N-acetyl-O-(N'-tert-butoxycarbonyl-L-phenylalanyl)-L-phenylalaninol | 1229046-61-0

• 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: N-acetyl-O-(N'-tert-butoxycarbonyl-L-phenylalanyl)-L-phenylalaninol
• 英文别名: [(2S)-2-acetamido-3-phenylpropyl] (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 1229046-61-0
• 化学式: C₂₅H₃₂N₂O₅
• 分子量: 440.539
• InChiKey: PHUMHBRKVZCHRQ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetyl-O-(N'-tert-butoxycarbonyl-L-phenylalanyl)-L-phenylalaninol 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (S)-2-acetamido-3-phenylpropyl L-phenylalaninate
  参考文献：
  名称：

  Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine

  摘要：

  All stereoisomers of asperphenamate 1a and patriscabratine 2a were achieved with a high yield, and total synthesis of 2a is firstly described here. The absolute configuration of patriscabratine was determined as (S,S). The compounds 1a-d and 2a-d have been tested by MTT assay in T47D, MDA-MB231, HL60, Hela and SGC-7901 cell lines in vitro. Among them, the (R,S) stereoisomer shows the strongest anticancer effects, while the (S,R) shows the weakest one. (C) 2009 Tie Min Sun. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2009.10.004
• 作为产物：
  描述：

  L-苯丙氨酸 在 sodium tetrahydroborate 、 硫酸 、 碘 、 potassium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 生成 N-acetyl-O-(N'-tert-butoxycarbonyl-L-phenylalanyl)-L-phenylalaninol
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of asperphenamate derivatives as autophagy inducer

  摘要：

  In an effort to improve the aqueous solubility and the antitumor activity of natural product asperphenamate, we have designed and synthesized three series of asperphenamate derivatives, including series I (simplifying molecular skeleton series), series II (introducing a hydroxyl group to A-phenyl ring series) and series III (disrupting molecular planarity series). All derivatives have displayed a significantly increased solubility compared with asperphenamate. Their growth inhibitory activities in vitro were screened by the standard MTT method in MCF-7, HeLa, and BEL-7402 cell lines. With the exception of the derivatives in series I, most of derivatives in series II and series III showed growth inhibitory activity. Among all derivatives, IM23b in series III showed the greatest potency in human breast cancer MCF-7 cells. The cellular potency of IM23b was approximately 1.5-fold more potent than that of cisplatin. The mechanism of cell death induced by IM23b in human breast cancer MCF-7 cells was further investigated. We concluded that the cell death was induced by autophagy instead of apoptosis or cell cycle arrest. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.101

文献信息

• Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine
  作者：Lei Yuan、Jin Hui Wang、Tie Min Sun

  DOI：10.1016/j.cclet.2009.10.004

  日期：2010.2

  All stereoisomers of asperphenamate 1a and patriscabratine 2a were achieved with a high yield, and total synthesis of 2a is firstly described here. The absolute configuration of patriscabratine was determined as (S,S). The compounds 1a-d and 2a-d have been tested by MTT assay in T47D, MDA-MB231, HL60, Hela and SGC-7901 cell lines in vitro. Among them, the (R,S) stereoisomer shows the strongest anticancer effects, while the (S,R) shows the weakest one. (C) 2009 Tie Min Sun. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Synthesis and in vitro antitumor activity of asperphenamate derivatives as autophagy inducer
  作者：Lei Yuan、Yanchun Li、Chunyang Zou、Chao Wang、Jian Gao、Caixia Miao、Enlong Ma、Tiemin Sun

  DOI：10.1016/j.bmcl.2012.01.101

  日期：2012.3

  In an effort to improve the aqueous solubility and the antitumor activity of natural product asperphenamate, we have designed and synthesized three series of asperphenamate derivatives, including series I (simplifying molecular skeleton series), series II (introducing a hydroxyl group to A-phenyl ring series) and series III (disrupting molecular planarity series). All derivatives have displayed a significantly increased solubility compared with asperphenamate. Their growth inhibitory activities in vitro were screened by the standard MTT method in MCF-7, HeLa, and BEL-7402 cell lines. With the exception of the derivatives in series I, most of derivatives in series II and series III showed growth inhibitory activity. Among all derivatives, IM23b in series III showed the greatest potency in human breast cancer MCF-7 cells. The cellular potency of IM23b was approximately 1.5-fold more potent than that of cisplatin. The mechanism of cell death induced by IM23b in human breast cancer MCF-7 cells was further investigated. We concluded that the cell death was induced by autophagy instead of apoptosis or cell cycle arrest. (C) 2012 Elsevier Ltd. All rights reserved.