(9H-fluoren-9-yl)methyl (S)-1-((S)-1-hydroxy-3-phenylpropan-2-ylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate | 1198108-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (9H-fluoren-9-yl)methyl (S)-1-((S)-1-hydroxy-3-phenylpropan-2-ylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate
• 英文别名: N-Fmoc-L-Trp-L-phenylalaninol；Fmoc-Trp-Phe-ol；9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamate
• CAS: 1198108-35-8
• 化学式: C₃₅H₃₃N₃O₄
• 分子量: 559.665
• InChiKey: ZAHZPIJEVUKLOA-JQJBXXCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (S)-1-((S)-1-hydroxy-3-phenylpropan-2-ylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate 、 苯甲酸酐 在 吡啶 作用下， 反应 6.0h， 以64%的产率得到(S)-2-((S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(1H-indol-3-yl)propanamido)-3-phenylpropyl benzoate
  参考文献：
  名称：

  Cytotoxic N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides: Structure–activity relationships and synergistic studies

  摘要：

  The synthesis and cytotoxic evaluation of a series of Fmoc-based dipeptides are described. Among the thirty compounds, 4a, 8a, 12a, 2b, 4b, 10b, 3c, 4c and 6c showed potent activity against HepG2, Hep3B, MCF-7, MDA-MB-231, A549 and Ca9-22 human cancer cell lines. The most active compounds (10a and 10c) showed relatively good sensitivity toward HepG2 and Ca9-22 cell lines with IC(50) values of 1 0 and 0 4 mu M, respectively. Additionally, compound 10c was threefold more potent than doxorubicin, the positive control, against the Ca9-22 cell line. Furthermore, 10c showed a synergistic effect and increased the cytotoxicity of doxorubicin against the MDA-MB-231 cancer cell line. Therefore, 10c could be used as a new lead compound for therapeutic development.

  DOI：

  10.1016/j.ejmech.2010.02.035
• 作为产物：
  描述：

  L-苯丙氨醇 、 Fmoc-L-色氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以53%的产率得到(9H-fluoren-9-yl)methyl (S)-1-((S)-1-hydroxy-3-phenylpropan-2-ylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamate
  参考文献：
  名称：

  Cytotoxic N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides: Structure–activity relationships and synergistic studies

  摘要：

  The synthesis and cytotoxic evaluation of a series of Fmoc-based dipeptides are described. Among the thirty compounds, 4a, 8a, 12a, 2b, 4b, 10b, 3c, 4c and 6c showed potent activity against HepG2, Hep3B, MCF-7, MDA-MB-231, A549 and Ca9-22 human cancer cell lines. The most active compounds (10a and 10c) showed relatively good sensitivity toward HepG2 and Ca9-22 cell lines with IC(50) values of 1 0 and 0 4 mu M, respectively. Additionally, compound 10c was threefold more potent than doxorubicin, the positive control, against the Ca9-22 cell line. Furthermore, 10c showed a synergistic effect and increased the cytotoxicity of doxorubicin against the MDA-MB-231 cancer cell line. Therefore, 10c could be used as a new lead compound for therapeutic development.

  DOI：

  10.1016/j.ejmech.2010.02.035

文献信息

• An efficient method for the preparation of peptide alcohols
  作者：Alan Roy Katritzky、Nader Elmaghwry Abo-Dya、Srinivasa Rao Tala、Kapil Gyanda、Zakaria Kamel Abdel-Samii

  DOI：10.1039/b905730g

  日期：——

  N -Protected LL-dipeptide alcohols 3a–p, diastereomeric mixture (3d + 3d′) and tripeptide alcohols 6a–c were synthesized by treatment of various amino alcohols with N-protected(α-aminoacyl)benzotriazoles 1a–c, 1f–m, (1a + 1a′) and N-protected(α-dipeptidoyl)benzotriazoles 5a, 5b respectively in good yields with complete retention of chirality.

  氮 -通过用N-保护的(α-氨基酰基)苯并三唑1a-c、1f-m处理各种氨基醇合成受保护的LL-二肽醇3a-p、非对映体混合物(3d + 3d')和三肽醇6a-c， (1a + 1a') 和 N-保护的(α-二肽酰基)苯并三唑 5a、5b 分别具有良好的产率，并且完全保留了手性。
• Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents
  作者：Chiao-Ting Yen、Tsong-Long Hwang、Yang-Chang Wu、Pei-Wen Hsieh

  DOI：10.1016/j.ejmech.2008.11.008

  日期：2009.5

  Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9,12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8+/-0.1 and 1.7+/-0.6 mu M, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead antiinflammatory agents. (C) 2008 Elsevier Masson SAS. All rights reserved.
• AURANTIAMIDE DIPEPTIDE DERIVATIVES FOR TREATMENT OR PREVENTION OF ANGIOGENESIS-RELATED DISEASES
  申请人：Mackay Medical College

  公开号：US20170182114A1

  公开（公告）日：2017-06-29

  The invention relates to a use of an aurantiamide dipepetide derivative in the treatment or prevention of angiogenesis-related diseases. Accordingly, aurantiamide dipeptide derivatives can be used as angiogenesis inhibitor, whereby preventing or treating invasive and metastatic cancer and ocular neovascularization (particularly macular degeneration such as pathological neovascularization of age-related macular degeneration (AMD)).
• US9872882B2
  申请人：——

  公开号：US9872882B2

  公开（公告）日：2018-01-23
• Cytotoxic N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides: Structure–activity relationships and synergistic studies
  作者：Chiao-Ting Yen、Chin-Chung Wu、Jin-Ching Lee、Shu-Li Chen、Susan L. Morris-Natschke、Pei-Wen Hsieh、Yang-Chang Wu

  DOI：10.1016/j.ejmech.2010.02.035

  日期：2010.6

  The synthesis and cytotoxic evaluation of a series of Fmoc-based dipeptides are described. Among the thirty compounds, 4a, 8a, 12a, 2b, 4b, 10b, 3c, 4c and 6c showed potent activity against HepG2, Hep3B, MCF-7, MDA-MB-231, A549 and Ca9-22 human cancer cell lines. The most active compounds (10a and 10c) showed relatively good sensitivity toward HepG2 and Ca9-22 cell lines with IC(50) values of 1 0 and 0 4 mu M, respectively. Additionally, compound 10c was threefold more potent than doxorubicin, the positive control, against the Ca9-22 cell line. Furthermore, 10c showed a synergistic effect and increased the cytotoxicity of doxorubicin against the MDA-MB-231 cancer cell line. Therefore, 10c could be used as a new lead compound for therapeutic development.