benzyl (S)-N-[2-(1H-indol-3-yl)-1-phenylcarbamoylethyl]carbamate | 158951-61-2

• 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: benzyl (S)-N-[2-(1H-indol-3-yl)-1-phenylcarbamoylethyl]carbamate
• 英文别名: Z-Trp-NHPh；N^α-benzyloxycarbonyl-L-tryptophan-anilide；N^α-Benzyloxycarbonyl-L-tryptophan-anilid；benzyl N-[(2S)-1-anilino-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
• CAS: 158951-61-2
• 化学式: C₂₅H₂₃N₃O₃
• mdl: MFCD02226207
• 分子量: 413.476
• InChiKey: QSWFNHDSWMFZHJ-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (S)-N-[2-(1H-indol-3-yl)-1-phenylcarbamoylethyl]carbamate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 以88%的产率得到(S)-2-amino-3-(1H-indol-3-yl)-N-phenylpropanamide
  参考文献：
  名称：

  Organocatalysis of asymmetric aldol reaction in water: comparison of catalytic properties of (S)-valine and (S)-proline amides

  摘要：

  含有在N1原子上带有(S)-或(R)-α-苯乙基取代基的(S)-缬氨酰胺，能高效催化水中环状（杂环）酮与芳香醛的不对称Aldol反应，主要生成高产率（高达98%）和高对映体过量（高达94%）的Aldol反式异构体。

  DOI：

  10.1007/s11172-013-0132-z
• 作为产物：
  描述：

  苯胺 、 N-苄氧羰基-L-色氨酸 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.75h， 以70%的产率得到benzyl (S)-N-[2-(1H-indol-3-yl)-1-phenylcarbamoylethyl]carbamate
  参考文献：
  名称：

  Organocatalysis of asymmetric aldol reaction in water: comparison of catalytic properties of (S)-valine and (S)-proline amides

  摘要：

  含有在N1原子上带有(S)-或(R)-α-苯乙基取代基的(S)-缬氨酰胺，能高效催化水中环状（杂环）酮与芳香醛的不对称Aldol反应，主要生成高产率（高达98%）和高对映体过量（高达94%）的Aldol反式异构体。

  DOI：

  10.1007/s11172-013-0132-z

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。
• Compounds useful as modulators of the proteasome activity
  申请人：Centre National de la Recherche Scientifique (C.N.R.S.)

  公开号：US07919468B2

  公开（公告）日：2011-04-05

  Compounds of the following general formula (I): are provided. The compounds can be used as modulators of the proteasome activity, in the preparation of a medicament useful for the prevention or treatment of diseases wherein the proteasome is involved, such as diseases of inflammatory processes, various hematological and solid tumor cancers, immunological and autoimmune diseases, cardiac pathologies, myopathies, AIDS, cystic fibrosis, Alzheimer's and Parkinson's disease, or in the preparation of cosmetic compositions or phytosanitary compositions.

  提供了以下一般式（I）的化合物。这些化合物可用作蛋白酶体活性的调节剂，用于制备有用于预防或治疗蛋白酶体参与的疾病的药物，如炎症过程疾病、各种血液和实体肿瘤癌症、免疫和自身免疫性疾病、心脏病理学、肌病、艾滋病、囊性纤维化、阿尔茨海默病和帕金森病，或用于制备化妆品组合物或植物保护组合物。
• Hanson; Smith, Journal of Biological Chemistry, 1949, vol. 179, p. 815,817
  作者：Hanson、Smith

  DOI：——

  日期：——
• WO2006/105811
  申请人：——

  公开号：——

  公开（公告）日：——
• Linear TMC-95-Based Proteasome Inhibitors
  作者：Nicolas Basse、Sandrine Piguel、David Papapostolou、Alexandra Ferrier-Berthelot、Nicolas Richy、Maurice Pagano、Pierre Sarthou、Joëlle Sobczak-Thépot、Michèle Reboud-Ravaux、Joëlle Vidal

  DOI：10.1021/jm0701324

  日期：2007.6.1

  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.