(5S)-N,2-dimethyl-5-(prop-1-en-2-yl)cyclohexan-1-amine | 1259403-91-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5S)-N,2-dimethyl-5-(prop-1-en-2-yl)cyclohexan-1-amine
• 英文别名: (5S)-N,2-dimethyl-5-prop-1-en-2-ylcyclohexan-1-amine
• CAS: 1259403-91-2
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: YNRLAXGIZSJAKU-YVNMAJEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S)-N,2-dimethyl-5-(prop-1-en-2-yl)cyclohexan-1-amine 、 4-氯吡咯并嘧啶 在 三乙胺 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以10.4 mg的产率得到N-methyl-N-((5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Discovery of CP-690,550: A Potent and Selective Janus Kinase (JAK) Inhibitor for the Treatment of Autoimmune Diseases and Organ Transplant Rejection

  摘要：

  There is a critical need for safer and more convenient treatments for organ transplant rejection and autoimmune disorders such as rheumatoid arthritis. Janus tyrosine kinases (JAK1, JAK3) are expressed in lymphoid cells and are involved in the signaling of multiple cytokines important for various T cell functions. Blockade of the JAK1/JAK3-STAT pathway with a small molecule was anticipated to provide therapeutic immunosuppression/immunomodulation. The Pfizer compound library was screened against the catalytic domain of JAK3 resulting in the identification of a pyrrolopyrimidine-based series of inhibitors represented by CP-352,664 (2a). Synthetic analogues of 2a were screened against the JAK enzymes and evaluated in an IL-2 induced T cell blast proliferation assay. Select compounds were evaluated in rodent efficacy models of allograft rejection and destructive inflammatory arthritis. Optimization within this chemical series led to identification of CP-690,550 1, a potential first-in-class JAK inhibitor for treatment of autoimmune diseases and organ transplant rejection.

  DOI：

  10.1021/jm1004286
• 作为产物：
  描述：

  dihydrocarvone 、 甲胺 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (5S)-N,2-dimethyl-5-(prop-1-en-2-yl)cyclohexan-1-amine
  参考文献：
  名称：

  Discovery of CP-690,550: A Potent and Selective Janus Kinase (JAK) Inhibitor for the Treatment of Autoimmune Diseases and Organ Transplant Rejection

  摘要：

  There is a critical need for safer and more convenient treatments for organ transplant rejection and autoimmune disorders such as rheumatoid arthritis. Janus tyrosine kinases (JAK1, JAK3) are expressed in lymphoid cells and are involved in the signaling of multiple cytokines important for various T cell functions. Blockade of the JAK1/JAK3-STAT pathway with a small molecule was anticipated to provide therapeutic immunosuppression/immunomodulation. The Pfizer compound library was screened against the catalytic domain of JAK3 resulting in the identification of a pyrrolopyrimidine-based series of inhibitors represented by CP-352,664 (2a). Synthetic analogues of 2a were screened against the JAK enzymes and evaluated in an IL-2 induced T cell blast proliferation assay. Select compounds were evaluated in rodent efficacy models of allograft rejection and destructive inflammatory arthritis. Optimization within this chemical series led to identification of CP-690,550 1, a potential first-in-class JAK inhibitor for treatment of autoimmune diseases and organ transplant rejection.

  DOI：

  10.1021/jm1004286

文献信息

• Discovery of CP-690,550: A Potent and Selective Janus Kinase (JAK) Inhibitor for the Treatment of Autoimmune Diseases and Organ Transplant Rejection
  作者：Mark E. Flanagan、Todd A. Blumenkopf、William H. Brissette、Matthew F. Brown、Jeffrey M. Casavant、Chang Shang-Poa、Jonathan L. Doty、Eileen A. Elliott、Michael B. Fisher、Michael Hines、Craig Kent、Elizabeth M. Kudlacz、Brett M. Lillie、Kelly S. Magnuson、Sandra P. McCurdy、Michael J. Munchhof、Bret D. Perry、Perry S. Sawyer、Timothy J. Strelevitz、Chakrapani Subramanyam、Jianmin Sun、David A. Whipple、Paul S. Changelian

  DOI：10.1021/jm1004286

  日期：2010.12.23

  There is a critical need for safer and more convenient treatments for organ transplant rejection and autoimmune disorders such as rheumatoid arthritis. Janus tyrosine kinases (JAK1, JAK3) are expressed in lymphoid cells and are involved in the signaling of multiple cytokines important for various T cell functions. Blockade of the JAK1/JAK3-STAT pathway with a small molecule was anticipated to provide therapeutic immunosuppression/immunomodulation. The Pfizer compound library was screened against the catalytic domain of JAK3 resulting in the identification of a pyrrolopyrimidine-based series of inhibitors represented by CP-352,664 (2a). Synthetic analogues of 2a were screened against the JAK enzymes and evaluated in an IL-2 induced T cell blast proliferation assay. Select compounds were evaluated in rodent efficacy models of allograft rejection and destructive inflammatory arthritis. Optimization within this chemical series led to identification of CP-690,550 1, a potential first-in-class JAK inhibitor for treatment of autoimmune diseases and organ transplant rejection.