N²-benzyloxycarbonyl-N¹-phenyl-L-isoglutamine | 198134-01-9

• 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: N²-benzyloxycarbonyl-N¹-phenyl-L-isoglutamine
• 英文别名: N-Benzyloxycarbonyl-L-glutaminsaeure-1-anilid；N¹-Phenyl-N²-benzyloxycarbonyl-L-isoglutamin；(4S)-5-anilino-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 198134-01-9
• 化学式: C₁₉H₂₀N₂O₅
• 分子量: 356.378
• InChiKey: VJUSARPNXQOBGI-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N²-benzyloxycarbonyl-N¹-phenyl-L-isoglutamine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (4S)-4-铵基-5-苯胺基-5-氧代戊酸酯
  参考文献：
  名称：

  Zur Aktivität und Spezifität der Leucinaminopeptidase in Augenlinsen. Aminosäure- und Dipeptidanilide als Substrate

  摘要：

  DOI：

  10.1515/bchm2.1960.322.1.101
• 作为产物：
  描述：

  苯胺 、 N-苄氧羰基-L-谷氨酸酐 以 苯 为溶剂， 反应 0.33h， 以98%的产率得到N²-benzyloxycarbonyl-N¹-phenyl-L-isoglutamine
  参考文献：
  名称：

  Controlled Regioselective Anilide Formation from Aspartic and Glutamic Acid Anhydrides

  摘要：

  The regioselectivity of the reaction of aniline with a series of N-protected aspartic and glutamic acid anhydrides was controlled through the choice of reaction solvent. In benzene, the formation of aspartic or glutamic acid a-anilides was favored, with alpha:(beta or gamma) regioselectivities as high as 100:0. On the other hand, in DMSO, the formation of either aspartic acid beta-anilide or glutamic acid gamma-anilide was favored, with alpha:(beta or gamma) regioselectivities as high as 0:100. This regioselectivity was not observed for alkylamines, amino acids, thiols, or alcohols. However, the high yields of the aniline reactions and the ability to specify their regioselectivities demonstrate the usefulness of our method for the formation of aspartic and glutamic acid anilide bonds.

  DOI：

  10.1021/jo971375e

文献信息

• [EN] PEPTIDOMIMETIC INHIBITORS OF Β-CATENIN/TCF PROTEIN–PROTEIN INTERACTION<br/>[FR] INHIBITEURS PEPTIDOMIMÉTIQUES DE L'INTERACTION PROTÉINE-PROTÉINE B-CATÉNINE/TCF
  申请人：H LEE MOFFITT CANCER CT & RES

  公开号：WO2020118179A1

  公开（公告）日：2020-06-11

  Disclosed are inhibitors for the β-catenin/T-cell factor interaction. The inhibitors are selective for β-catenin/T-cell factor over β-catenin/phosphocadherin, and β- catenin/phosphoAPC interactions. Methods of using the disclosed compounds to treat cancer are also disclosed.

  披露了β-连环蛋白/ T细胞因子相互作用的抑制剂。这些抑制剂对β-连环蛋白/ T细胞因子相互作用具有选择性，而不影响β-连环蛋白/磷酸钙粘蛋白和β-连环蛋白/磷酸化APC相互作用。还披露了利用这些披露的化合物治疗癌症的方法。
• 535. Peptide synthesis from heterocyclic intermediates. Part I. 2-Thio-5-thiazolidone derivatives of valine, leucine, norleucine, methionine, l-tyrosine, glutamine, αaminoisobutyric acid, and aminomalonamide
  作者：A. C. Davis、A. L. Levy

  DOI：10.1039/jr9510002419

  日期：——
• Behrens; Bergmann, Journal of Biological Chemistry, 1939, vol. 129, p. 587,593
  作者：Behrens、Bergmann

  DOI：——

  日期：——
• Edelson et al., Journal of medicinal and pharmaceutical chemistry, 1959, vol. 1, p. 165,167
  作者：Edelson et al.

  DOI：——

  日期：——
• PEPTIDOMIMETIC INHIBITORS OF B-CATENIN/TCF PROTEIN-PROTEIN INTERACTION
  申请人：H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.

  公开号：US20220024977A1

  公开（公告）日：2022-01-27

  Disclosed are inhibitors for the β-catenin/T-cell factor interaction. The inhibitors are selective for β-catenin/T-cell factor over β-catenin/phosphocadherin, and β-catenin/phosphoAPC interactions. Methods of using the disclosed compounds to treat cancer are also disclosed.