ethyl 2-[[2-[[2-[[2-[[5-nitro-2-(phenoxymethyl)benzoyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetate | 129229-80-7

• 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: ethyl 2-[[2-[[2-[[2-[[5-nitro-2-(phenoxymethyl)benzoyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetate
• CAS: 129229-80-7
• 化学式: C₂₄H₂₇N₅O₉
• 分子量: 529.506
• InChiKey: NJWOAHXWMYXDIX-UHFFFAOYSA-N

物化性质

• 熔点：
  197-200 °C
• 沸点：
  874.3±65.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  195.07
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[[2-[[2-[[2-[[5-nitro-2-(phenoxymethyl)benzoyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetate 在 platinum(IV) oxide 盐酸 、 氢溴酸 、 氢气 、 一水合肼 、 N,N-二异丙基乙胺 、 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 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 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 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 、 甲基三辛基氯化铵 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 ethyl 2-[[2-[[2-[[2-[[5-nitro-2-(phenoxymethyl)benzoyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]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

文献信息

• Specific and Irreversible Cyclopeptide Inhibitors of Dipeptidyl Peptidase IV Activity of the T-Cell Activation Antigen CD26
  作者：Coralie Nguyen、Julià Blanco、Jean-Paul Mazaleyrat、Bernard Krust、Christian Callebaut、Etienne Jacotot、Ara G. Hovanessian、Michel Wakselman

  DOI：10.1021/jm970640l

  日期：1998.6.1

  lysine in the P2 position, which allows the closing of the cycle on its side chain. These molecules show a free N-terminus, necessary for binding to the CD26 catalytic site, and a latent quinoniminium methide electrophile, responsible for inactivation. Treatment of c[alphaZ-Lys-Pro-Aba-(6-CH2-OC6H5)-Glyn], obtained by peptide synthesis in solution, with R2S/TFA simutaneously cleaved the Z protecting group

  CD26的二肽基肽酶IV（DPP IV）活性的特征在于其脯氨酸后裂解能力，该能力在生物过程中起着重要但尚未理解的作用。在这里，我们描述了该酶的特异性和不可逆抑制剂的新家族。考虑到DPP IV对P2-P1>-P1'裂解的底物特异性，我们设计并合成了环肽c [（alphaH2N +）-Lys-Pro-Aba-（6-CH2-S + R2）-Glyn] 2TFA-（Aba = 3-氨基苯甲酸，R =烷基）在P1位置具有脯氨酸，在P2位置具有赖氨酸，从而可以封闭侧链上的环。这些分子显示出一个自由的N端（对与CD26催化位点结合必不可少），以及一个潜在的灭活的甲基喹啉min亲电体。c [alphaZ-Lys-Pro-Aba-（6- -OC6H5）-Glyn]的治疗，通过在溶液中通过肽合成获得的产物，与R2S / TFA同时裂解Z保护基和苯基醚官能团，并生成一系列环肽sulf盐。这些环肽迅速且不可逆地抑制CD26的DPP
• Bogetto, Nicole; Vilain, Anne-Cecile; Montagne, Jean-Jacques, Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 152 - 166
  作者：Bogetto, Nicole、Vilain, Anne-Cecile、Montagne, Jean-Jacques、Reboud-Ravaux, Michele、Mazaleyrat, Jean-Paul、et al.

  DOI：——

  日期：——
• Xie, J.; Mazaleyrat, J. P.; Savrda, J., Bulletin de la Societe Chimique de France, 1992, # 6, p. 642 - 654
  作者：Xie, J.、Mazaleyrat, J. P.、Savrda, J.、Wakselman, M.

  DOI：——

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

  DOI：——

  日期：——