Boc-L-Phe-L-N-(Me)Phe-L-Val-L-N-(Me)Phe-OMe | 1173659-19-2

• 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: Boc-L-Phe-L-N-(Me)Phe-L-Val-L-N-(Me)Phe-OMe
• 英文别名: Boc-Phe-N(Me)Phe-Val-N(Me)Phe-OMe；methyl (2S)-2-[methyl-[(2S)-3-methyl-2-[[(2S)-2-[methyl-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]butanoyl]amino]-3-phenylpropanoate
• CAS: 1173659-19-2
• 化学式: C₄₀H₅₂N₄O₇
• 分子量: 700.875
• InChiKey: UYAYENKOTXEMST-CUPIEXAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  51
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-L-Phe-L-N-(Me)Phe-L-Val-L-N-(Me)Phe-OMe 在 sodium hydroxide 、 水 作用下， 反应 1.0h， 生成 Boc-L-Phe-L-N-(Me)Phe-L-Val-L-N-(Me)Phe-OH
  参考文献：
  名称：

  Toward the synthesis and biological evaluation of hirsutide

  摘要：

  The present investigation deals with the synthesis of a N-methylated cyclotetrapeptide, hirsutide (2), by coupling of the dipeptide units Boc-L-phenylalanyl-L-N-methylphenylalanine-OH and L-valyl-L-N-methylphenylalanine-OMe followed by cyclization of the linear tetrapeptide fragment. The chemical structure was established on the basis of analytical as well as spectroscopic data. The newly synthesized cyclic peptide was subjected to pharmacological screening and found to be highly potent against the gram-negative bacteria Pseudomonas aeruginosa and Klebsiella pneumoniae at 6 mu g cm(-3). In addition, potent antihelmintic activity against the earthworms Megascoplex konkanensis and Pontoscotex corethruses at 1 and 2 mg cm(-3), and potent cytotoxic activity against Dalton's lymphoma ascites and Ehrlich's ascites carcinoma cell lines with IC50 values of 14 and 22 mu M were also observed. Studies revealed that the pentafluorophenyl ester method employing a catalytic amount of N-methylmorpholine proved to be better for cyclization of the linear tetrapeptide unit.

  DOI：

  10.1007/s00706-008-0052-z
• 作为产物：
  描述：

  Boc-L-phenylalanyl-L-N-methylphenylalanine-OMe 、 N-t-Boc-L-Phe-L-Phe(N^α-Me)-OH 在 N-甲基吗啉 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以84%的产率得到Boc-L-Phe-L-N-(Me)Phe-L-Val-L-N-(Me)Phe-OMe
  参考文献：
  名称：

  Toward the synthesis and biological evaluation of hirsutide

  摘要：

  The present investigation deals with the synthesis of a N-methylated cyclotetrapeptide, hirsutide (2), by coupling of the dipeptide units Boc-L-phenylalanyl-L-N-methylphenylalanine-OH and L-valyl-L-N-methylphenylalanine-OMe followed by cyclization of the linear tetrapeptide fragment. The chemical structure was established on the basis of analytical as well as spectroscopic data. The newly synthesized cyclic peptide was subjected to pharmacological screening and found to be highly potent against the gram-negative bacteria Pseudomonas aeruginosa and Klebsiella pneumoniae at 6 mu g cm(-3). In addition, potent antihelmintic activity against the earthworms Megascoplex konkanensis and Pontoscotex corethruses at 1 and 2 mg cm(-3), and potent cytotoxic activity against Dalton's lymphoma ascites and Ehrlich's ascites carcinoma cell lines with IC50 values of 14 and 22 mu M were also observed. Studies revealed that the pentafluorophenyl ester method employing a catalytic amount of N-methylmorpholine proved to be better for cyclization of the linear tetrapeptide unit.

  DOI：

  10.1007/s00706-008-0052-z

文献信息

• Toward the synthesis and biological evaluation of hirsutide
  作者：Rajiv Dahiya、Monika Maheshwari、Anil Kumar

  DOI：10.1007/s00706-008-0052-z

  日期：2009.1

  The present investigation deals with the synthesis of a N-methylated cyclotetrapeptide, hirsutide (2), by coupling of the dipeptide units Boc-L-phenylalanyl-L-N-methylphenylalanine-OH and L-valyl-L-N-methylphenylalanine-OMe followed by cyclization of the linear tetrapeptide fragment. The chemical structure was established on the basis of analytical as well as spectroscopic data. The newly synthesized cyclic peptide was subjected to pharmacological screening and found to be highly potent against the gram-negative bacteria Pseudomonas aeruginosa and Klebsiella pneumoniae at 6 mu g cm(-3). In addition, potent antihelmintic activity against the earthworms Megascoplex konkanensis and Pontoscotex corethruses at 1 and 2 mg cm(-3), and potent cytotoxic activity against Dalton's lymphoma ascites and Ehrlich's ascites carcinoma cell lines with IC50 values of 14 and 22 mu M were also observed. Studies revealed that the pentafluorophenyl ester method employing a catalytic amount of N-methylmorpholine proved to be better for cyclization of the linear tetrapeptide unit.