N-(N-benzoyl-L-phenylalanyl)-L-tyrosine methyl ester | 60142-77-0

• 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-(N-benzoyl-L-phenylalanyl)-L-tyrosine methyl ester
• 英文别名: methyl N-(N-benzoyl-L-phenylalanyl)-L-tyrosinate；methyl N-benzoylphenylalanyltyrosinate；methyl (2S)-2-[[(2S)-2-benzamido-3-phenylpropanoyl]amino]-3-(4-hydroxyphenyl)propanoate
• CAS: 60142-77-0
• 化学式: C₂₆H₂₆N₂O₅
• 分子量: 446.503
• InChiKey: VAOTVDABLTUNEK-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N-benzoyl-L-phenylalanyl)-L-tyrosine methyl ester 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 sodium N-(N-benzoyl-L-phenylalanyl)-O-methyl-L-tyrosinate
  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
• 作为产物：
  描述：

  N-苯甲酰-L-苯丙氨酸甲酯 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 3.5h， 生成 N-(N-benzoyl-L-phenylalanyl)-L-tyrosine 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。
• Synthesis and anti-hepatitis B virus activities of Matijing-Su derivatives
  作者：Bixue Xu、Zhengming Huang、Changxiao Liu、Zegui Cai、Weidong Pan、Peixue Cao、Xiaojiang Hao、Guangyi Liang

  DOI：10.1016/j.bmc.2009.03.003

  日期：2009.4

  A series of derivatives of Matijing-Su (MTS, N-(N-benzoyl-l-phenylalanyl)-O-acetyl-l-phenylalanol) was synthesized and evaluated for their anti-hepatitis B virus (HBV) activities in 2.2.15 cells. The IC50 of compounds 9c (1.40 μM), 9g (2.33 μM) and 9n (2.36 μM), etc. and the selective index of 9n (45.93) of the inhibition on the replication of HBV DNA were higher than those of the positive control

  合成了Matijing-Su的一系列衍生物（MTS，N-（N-（N-苯甲酰基-1-苯丙氨酰基）-O-乙酰基-1-苯基丙醇），并在2.2.15中评估了其抗乙型肝炎病毒（HBV）的活性。细胞。化合物9c（1.40μM），9g（2.33μM）和9n（2.36μM）等的IC 50和9n（45.93）抑制HBV DNA复制的选择性指数高于阳性对照拉米夫定[41.59，（IC 50：82.42μM）]。化合物11d，12a和12e 也表现出显着的抗乙肝病毒活性。
• Tyrosine derivatives and use
  申请人：Daiichi Seiyaku Co., Ltd.

  公开号：US04025644A1

  公开（公告）日：1977-05-24

  Compounds having the formula: ##STR1## wherein R.sub.1 is phenyl or cycloalkyl and the phenyl may have at least one substituent selected from the group consisting of lower alkyl, lower alkoxy, amino and nitro; R.sub.2 is hydrogen or lower alkyl; A is --CH.sub.2 O-- or --CH.sub.2 CH(O-lower alkyl)-; n is zero or 1 when R.sub.1 together with (A).sub.n is unsubstituted phenyl, R.sub.2 is lower alkyl; and R.sub.3 is hydrogen or lower alkoxy, have anti-ulcerousaction.

  具有以下式子的化合物：##STR1## 其中R.sub.1是苯基或环烷基，苯基可以具有至少一个从较低烷基，较低烷氧基，氨基和硝基中选择的取代基; R.sub.2是氢或较低烷基; A是--CH.sub.2 O--或--CH.sub.2 CH(O-较低烷基)-; 当R.sub.1与(A).sub.n未取代的苯基时，n为零或1，R.sub.2为较低烷基; R.sub.3是氢或较低烷氧基，具有抗溃疡作用。
• Tyrosine derivatives and process for preparing the same
  申请人：Daiichi Seiyaku Co., Ltd.

  公开号：US04057629A1

  公开（公告）日：1977-11-08

  Compounds having the formula: ##STR1## wherein R.sub.1 is phenyl or cycloalkyl and the phenyl may have at least one substituent selected from the group consisting of lower alkyl, lower alkoxy, amino and nitro; R.sub.2 is hydrogen or lower alkyl; A is --CH.sub.2 O-- or --CH.sub.2 CH(O-lower alkyl)-; n is zero (0) or one (1); when R.sub.1 together with (A).sub.n is unsubstituted phenyl, R.sub.2 is lower alkyl; and R.sub.3 is hydrogen or lower alkoxy, have anti-ulcerousaction.

  化合物的化学式为：##STR1## 其中R.sub.1是苯基或环烷基，苯基可能具有至少一个选自下列群组的取代基，该群组包括低碳基，低氧基，氨基和硝基；R.sub.2是氢或低碳基；A是--CH.sub.2 O--或--CH.sub.2 CH(O-低碳基)-；n为零（0）或一（1）；当R.sub.1与（A).sub.n一起为未取代的苯基时，R.sub.2为低碳基；且R.sub.3为氢或低氧基，具有抗溃疡作用。
• Anti-ulcerous tyrosine derivatives
  申请人：Daiichi Seiyaku Co., Ltd.

  公开号：US04097608A1

  公开（公告）日：1978-06-27

  Compounds having the formula ##STR1## wherein R.sub.1 is phenyl or cycloalkyl and the phenyl may have at least one substituent selected from the group consisting of lower alkyl, lower alkoxy, amino and nitro; R.sub.2 is hydrogen or lower alkyl; A is --CH.sub.2 O-- or --CH.sub.2 CH(O-lower alkyl)-; n is zero (0) or one (1); when R.sub.1 together with (A).sub.n is unsubstituted phenyl, R.sub.2 is lower alkyl; and R.sub.3 is hydrogen or lower alkoxy, have anti-ulcerous action.

  具有以下化学式的化合物 ##STR1## 其中R.sub.1是苯基或环烷基，苯基可能具有至少一种取代基，所选自较低的烷基，较低的烷氧基，氨基和硝基的群；R.sub.2是氢或较低的烷基；A是--CH.sub.2 O--或--CH.sub.2 CH(O-较低烷基)-；n为零(0)或一(1)；当R.sub.1与(A).sub.n一起是未取代的苯基时，R.sub.2是较低的烷基；R.sub.3是氢或较低的烷氧基，具有抗溃疡作用。