[Tyr-5-ψ(CH2NMe)-Tyr-6]RA-VII | 1372157-31-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: [Tyr-5-ψ(CH2NMe)-Tyr-6]RA-VII
• 英文别名: (1S,4R,7S,10S,13S,16S)-24-methoxy-10-[(4-methoxyphenyl)methyl]-4,7,9,13,15,29-hexamethyl-22-oxa-3,6,9,12,15,29-hexazatetracyclo[14.12.2.218,21.123,27]tritriaconta-18,20,23,25,27(31),32-hexaene-2,5,8,11,14-pentone
• CAS: 1372157-31-7
• 化学式: C₄₁H₅₂N₆O₈
• 分子量: 756.899
• InChiKey: FLWGIXONJICRAN-IEBFUVSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  55
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (9S,12S)-12-(tert-Butoxycarbonyl-methyl-amino)-4-methoxy-10-methyl-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1(17),3(19),4,6,14(18),15-hexaene-9-carboxylic acid benzyl ester 在 盐酸 、 硼烷四氢呋喃络合物 、 5%-palladium/activated carbon 、 五氟苯基二苯基磷酸酯 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 [Tyr-5-ψ(CH2NMe)-Tyr-6]RA-VII
  参考文献：
  名称：

  Synthesis of [Tyr-5-Ψ(CH2NMe)-Tyr-6]RA-VII, a reduced peptide bond analogue of RA-VII, an antitumor bicyclic hexapeptide

  摘要：

  A reduced peptide bond analogue of RA-VII, [Tyr-5-Psi(CH2NMe)-Tyr-6]RA-VII (3), was designed and synthesized. The key reduced cycloisodityrosine unit was prepared by reduction of the cycloisodityrosine derived from natural RA-VII, followed by connection with the tetrapeptide segment to afford a hexapeptide. Subsequent macrocyclization of the hexapeptide with FDPP under dilute conditions gave 3. Analogue 3 showed cytotoxic activity against P-388 cells, but its activity was much weaker than that of parent peptide RA-VII. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.093

文献信息

• Synthesis of [Tyr-5-Ψ(CH2NMe)-Tyr-6]RA-VII, a reduced peptide bond analogue of RA-VII, an antitumor bicyclic hexapeptide
  作者：Tomoyo Hasuda、Yukio Hitotsuyanagi、Mitsuyuki Shinada、Koichi Takeya

  DOI：10.1016/j.bmcl.2012.02.093

  日期：2012.4

  A reduced peptide bond analogue of RA-VII, [Tyr-5-Psi(CH2NMe)-Tyr-6]RA-VII (3), was designed and synthesized. The key reduced cycloisodityrosine unit was prepared by reduction of the cycloisodityrosine derived from natural RA-VII, followed by connection with the tetrapeptide segment to afford a hexapeptide. Subsequent macrocyclization of the hexapeptide with FDPP under dilute conditions gave 3. Analogue 3 showed cytotoxic activity against P-388 cells, but its activity was much weaker than that of parent peptide RA-VII. (C) 2012 Elsevier Ltd. All rights reserved.