcyclohexane-1-carboxylic acid (cis-Apc) and substituted Apc are potent hMC4R agonists and they are inactive or weakly active in hMC1R, hMC3R, and hMC5R agonist assays. This study, together with our earlier report on 5-BrAtc, demonstrated the importance of replacing His6 with phenyl-containing rigid templates in achieving good hMC4R agonist potency and selectivity against hMC1R in linear pentapeptides.

  DOI：

  10.1016/j.bmcl.2005.08.012

文献信息

• Design, synthesis and biological activity of new neurohypophyseal hormones analogues conformationally restricted in the N-terminal part of the molecule. Highly potent OT receptor antagonists
  作者：Anna Kwiatkowska、Monika Ptach、Lenka Borovičková、Jiřina Slaninová、Bernard Lammek、Adam Prahl

  DOI：10.1007/s00726-011-1109-6

  日期：2012.8

  In this study we present the synthesis and some pharmacological properties of fourteen new analogues of neurohypophyseal hormones conformationally restricted in the N-terminal part of the molecule. All new peptides were substituted at position 2 with cis-1-amino-4-phenylcyclohexane-1-carboxylic acid (cis-Apc). Moreover, one of the new analogues: [cis-Apc2, Val4]AVP was also prepared in N-acylated forms

  在这项研究中，我们介绍了 14 种新的神经垂体激素类似物的合成和一些药理学特性，这些类似物在分子的N端部分构象受到限制。所有新肽在 2 位被顺式-1-氨基-4-苯基环己烷-1-羧酸（顺式-Apc）取代。此外，一种新的类似物：[ cis -Apc 2 , Val 4 ]AVP 也制备成具有各种庞大酰基的N-酰化形式。测试了所有肽的升压、抗利尿和体外子宫收缩活性。我们还确定了所选化合物对人 OT 受体的结合亲和力。我们的结果表明，引入顺式 -装甲运兵2中任一或AVP OT的位置2上导致具有高效力antioxytocin类似物。两种新化合物 [Mpa 1 , cis -Apc 2 ]AVP 和 [Mpa 1 , cis -Apc 2 ,Val 4 ]AVP 是非常有效的抗子宫收缩剂（分别为 pA 2  = 8.46 和 8.40）并表现出更高的亲和力对于人类 OT 受体，比阿托西班 ( K i值
• 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。
• Preparation of human Melanocortin-4 receptor agonist libraries: Linear peptides X-Y-DPhe7-Arg8-Trp(or 2-Nal)9-Z-NH2
  作者：Adrian Wai-Hing Cheung、Lida Qi、Vijay Gore、Xin-Jie Chu、David Bartkovitz、Grazyna Kurylko、Joseph Swistok、Waleed Danho、Li Chen、Keith Yagaloff

  DOI：10.1016/j.bmcl.2005.08.083

  日期：2005.12

  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.