(4S)-4-benzyl-20-(chloromethyl)-2,5,8,11,14,17-hexazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexone | 129229-68-1

• 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: (4S)-4-benzyl-20-(chloromethyl)-2,5,8,11,14,17-hexazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexone
• CAS: 129229-68-1
• 化学式: C₂₅H₂₇ClN₆O₆
• 分子量: 542.979
• InChiKey: HQGJTHJLPUYBFD-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(4S)-4-benzyl-3,6,9,12,15,18-hexaoxo-2,5,8,11,14,17-hexazabicyclo[17.3.1]tricosa-1(23),19,21-trien-20-yl]methyl acetate 在 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.07h， 生成 (4S)-4-benzyl-20-(chloromethyl)-2,5,8,11,14,17-hexazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexone
  参考文献：
  名称：

  Cyclopeptidic inactivators for chymotrypsin-like proteinases

  摘要：

  Cyclopeptides containing a functionalized meta-aminobenzoic acid residue (m-aB[CH2X] with X = OC6H5, OAc, Br, Cl) linked to a tetraglycyl-phenylalanyl sequence, have been synthesized in solution. A phenyl ether group has been used during chain elongation and cyclisation, and then cleaved by treatment with HBr/HOAc to give the corresponding bromide, from which the acetate and the chloride have been obtained. The functionalized aminobenzoic acid residues possess a latent quinonimmonium methide electrophilic function, and these cyclopeptides are potential ''suicide'' substrates of chymotrypsin-like proteases. The cyclopeptides with X = Br or Cl irreversibly inhibit alpha-chymotrypsin (k(inact)/K(I) = 180 M-1min-1 for X = Cl). The compounds with poorer leaving groups X = OAc or OC6H5 are devoid of inactivating effect and only behave as substrates of this enzyme (k(cat)/K(M) = 31 800 M-1min-1 and 120 000 M-1min-1, respectively).

  DOI：

  10.1016/0223-5234(91)90119-8

文献信息

• WAKSELMAN, MICHEL;MAZALEYRAT, JEAN-PAUL;REBOUD, MICHELE
  作者：WAKSELMAN, MICHEL、MAZALEYRAT, JEAN-PAUL、REBOUD, MICHELE

  DOI：——

  日期：——