9-(5-azidopentyl)-9H-carbazole | 828941-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(5-azidopentyl)-9H-carbazole
• 英文别名: 9-(5-Azidopentyl)-9H-carbazole；9-(5-azidopentyl)carbazole
• CAS: 828941-34-0
• 化学式: C₁₇H₁₈N₄
• 分子量: 278.357
• InChiKey: ZFOPWFZQOARNAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  19.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(5-azidopentyl)-9H-carbazole 在 lithium hydroxide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (2S)-tert-butoxycarbonylamino-3-((1-((5-carbazol-9-yl)pentyl)-1H-[1,2,3]triazol-4-yl)methoxy)propionic acid
  参考文献：
  名称：

  Isoxazolyl-Serine-Based Agonists of Peroxisome Proliferator-Activated Receptor:  Design, Synthesis, and Effects on Cardiomyocyte Differentiation

  摘要：

  The peroxisome proliferator-activated receptors (PPARs) are important molecular targets for the development of drugs for the treatment of human metabolic diseases, inflammation, and cancer. They are known to be activated by a variety of structurally diverse compounds. Using a structure-based drug design approach, we designed and synthesized a series of novel isoxazolyl-serine-based PPAR ligands possessing moderate affinities. Some of the new PPAR ligands were able to stimulate cardiomyocyte differentiation from murine ES cells. Ligand 1a was the most active one tested at concentrations between 1.25 to 20 muM between days 2-6, coinciding with the period when mesodermal cells can be recruited to become cardiomyocytes. Notably, the known PPARalpha, gamma, and delta agonists tested, e.g., fenofibrate, rosiglitazone, and GW501516, were inactive in this assay.

  DOI：

  10.1021/ja046386l
• 作为产物：
  描述：

  9-(5-溴戊基)咔唑 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以94%的产率得到9-(5-azidopentyl)-9H-carbazole
  参考文献：
  名称：

  Isoxazolyl-Serine-Based Agonists of Peroxisome Proliferator-Activated Receptor:  Design, Synthesis, and Effects on Cardiomyocyte Differentiation

  摘要：

  The peroxisome proliferator-activated receptors (PPARs) are important molecular targets for the development of drugs for the treatment of human metabolic diseases, inflammation, and cancer. They are known to be activated by a variety of structurally diverse compounds. Using a structure-based drug design approach, we designed and synthesized a series of novel isoxazolyl-serine-based PPAR ligands possessing moderate affinities. Some of the new PPAR ligands were able to stimulate cardiomyocyte differentiation from murine ES cells. Ligand 1a was the most active one tested at concentrations between 1.25 to 20 muM between days 2-6, coinciding with the period when mesodermal cells can be recruited to become cardiomyocytes. Notably, the known PPARalpha, gamma, and delta agonists tested, e.g., fenofibrate, rosiglitazone, and GW501516, were inactive in this assay.

  DOI：

  10.1021/ja046386l

文献信息

• Isoxazolyl-Serine-Based Agonists of Peroxisome Proliferator-Activated Receptor:  Design, Synthesis, and Effects on Cardiomyocyte Differentiation
  作者：Zhi-Liang Wei、Pavel A. Petukhov、Fero Bizik、Joaquim Cabral Teixeira、Mark Mercola、Eugene A. Volpe、Robert I. Glazer、Timothy M. Willson、Alan P. Kozikowski

  DOI：10.1021/ja046386l

  日期：2004.12.1

  The peroxisome proliferator-activated receptors (PPARs) are important molecular targets for the development of drugs for the treatment of human metabolic diseases, inflammation, and cancer. They are known to be activated by a variety of structurally diverse compounds. Using a structure-based drug design approach, we designed and synthesized a series of novel isoxazolyl-serine-based PPAR ligands possessing moderate affinities. Some of the new PPAR ligands were able to stimulate cardiomyocyte differentiation from murine ES cells. Ligand 1a was the most active one tested at concentrations between 1.25 to 20 muM between days 2-6, coinciding with the period when mesodermal cells can be recruited to become cardiomyocytes. Notably, the known PPARalpha, gamma, and delta agonists tested, e.g., fenofibrate, rosiglitazone, and GW501516, were inactive in this assay.