Phosphoric acid 4-[(S)-2-acetylamino-2-((R)-1-dipentylcarbamoyl-2-methylsulfanyl-ethylcarbamoyl)-ethyl]-phenyl ester di-tert-butyl ester | 205237-02-1

• 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: Phosphoric acid 4-[(S)-2-acetylamino-2-((R)-1-dipentylcarbamoyl-2-methylsulfanyl-ethylcarbamoyl)-ethyl]-phenyl ester di-tert-butyl ester
• 英文别名: [4-[(2S)-2-acetamido-3-[[(2R)-1-(dipentylamino)-3-methylsulfanyl-1-oxopropan-2-yl]amino]-3-oxopropyl]phenyl] ditert-butyl phosphate
• CAS: 205237-02-1
• 化学式: C₃₃H₅₈N₃O₇PS
• 分子量: 671.879
• InChiKey: BKCNJEKPUJMOBY-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  45
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Phosphoric acid 4-[(S)-2-acetylamino-2-((R)-1-dipentylcarbamoyl-2-methylsulfanyl-ethylcarbamoyl)-ethyl]-phenyl ester di-tert-butyl ester 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到Phosphoric acid mono-{4-[(S)-2-acetylamino-2-((R)-1-dipentylcarbamoyl-2-methylsulfanyl-ethylcarbamoyl)-ethyl]-phenyl} ester
  参考文献：
  名称：

  Potent Dipeptide Inhibitors of the pp60^c-src SH2 Domain

  摘要：

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.

  DOI：

  10.1021/jm970853a
• 作为产物：
  描述：

  tert-butyl N-[(2R)-1-(dipentylamino)-3-methylsulfanyl-1-oxopropan-2-yl]carbamate 在 盐酸 、 sodium hydride 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.5h， 生成 Phosphoric acid 4-[(S)-2-acetylamino-2-((R)-1-dipentylcarbamoyl-2-methylsulfanyl-ethylcarbamoyl)-ethyl]-phenyl ester di-tert-butyl ester
  参考文献：
  名称：

  Potent Dipeptide Inhibitors of the pp60^c-src SH2 Domain

  摘要：

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.

  DOI：

  10.1021/jm970853a

文献信息

• Potent Dipeptide Inhibitors of the pp60<i>^c</i><i>^-</i><i>^src</i> SH2 Domain
  作者：Gregory J. Pacofsky、Karen Lackey、Krystal J. Alligood、Judd Berman、Paul S. Charifson、Renae M. Crosby、George F. Dorsey,、Paul L. Feldman、Tona M. Gilmer、Conrad W. Hummel、Steven R. Jordan、Christopher Mohr、Lisa M. Shewchuk、Daniel D. Sternbach、Marc Rodriguez

  DOI：10.1021/jm970853a

  日期：1998.5.1

  The design, synthesis, and evaluation of dipeptide analogues as ligands for the pp60(c-src) SH2 domain are described. The critical binding interactions between Ac-Tyr-Glu-N(n-C5H11)(2) (2) and the protein are established and form the basis for our structure-based drug design efforts. The effects of changes in both the C-terminal (11-27) and N-terminal (51-69) portions of the dipeptide are explored. Analogues with reduced overall charge (92-95) are also investigated. We demonstrate the feasibility of pairing structurally diverse subunits in a modest dipeptide framework with the goal of increasing the druglike attributes without sacrificing binding affinity.