ethyl (S)-N-α-(fluorenylmethyloxycarbonyl)-leucinate

• 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
• 英文名称: ethyl (S)-N-α-(fluorenylmethyloxycarbonyl)-leucinate
• 英文别名: ethyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoate
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: FUZNBWCOAOJKDQ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (S)-N-α-(fluorenylmethyloxycarbonyl)-leucinate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以32%的产率得到N-(fluorenylmethyloxycarbonyl)-L-leucinal
  参考文献：
  名称：

  A Solid-Phase Approach to Mouse Melanocortin Receptor Agonists Derived from a Novel Thioether Cyclized Peptidomimetic Scaffold

  摘要：

  The solid-phase synthesis of a novel thioether cyclized peptidomimetic scaffold, displaying functionality at the i to i+3 positions, is reported. The thioether bridge is formed on-bead by an intramolecular reaction between a chloroacetylated reduced peptide bond and the free thiol from a cysteine. The crude products were obtained in moderate to very high purity. A series of 19 compounds were prepared and tested for agonist activity at the mouse melanocortin receptors 1, 3, 4, and 5 (mMC1-5R). From these results, several compounds were identified as having low micromolar agonist activity at the mMC1R and mMC4R. The former is involved in skin pigmentation and animal coat coloration. The latter is involved in the regulation of appetite and food intake and is currently a drug target for potential treatment of obesity. The most potent compound 1n with the pharmacophore motif "His-DPhe-Arg-Trp" was identified as having an EC50 value of 165 nM at mMC1R, 7600 nM at mMC3R, 650 nM at mMC4R, and 335 nM at mMC5R. In addition, some of the compounds showed moderate selectivity for the mMC1R.

  DOI：

  10.1021/ja0123913
• 作为产物：
  描述：

  L-亮氨酸乙酯 、 氯甲酸-9-芴基甲酯 以 neat (no solvent) 为溶剂， 反应 0.03h， 以88%的产率得到ethyl (S)-N-α-(fluorenylmethyloxycarbonyl)-leucinate
  参考文献：
  名称：

  Greener, Efficient and Catalyst-Free Ultrasonic-Assisted Protocol for theN-Fmoc Protection of Amines

  摘要：

  A simple, eco-sustainable method for the N-(9-fluorenylmethoxycarbonyl) (N-Fmoc) protection of various structurally amines under ultrasonic irradiation is reported. The corresponding N- Fmoc derivatives were obtained in good to excellent yields within short reaction time. The reaction proceeds without the formation of any side product. Mildness, efficiency and easier work are the main advantages of this new protocol.

  DOI：

  10.5935/0103-5053.20150286

文献信息

• Sureshbabu, Vommina V.; Vasantha; Madhu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 7, p. 895 - 900
  作者：Sureshbabu, Vommina V.、Vasantha、Madhu

  DOI：——

  日期：——
• [EN] PHOTOCHEMICAL PROCESS FOR THE FLUORINATION OF AN ORGANIC COMPOUND HAVING AN UNACTIVATED SP3 C-H BOND<br/>[FR] PROCÉDÉ PHOTOCHIMIQUE DE FLUORATION D'UN COMPOSÉ ORGANIQUE PRÉSENTANT UNE LIAISON C-H SP3 NON ACTIVÉE
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2015000076A9

  公开（公告）日：2015-08-06
• EP0531443A4
  申请人：——

  公开号：EP0531443A4

  公开（公告）日：1993-04-21
• METHODS FOR TREATING INFLAMMATION AND COMPOUNDS AND COMPOSITIONS SUITABLE FOR USE THEREIN
  申请人：WEITZBERG, Moshe

  公开号：EP0531443A1

  公开（公告）日：1993-03-17
• [EN] METHODS FOR TREATING INFLAMMATION AND COMPOUNDS AND COMPOSITIONS SUITABLE FOR USE THEREIN
  申请人：WEITZBERG, Moshe

  公开号：WO1991018596A1

  公开（公告）日：1991-12-12

  (EN) The present invention relates to a method of treating an inflammatory condition, and to compounds and composition suitable for use in such a method, which compounds have formula (I) wherein: X is methylene, ethylene, ethyleneoxy, or oxygen; Q is (a) where C' is a residue of a lipophilic amino acid, and Y is -CO2H, -CH2OH, -CONR1R2, or -CO2R1 where R1 and R2 are hydrogen, alkyl, or aryl; R3 and R4 are, independently, hydrogen, alkyl or aryl; and A and B are, independently, hydrogen, fused phenyl, alkyl, aryl, alkaryl, aralkyl, alkoxy, alkoxyalkyl, halogen, or nitro; or pharmaceutically acceptable salts thereof.(FR) Procédé de traitement d'états inflammatoires, composés et composition adaptés pour être utilisés dans ledit procédé. Lesdits composés ont la formule (I), dans laquelle X représente méthylène, éthylène, éthylèneoxy ou oxygène; Q représente la formule (II) dans laquelle C' représente un reste d'un acide aminé lipophile, et Y représente -CO2H, -CO2OH, -CONR1R2, ou -CO2R1, où R1 et R2 représentent hydrogène, alkyle ou aryle; R3 et R4 représentent indépendamment hydrogène, alkyle ou aryle; et A ainsi que B représentent, indépendamment, hydrogène, phényle fusionné, alkyle, aryle, alcaryle, aralkyle, alcoxy, alcoxyalkyle, halogène ou nitro; ou ses sels pharmaceutiquement acceptables.