N-benzoyldehydrophenylalanyl glycine | 75667-05-9

• 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-benzoyldehydrophenylalanyl glycine
• 英文别名: 2-[(2-Benzamido-3-phenylprop-2-enoyl)amino]acetic acid
• CAS: 75667-05-9
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: QSACMLUENTXYHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzoyldehydrophenylalanyl glycine 、 N,N'-二环己基碳二亚胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 以64%的产率得到N-{2-[cyclohexyl(cyclohexylcarbamoyl)amino]-2-oxoethyl}-3-phenyl-2-(phenylformamido)prop-2-enamide
  参考文献：
  名称：

  Synthesis and biological evaluation of N-dehydrodipeptidyl-N,N′-dicyclohexylurea analogs

  摘要：

  Some N-[(N-benzoyldehydrophenylalalnyl)glycinyl/cysteinyl]-N,N'-dicyclohexylurea analogs (3a-3o) were synthesized by conjugating different substituted N-benzoyldehydrophenylalanyl glycines/cysteines (differing substitutions on benzylidene ring) and dicyclohexyl carbodiimide (DCC) using base as a catalyst. The synthesized compounds were characterized and evaluated for biological activities. Compounds 3a and 3h with unsubstituted dehydrophenylalanyl glycinyl/cysteinyl moiety exhibited moderate anti-inflammatory and analgesic activities. Compound 3j bearing 4-hydroxy substitution on benzylidene ring of dehydrophenylalanyl cysteinyl moiety displayed potent antimicrobial and antioxidant activities. The results obtained from docking studies on compound 3j with penicillin binding protein and protease supported the results. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.037
• 作为产物：
  描述：

  4-benzylidene-2-phenyloxazole-5(4H)-one 、 聚甘氨酸 在 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 N-benzoyldehydrophenylalanyl glycine
  参考文献：
  名称：

  Synthesis and biological evaluation of N-dehydrodipeptidyl-N,N′-dicyclohexylurea analogs

  摘要：

  Some N-[(N-benzoyldehydrophenylalalnyl)glycinyl/cysteinyl]-N,N'-dicyclohexylurea analogs (3a-3o) were synthesized by conjugating different substituted N-benzoyldehydrophenylalanyl glycines/cysteines (differing substitutions on benzylidene ring) and dicyclohexyl carbodiimide (DCC) using base as a catalyst. The synthesized compounds were characterized and evaluated for biological activities. Compounds 3a and 3h with unsubstituted dehydrophenylalanyl glycinyl/cysteinyl moiety exhibited moderate anti-inflammatory and analgesic activities. Compound 3j bearing 4-hydroxy substitution on benzylidene ring of dehydrophenylalanyl cysteinyl moiety displayed potent antimicrobial and antioxidant activities. The results obtained from docking studies on compound 3j with penicillin binding protein and protease supported the results. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.037

文献信息

• Synthesis and biological evaluation of N-dehydrodipeptidyl-N,N′-dicyclohexylurea analogs
  作者：B. Haseena banu、K.V.S.R.G. Prasad、K. Bharathi

  DOI：10.1016/j.ejmech.2014.03.037

  日期：2014.5

  Some N-[(N-benzoyldehydrophenylalalnyl)glycinyl/cysteinyl]-N,N'-dicyclohexylurea analogs (3a-3o) were synthesized by conjugating different substituted N-benzoyldehydrophenylalanyl glycines/cysteines (differing substitutions on benzylidene ring) and dicyclohexyl carbodiimide (DCC) using base as a catalyst. The synthesized compounds were characterized and evaluated for biological activities. Compounds 3a and 3h with unsubstituted dehydrophenylalanyl glycinyl/cysteinyl moiety exhibited moderate anti-inflammatory and analgesic activities. Compound 3j bearing 4-hydroxy substitution on benzylidene ring of dehydrophenylalanyl cysteinyl moiety displayed potent antimicrobial and antioxidant activities. The results obtained from docking studies on compound 3j with penicillin binding protein and protease supported the results. (C) 2014 Elsevier Masson SAS. All rights reserved.