Ethyl 5-<(S)-1-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>-1,2,4-oxadiazole-3-carboxylate | 164029-33-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 5-<(S)-1-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>-1,2,4-oxadiazole-3-carboxylate
• 英文别名: ethyl 5-[(S)-1-(tert-butyloxycarbonylamino)-2-phenylethyl]-1,2,4-oxadiazole-3-carboxylate；ethyl 5-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylethyl]-1,2,4-oxadiazole-3-carboxylate
• CAS: 164029-33-8
• 化学式: C₁₈H₂₃N₃O₅
• 分子量: 361.398
• InChiKey: JIGKCCSXYOZOTR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 5-<(S)-1-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>-1,2,4-oxadiazole-3-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 H-Tyr-D-Ala-{5-[(S)-1-amino-2-phenylethyl]-1,2,4-oxadiazol-3-ylcarbonyl}-Tyr-Pro-Ser-NH2
  参考文献：
  名称：

  Phe-Gly模拟物的设计，合成和评估：伪肽的杂环构件。

  摘要：

  含有1,3,4-恶二唑，1,2,4-恶二唑和1,2,4-三唑环系统的对映体杂环Boc保护的Phe-Gly二肽模拟物是伪肽合成中的结构单元。三个衍生物（1-3）具有直接键合到杂环上的羧酸官能团，并且三个衍生物（4-6）在杂环和酸官能团之间具有额外的亚甲基，以提高构象柔韧性。该模拟物用作生物活性肽dermorphin（Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH（2））和P物质（Arg-Pro-Lys-Pro-Gln的Phe-Gly替代品） -Gln-Phe-Phe-Gly-Leu-MetNH（2），SP）。使用Boc化学方法在MBHA树脂上使用固相方法进行假肽合成。通过测试dermorphin假肽的微阿片受体亲和力和SP假肽的NK（1）受体亲和力来进行生物学评估。结果表明，除3个模拟物外，其他所有模拟物均是dermorphin中Phe-Gly的极佳替代品，因为它们对微受体（IC（50）=

  DOI：

  10.1021/jm990197+
• 作为产物：
  描述：

  ethyl 2-oximinooxamate 、 Boc-Phe anhydride 以 吡啶 为溶剂， 反应 2.0h， 生成 Ethyl 5-<(R)-1-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>-1,2,4-oxadiazole-3-carboxylate 、 Ethyl 5-<(S)-1-<(tert-butyloxycarbonyl)amino>-2-phenylethyl>-1,2,4-oxadiazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics

  摘要：

  Three series of heterocyclic dipeptidomimetics have been synthesized. The compounds were designed as amino acid-glycine mimetics containing 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,4-triazole ring systems, useful as building blocks in the synthesis of modified peptides. The heterocyclic moieties were chosen according to their geometrical, electrostatical, and hydrogen bonding properties together with the synthetic accessibility. The syntheses started with Boc-protected L-amino acids (Ala, Gly, Asp, Phe, Ser, Arg, Cys, and Pro), and the reaction conditions were chosen to allow for the formation of products with high enantiopurity. The enantiomeric excess was determined by HPLC using chiral stationary phases.

  DOI：

  10.1021/jo00115a029

文献信息

• Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics
  作者：Susanna Borg、Genevieve Estenne-Bouhtou、Kristina Luthman、Ingeborg Csoeregh、Willy Hesselink、Uli Hacksell

  DOI：10.1021/jo00115a029

  日期：1995.5

  Three series of heterocyclic dipeptidomimetics have been synthesized. The compounds were designed as amino acid-glycine mimetics containing 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,4-triazole ring systems, useful as building blocks in the synthesis of modified peptides. The heterocyclic moieties were chosen according to their geometrical, electrostatical, and hydrogen bonding properties together with the synthetic accessibility. The syntheses started with Boc-protected L-amino acids (Ala, Gly, Asp, Phe, Ser, Arg, Cys, and Pro), and the reaction conditions were chosen to allow for the formation of products with high enantiopurity. The enantiomeric excess was determined by HPLC using chiral stationary phases.
• Design, Synthesis, and Evaluation of Phe-Gly Mimetics:  Heterocyclic Building Blocks for Pseudopeptides
  作者：Susanna Borg、Roeland C. Vollinga、Maryse Labarre、Kemal Payza、Lars Terenius、Kristina Luthman

  DOI：10.1021/jm990197+

  日期：1999.10.1

  ring systems have been synthesized as building blocks in the synthesis of pseudopeptides. Three derivatives (1-3) have the carboxylic acid function directly bound to the heterocyclic ring, and three derivatives (4-6) have an extra methylene group between the heterocyclic ring and the acid function to allow for an increased conformational flexibility. The mimetics were used as Phe-Gly replacements in

  含有1,3,4-恶二唑，1,2,4-恶二唑和1,2,4-三唑环系统的对映体杂环Boc保护的Phe-Gly二肽模拟物是伪肽合成中的结构单元。三个衍生物（1-3）具有直接键合到杂环上的羧酸官能团，并且三个衍生物（4-6）在杂环和酸官能团之间具有额外的亚甲基，以提高构象柔韧性。该模拟物用作生物活性肽dermorphin（Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH（2））和P物质（Arg-Pro-Lys-Pro-Gln的Phe-Gly替代品） -Gln-Phe-Phe-Gly-Leu-MetNH（2），SP）。使用Boc化学方法在MBHA树脂上使用固相方法进行假肽合成。通过测试dermorphin假肽的微阿片受体亲和力和SP假肽的NK（1）受体亲和力来进行生物学评估。结果表明，除3个模拟物外，其他所有模拟物均是dermorphin中Phe-Gly的极佳替代品，因为它们对微受体（IC（50）=