(4S)-4-benzyl-20-(phenoxymethyl)-2,5,8,11,14,17-hexazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexone | 131918-93-9

• 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: (4S)-4-benzyl-20-(phenoxymethyl)-2,5,8,11,14,17-hexazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexone
• CAS: 131918-93-9
• 化学式: C₃₁H₃₂N₆O₇
• 分子量: 600.631
• InChiKey: LAPWQEARYNTBRM-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  44
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  184
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-20-(phenoxymethyl)-2,5,8,11,14,17-hexazabicyclo[17.3.1]tricosa-1(23),19,21-triene-3,6,9,12,15,18-hexone 在 氢溴酸 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 [(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
  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
• 作为产物：
  描述：

  2-甲基-5-硝基苯甲酸甲酯 在 platinum(IV) oxide 盐酸 、 氢氧化钾 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 过氧化氢苯甲酰 、 氢气 、 甲基三辛基氯化铵 、 一水合肼 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 N,N'-二环己基碳二亚胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 (4S)-4-benzyl-20-(phenoxymethyl)-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

• Cyclopeptidic inactivators for chymotrypsin-like proteinases
  作者：M Wakselman、JP Mazaleyrat、J Xie、JJ Montagne、AC Vilain、M Reboud-Ravaux

  DOI：10.1016/0223-5234(91)90119-8

  日期：1991.10

  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).