benzyl tert-butyl(6-nitropyridin-3-yl)propanedioate | 1603830-63-2

• 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: benzyl tert-butyl(6-nitropyridin-3-yl)propanedioate
• 英文别名: 3-O-benzyl 1-O-tert-butyl 2-(6-nitropyridin-3-yl)propanedioate
• CAS: 1603830-63-2
• 化学式: C₁₉H₂₀N₂O₆
• 分子量: 372.378
• InChiKey: PRXYDLFGLFIKGO-UHFFFAOYSA-N

物化性质

• 沸点：
  509.4±50.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  108.63
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl tert-butyl(6-nitropyridin-3-yl)propanedioate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以4.2 g的产率得到tert-butyl(6-aminopyridin-3-yl)acetate
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel polycyclic heteroarene ethers as PDE10A inhibitors: Part I

  摘要：

  We report analogue-based rational design and synthesis of two novel series of polycyclic heteroarenes, pyrrolo[3,2-b]quinolines and pyrido[2,3-b]indoles, tethered to a biaryl system by a methyl-, ethyl-or propyl ether as PDE10A inhibitors. A number of analogues were prepared with variable chain length and evaluated for their ability to block PDE10A enzyme using a radiometric assay. Detailed SAR analyses revealed that compounds with an ethyl ether linker are superior in potency compared to compounds with methyl or propyl ether linkers. These compounds, in general, showed poor metabolic stability in rat and human liver microsomes. The metabolic profile of one of the potent compounds was studied in detail to identify metabolic liabilities of these compounds. Structural modifications were carried out that resulted in improved metabolic stability without significant loss of potency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.054
• 作为产物：
  描述：

  5-溴-2-硝基吡啶 、 丙二酸叔丁酯苯甲酯 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以6.5 g的产率得到benzyl tert-butyl(6-nitropyridin-3-yl)propanedioate
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel polycyclic heteroarene ethers as PDE10A inhibitors: Part I

  摘要：

  We report analogue-based rational design and synthesis of two novel series of polycyclic heteroarenes, pyrrolo[3,2-b]quinolines and pyrido[2,3-b]indoles, tethered to a biaryl system by a methyl-, ethyl-or propyl ether as PDE10A inhibitors. A number of analogues were prepared with variable chain length and evaluated for their ability to block PDE10A enzyme using a radiometric assay. Detailed SAR analyses revealed that compounds with an ethyl ether linker are superior in potency compared to compounds with methyl or propyl ether linkers. These compounds, in general, showed poor metabolic stability in rat and human liver microsomes. The metabolic profile of one of the potent compounds was studied in detail to identify metabolic liabilities of these compounds. Structural modifications were carried out that resulted in improved metabolic stability without significant loss of potency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.054

文献信息

• [EN] PROTEIN TYROSINE PHOSPHATASE DEGRADERS AND METHODS OF USE THEREOF<br/>[FR] AGENTS DE DÉGRADATION DE PROTÉINE TYROSINE PHOSPHATASE ET LEURS MÉTHODES D'UTILISATION
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2021127586A1

  公开（公告）日：2021-06-24

  Provided herein are compounds, compositions, and methods useful for degrading protein tyrosine phosphatase, e.g., protein tyrosine phosphatase non-receptor type 2 (PTPN2) and/or protein tyrosine phosphatase non-receptor type 1 (PTPN1), and for treating related diseases favorably responsive to PTPN1 or PTPN2 inhibitor treatment, e.g., a cancer 5 or a metabolic disease.

  本文提供了一些有用于降解蛋白酪氨酸磷酸酶的化合物、组合物和方法，例如蛋白酪氨酸磷酸酶非受体型2（PTPN2）和/或蛋白酪氨酸磷酸酶非受体型1（PTPN1），以及用于治疗对PTPN1或PTPN2抑制剂治疗有良好反应的相关疾病，例如癌症或代谢性疾病。
• PROTEIN TYROSINE PHOSPHATASE DEGRADERS AND METHODS OF USE THEREOF
  申请人：Calico Life Sciences LLC

  公开号：EP4077319A1

  公开（公告）日：2022-10-26