N-(N-4-chloroacetamidobenzoyl-L-phenylalanyl)-L-phenylalanine methyl ester | 934221-30-4

• 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-(N-4-chloroacetamidobenzoyl-L-phenylalanyl)-L-phenylalanine methyl ester
• 英文别名: methyl N-[N-(4-chloroacetamido-benzoyl)-L-phenylalanyl]-L-phenylalaninate；Methyl (2S)-2-[[(2S)-2-[[4-[(2-chloroacetyl)amino]benzoyl]amino]-3-phenyl-propanoyl]amino]-3-phenyl-propanoate；methyl (2S)-2-[[(2S)-2-[[4-[(2-chloroacetyl)amino]benzoyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoate
• CAS: 934221-30-4
• 化学式: C₂₈H₂₈ClN₃O₅
• 分子量: 522.0
• InChiKey: OALSEKLZIBBNER-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(2-氯乙酰氨基)苯甲酸 在 N-甲基吗啉 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(N-4-chloroacetamidobenzoyl-L-phenylalanyl)-L-phenylalanine methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of Matijing-Su derivatives as potent anti-HBV agents

  摘要：

  A series of Matijing-Su (MTS, N-(N-benzoyl-L-phenylalanyl)-O-acetyl-L-phenylalanol) derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity in 2.2.15 cells. The IC50 of compounds 14a (0.71 mu M), 13c (2.85 mu M), 13b (4.37 mu M), etc. and the selective index of 13g (161.01), 13c (90.45), 13a (85.09) etc. of the inhibition on the replication of HBV DNA were better than those of the positive control lamivudine (IC50: 82.42 mu M, SI: 41.59). Compounds 13o, 13p, and 16a also exhibited significant anti-HBV activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.001

文献信息

• PHENYLALANINE DIPEPTIDE DERIVATIVES, COMPOSITIONS AND USE THEREOF
  申请人：Liang Guangyi

  公开号：US20090247470A1

  公开（公告）日：2009-10-01

  Disclosed are a compound of formula I, stereoisomers, pharmaceutically acceptable salts or hydrates thereof, a pharmaceutical composition comprising the smae, a process for preparing the same and use thereof. The compound may also be used to prepare a medicament to treat viral infections, especially to prepare a medicament to treat hepatitis B virus and human immunodeficiency virus with little toxic side effects.

  公开了一种具有I式化合物、立体异构体、药学上可接受的盐或水合物的化合物，包括该化合物的药物组合物，制备该化合物的方法以及其用途。该化合物还可用于制备治疗病毒感染的药物，特别是用于制备治疗乙型肝炎病毒和人类免疫缺陷病毒的药物，具有较小的毒副作用。
• US9023809B2
  申请人：——

  公开号：US9023809B2

  公开（公告）日：2015-05-05
• Synthesis and biological evaluation of Matijing-Su derivatives as potent anti-HBV agents
  作者：Jingying Qiu、Bixue Xu、Zhengming Huang、Weidong Pan、Peixue Cao、Changxiao Liu、Xiaojiang Hao、Baoan Song、Guangyi Liang

  DOI：10.1016/j.bmc.2011.08.001

  日期：2011.9

  A series of Matijing-Su (MTS, N-(N-benzoyl-L-phenylalanyl)-O-acetyl-L-phenylalanol) derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity in 2.2.15 cells. The IC50 of compounds 14a (0.71 mu M), 13c (2.85 mu M), 13b (4.37 mu M), etc. and the selective index of 13g (161.01), 13c (90.45), 13a (85.09) etc. of the inhibition on the replication of HBV DNA were better than those of the positive control lamivudine (IC50: 82.42 mu M, SI: 41.59). Compounds 13o, 13p, and 16a also exhibited significant anti-HBV activity. (C) 2011 Elsevier Ltd. All rights reserved.