N-α,γ-di-tert.-butyloxycarbonyl-L-diaminobutyric acid | 1025949-95-4

• 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: N-α,γ-di-tert.-butyloxycarbonyl-L-diaminobutyric acid
• 英文别名: Boc-Dab(Boc)-piperidide；tert-butyl N-[(2S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxo-1-piperidin-1-ylbutan-2-yl]carbamate
• CAS: 1025949-95-4
• 化学式: C₁₉H₃₅N₃O₅
• 分子量: 385.504
• InChiKey: HWUKWUQYZRYULI-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-α,γ-di-tert.-butyloxycarbonyl-L-diaminobutyric acid 在 劳森试剂 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 1-[(S)-2,4-diaminobutanoyl]thioxopiperidine bistrifluoroacetate
  参考文献：
  名称：

  Design, Synthesis, and SAR of Potent and Selective Dipeptide-Derived Inhibitors for Dipeptidyl Peptidases

  摘要：

  In this paper we report the systematic search for new, potent, and selective DPP II inhibitors. A study of the structure-activity relationship was conducted starting from aminoacyl pyrrolidides as lead compounds. Rational exploration of the P-1 and P-2 building blocks led to the discovery of some very potent DPP II inhibitors which can be characterized by their high selectivity for DPP II with regard to DPP IV. Dab-Pip and Dab-Pip-2-CN were selected as the most promising inhibitors (IC50 nM range) and will enable us to study the physiological role of DPP II and to differentiate between DPP 11 and DPP IV in biological systems.

  DOI：

  10.1021/jm0308803
• 作为产物：
  描述：

  哌啶 、 (2S)-2,4-二({[(2-甲基-2-丙基)氧基]羰基}氨基)丁酸 在 PS-carbodiimide 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 N-α,γ-di-tert.-butyloxycarbonyl-L-diaminobutyric acid
  参考文献：
  名称：

  Design, Synthesis, and SAR of Potent and Selective Dipeptide-Derived Inhibitors for Dipeptidyl Peptidases

  摘要：

  In this paper we report the systematic search for new, potent, and selective DPP II inhibitors. A study of the structure-activity relationship was conducted starting from aminoacyl pyrrolidides as lead compounds. Rational exploration of the P-1 and P-2 building blocks led to the discovery of some very potent DPP II inhibitors which can be characterized by their high selectivity for DPP II with regard to DPP IV. Dab-Pip and Dab-Pip-2-CN were selected as the most promising inhibitors (IC50 nM range) and will enable us to study the physiological role of DPP II and to differentiate between DPP 11 and DPP IV in biological systems.

  DOI：

  10.1021/jm0308803

文献信息

• [EN] DIPEPTIDYL PEPTIDASE INHIBITORS<br/>[FR] INHIBITEURS DE DIPEPTIDYLE PEPTIDASE
  申请人：AIC

  公开号：WO2004076433A1

  公开（公告）日：2004-09-10

  The present invention relates to novel inhibitors of serine type peptidases in general and of serine type dipeptidyl peptidases in particular. The present invention further relates to the use of the dipeptidyl peptidase inhibitors for selective inhibition of dipeptidyl peptidases. The present invention also relates to pharmaceutical compositions comprising these novel dipeptidyl peptidase inhibitors. The present invention further relates to the use of the novel inhibitors in therapy, diagnosis and research.

  本发明涉及一般性的新型丝氨酸型肽酶抑制剂，特别是丝氨酸型二肽基肽酶的抑制剂。本发明还涉及利用二肽基肽酶抑制剂对二肽基肽酶进行选择性抑制。本发明还涉及包含这些新型二肽基肽酶抑制剂的药物组合物。本发明还涉及在治疗、诊断和研究中使用这些新型抑制剂。
• Design, Synthesis, and SAR of Potent and Selective Dipeptide-Derived Inhibitors for Dipeptidyl Peptidases
  作者：Kristel Senten、Pieter Van der Veken、Ingrid De Meester、Anne-Marie Lambeir、Simon Scharpé、Achiel Haemers、Koen Augustyns

  DOI：10.1021/jm0308803

  日期：2003.11.1

  In this paper we report the systematic search for new, potent, and selective DPP II inhibitors. A study of the structure-activity relationship was conducted starting from aminoacyl pyrrolidides as lead compounds. Rational exploration of the P-1 and P-2 building blocks led to the discovery of some very potent DPP II inhibitors which can be characterized by their high selectivity for DPP II with regard to DPP IV. Dab-Pip and Dab-Pip-2-CN were selected as the most promising inhibitors (IC50 nM range) and will enable us to study the physiological role of DPP II and to differentiate between DPP 11 and DPP IV in biological systems.