7'-bromo-N-carbobenzyloxy-L-tryptophan | 496930-07-5

• 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: 7'-bromo-N-carbobenzyloxy-L-tryptophan
• 英文别名: Z-(7-bromo)Trp-OH；(2S)-3-(7-bromo-1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 496930-07-5
• 化学式: C₁₉H₁₇BrN₂O₄
• 分子量: 417.259
• InChiKey: FZJGHOOJOSALCD-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7'-bromo-N-carbobenzyloxy-L-tryptophan 在 氢溴酸 、 氯甲酸乙酯 、 1-羟基苯并三唑 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.83h， 生成 N-Boc-3-iodo-Tyr(Bn)-Ala-7-bromo-Trp-NHMe
  参考文献：
  名称：

  Linear TMC-95-Based Proteasome Inhibitors

  摘要：

  We have designed and evaluated 45 linear analogues of the natural constrained cyclopeptide TMC-95A. These synthetically less demanding molecules are based on the tripeptide sequence Y-N-W of TMC-95A. Structural variations in the amino acid side chains and termini greatly influenced both the efficiency and selectivity of action on a given type of active site. Inhibition constants were submicromolar (K-i approximate to 300 nM) despite the absence of the entropically favorable constrained conformation that is characteristic of TMC-95A and its cyclic analogues. These linear compounds were readily prepared and reasonably stable in culture medium and could be optimized to inhibit one, two, or all three proteasome catalytic sites. Cytotoxicity assays performed on a series of human tumor cell lines identified the most potent inhibitors in cells.

  DOI：

  10.1021/jm0701324
• 作为产物：
  描述：

  N-acetyl-7'-bromo-DL-tryptophan 在 L-aminoacylase 、 sodium carbonate 、 cobalt(II) chloride 作用下， 以 phosphate buffer 、 乙醚 为溶剂， 反应 30.5h， 生成 7'-bromo-N-carbobenzyloxy-L-tryptophan
  参考文献：
  名称：

  Convenient synthesis of 7′ and 6′-bromo-d-tryptophan and their derivatives by enzymatic optical resolution using d-aminoacylase

  摘要：

  Compounds 7' and 61-bromo-D-tryptophan (1 and 2) which are important derivatives for the synthesis of the chloropeptin and kistamycin A, respectively, were conveniently synthesized by optical resolution from N-acetyl-7' and 6-bromo-DL-tryptophan ((RS)-5 and (RS)-14) using D-aminoacylase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00909-2

文献信息

• Compounds Useful as Modulators of the Proteasome Activity
  申请人：Reboud-Ravaux Michele Claude Yvonne

  公开号：US20090069222A1

  公开（公告）日：2009-03-12

  The present invention relates to the use of compounds of the following general formula (I): wherein n o is 0 or 1, and when n o is 1, X=CH 2 or X=NCH 2 C 6 H 5 ; R 1 is OH, or a OR 10 group, or a group of formula NH—(CH 2 ) n1 —R 11 ; R 2 is H, or an alkyl group, or a group of formula (CH 2 ) n2 —(CO) n3 —NR 13 R 14 ; R 3 is H, or an alkyl group; R 4 is H, or Boc, or Z; R 5 is H, or Boc, or Z; R 6 is a OR 16 group; R 7 and R 8 are H, or a halogen atom, as modulators of the proteasome activity, in the frame of the preparation of a medicament useful for the prevention or treatment of diseases wherein the proteasome is involved, or the preparation of cosmetic compositions, or of phytosanitary compositions

  本发明涉及使用以下通式（I）的化合物：其中nois为0或1，当nois为1时，X=CH2或X=NCH2C6H5; R1为OH，或OR10基团，或公式NH—（CH2）n1—R11的基团; R2为H，或烷基，或公式（CH2）n2—（CO）n3—NR13R14的基团; R3为H，或烷基; R4为H，或Boc，或Z; R5为H，或Boc，或Z; R6为OR16基团; R7和R8为H，或卤原子，作为蛋白酶体活性调节剂，用于制备用于预防或治疗蛋白酶体参与的疾病的药物，或制备化妆品组合物或植物保护组合物。
• WO2006/105811
  申请人：——

  公开号：——

  公开（公告）日：——
• COMPOUNDS USEFUL AS MODULATORS OF THE PROTEASOME ACTIVITY
  申请人：Centre National de la Recherche Scientifique

  公开号：EP1865950B1

  公开（公告）日：2013-08-28
• US7919468B2
  申请人：——

  公开号：US7919468B2

  公开（公告）日：2011-04-05
• [EN] COMPOUNDS USEFUL AS MODULATORS OF THE PROTEASOME ACTIVITY<br/>[FR] COMPOSES CONVENANT COMME MODULATEURS DE L'ACTIVITE DU PROTEASOME
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2006105811A1

  公开（公告）日：2006-10-12

  [EN] The present invention relates to the use of compounds of the following general formula (I): wherein n_o is 0 or 1, and when n_o is 1, X = CH₂ or X = NCH₂C₆H₅; R₁ is OH, or a OR₁₀ group, or a group of formula NH-(CH₂)_n1-R₁₁; R₂ is H, or an alkyl group, or a group of formula (CH₂)_n2-(CO)_n3-NR₁₃R₁₄; R₃ is H, or an alkyl group; R₄ is H, or Boc, or Z; R₅ is H, or Boc, or Z ; R₆ is a OR₁₆ group; R₇ and R₈ are H, or a halogen atom, as modulators of the proteasome activity, in the frame of the preparation of a medicament useful for the prevention or treatment of diseases wherein the proteasome is involved, or the preparation of cosmetic compositions, or of phytosanitary compositions.
  [FR] La présente invention concerne des composés représentés par la formule générale (I): dans laquelle n_o vaut 0 ou 1, et, dans le cas où n_o vaut 1, X = CH₂ ou X = NCH₂C₆H₅; R₁ est OH, ou un groupe OR₁₀, ou un groupe de formule NH-(CH₂)_n1-R₁₁; R₂ est H, ou un groupe alkyle, ou un groupe de formule (CH₂)_n2-(CO)_n3-NR₁₃R₁₄; R₃ est H, ou un groupe alkyle; R₄ est H, ou Boc, ou Z; R₅ est H, ou Boc, ou Z; R₆ est un groupe OR₁₆; R₇ et R₈ sont H, ou un atome d'halogène, ceci sous l'angle de leur utilisation en tant que modulateurs de l'activité du protéasome dans le cadre de la fabrication d'un médicament utile pour la prévention ou le traitement de maladies dans lesquelles le protéasome est impliqué, ou bien de compositions cosmétiques, ou bien encore de compositions phytosanitaires.