3-Amino-N-[2-(3,4-dioxo-cyclohexa-1,5-dienyl)-ethyl]-propionamide | 87838-85-5

• 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: 3-Amino-N-[2-(3,4-dioxo-cyclohexa-1,5-dienyl)-ethyl]-propionamide
• 英文别名: 3-amino-N-[2-(3,4-dioxocyclohexa-1,5-dien-1-yl)ethyl]propanamide
• CAS: 87838-85-5
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: JHIWMWSXOPCOKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  89.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  咪唑 、 3-Amino-N-[2-(3,4-dioxo-cyclohexa-1,5-dienyl)-ethyl]-propionamide 生成 3-Amino-N-[2-(4,5-dihydroxy-2-imidazol-1-yl-phenyl)-ethyl]-propionamide
  参考文献：
  名称：

  Model Insect Cuticle Sclerotization: Reactions of Catecholamine Quinones with the Nitrogen-Centered Nucleophiles Imidazole andN-Acetylhistidine

  摘要：

  The catecholamines N-acetyldopamine (NADA) and N-beta-alanyldopamine (NBAD) are two precursors for quinonoios used as sclerotizing agents in insect cuticle. This study focused on the reaction pathways of the quinones of NADA and NBAD by using two nitrogen-centered nucleophiles, imidazole and N-acetylhistidine, to model cuticular proteins containing histidyl residues. The quinones were prepared by electrochemical oxidation, using either a coulometric microcell or a how-through cell. The reactions of the quinones with the nucleophiles were investigated at physiological pH using electrochemical, chromatographic, and spectroscopic methods. The major products were purified by semipreparative Liquid chromatography and identified by mass spectrometry and nuclear magnetic resonance spectroscopy to be nucleophilic addition products of the quinones with the nucleophiles bonded to two carbons in the aromatic ring. The predominant products for both nucleophiles were C6 adducts of NADA and NBAD. C2 adducts of N-acetylhistidine were minor products. (C) 1997 Academic Press.

  DOI：

  10.1006/bioo.1997.1065
• 作为产物：
  描述：

  N(beta)-丙氨酰多巴胺 生成 3-Amino-N-[2-(3,4-dioxo-cyclohexa-1,5-dienyl)-ethyl]-propionamide
  参考文献：
  名称：

  5-S-谷胱甘肽-β-丙氨酰基-L-多巴类似物对Src蛋白酪氨酸激酶的选择性抑制。

  摘要：

  使用酪氨酸酶通过邻苯二酚合成了十二种抗菌酚肽5-S-谷胱甘肽-β-丙氨酰-L-多巴（5-S-GA-LD：1）。几种合成的化合物抑制v-Src自磷酸化酪氨酸激酶反应，其IC50值可与除草霉素相当。对c-Src底物磷酸化的抑制作用远小于对v-Src自磷酸化的抑制作用。这些类似物对表皮生长因子受体（EGFR）的底物磷酸化没有影响，这种选择性是该类似物的最典型特征（1-12）。

  DOI：

  10.1248/cpb.46.1950

文献信息

• Screening Test for Insecticides Interfering with Cuticular Sclerotization
  作者：Michael Londershausen、Andreas Turberg、Margarethe Spindler-Barth、Martin G. Peter

  DOI：10.1002/(sici)1096-9063(199612)48:4<315::aid-ps481>3.0.co;2-c

  日期：1996.12
• Model Insect Cuticle Sclerotization: Reactions of Catecholamine Quinones with the Nitrogen-Centered Nucleophiles Imidazole andN-Acetylhistidine
  作者：Xin Huang、Rongda Xu、M.Dale Hawley、Karl J. Kramer

  DOI：10.1006/bioo.1997.1065

  日期：1997.6

  The catecholamines N-acetyldopamine (NADA) and N-beta-alanyldopamine (NBAD) are two precursors for quinonoios used as sclerotizing agents in insect cuticle. This study focused on the reaction pathways of the quinones of NADA and NBAD by using two nitrogen-centered nucleophiles, imidazole and N-acetylhistidine, to model cuticular proteins containing histidyl residues. The quinones were prepared by electrochemical oxidation, using either a coulometric microcell or a how-through cell. The reactions of the quinones with the nucleophiles were investigated at physiological pH using electrochemical, chromatographic, and spectroscopic methods. The major products were purified by semipreparative Liquid chromatography and identified by mass spectrometry and nuclear magnetic resonance spectroscopy to be nucleophilic addition products of the quinones with the nucleophiles bonded to two carbons in the aromatic ring. The predominant products for both nucleophiles were C6 adducts of NADA and NBAD. C2 adducts of N-acetylhistidine were minor products. (C) 1997 Academic Press.
• Seiective Inhibition of Src Protein Tyrosine Kinase by Analogues of 5-S-Glutathionyl-.BETA.-alanyl-L-dopa.
  作者：Zhe-bin ZHENG、Sachie NAGAI、Naoko IWANAMI、Ayako KOBAYASHI、Mariko HIJIKATA、Shunji NATORI、Ushio SANKAWA

  DOI：10.1248/cpb.46.1950

  日期：——

  Twelve analogues of the antibacterial phenolic peptide 5-S-glutathionyl-beta-alanyl-L-dopa (5-S-GA-L-D: 1) were synthesized via orthoquinones using tyrosinase. Several synthesized compounds inhibited the v-Src autophosphorylation tyrosine kinase reaction with an IC50 value comparable to that of herbimycin. The inhibition of c-Src substrate phosphorylation was much less active than v-Src autophosphorylation

  使用酪氨酸酶通过邻苯二酚合成了十二种抗菌酚肽5-S-谷胱甘肽-β-丙氨酰-L-多巴（5-S-GA-LD：1）。几种合成的化合物抑制v-Src自磷酸化酪氨酸激酶反应，其IC50值可与除草霉素相当。对c-Src底物磷酸化的抑制作用远小于对v-Src自磷酸化的抑制作用。这些类似物对表皮生长因子受体（EGFR）的底物磷酸化没有影响，这种选择性是该类似物的最典型特征（1-12）。