3-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]-1-methyl-1H-7-azaindole | 1314083-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 3-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]-1-methyl-1H-7-azaindole
• 英文别名: 2-(4-Chlorophenyl)-4-(1-methylpyrrolo[2,3-b]pyridin-3-yl)-1,3-thiazole
• CAS: 1314083-08-3
• 化学式: C₁₇H₁₂ClN₃S
• 分子量: 325.821
• InChiKey: JYEHBUKQIFSWIM-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C(Solvent: Ethanol)
• 沸点：
  547.4±60.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-氮杂吲哚 在 aluminum (III) chloride 、 三(3,6-二氧杂庚基)胺 、 potassium tert-butylate 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 5.17h， 生成 3-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]-1-methyl-1H-7-azaindole
  参考文献：
  名称：

  Synthesis and Antitumor Activity of 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-indoles and 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-7-azaindoles

  摘要：

  AbstractGiven the potent antimicrobial, antiviral, and antitumor activities of many natural products, there is an increasing interest in the synthesis of new molecules based on natural compound scaffolds. Based on a 2,4‐bis(3′‐indolyl)imidazole skeleton, two new series of phenylthiazolylindoles and phenylthiazolyl‐7‐azaindoles were obtained by Hantzsch reaction between substituted phenylthioamides and the α‐bromoacetyl derivatives. Some azaindole derivatives, tested at the National Cancer Institute against a panel of ∼60 tumor cell lines derived from nine human cancer cell types, showed inhibitory effects against all cell lines investigated at micromolar to nanomolar concentrations. Two of them exhibited a high affinity for CDK1, with IC50 values of 0.41 and 0.85 μM. These promising results will set the foundation for future investigations into the development of anticancer therapies.

  DOI：

  10.1002/cmdc.201100078

文献信息

• Synthesis and Antitumor Activity of 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-indoles and 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-7-azaindoles
  作者：Patrizia Diana、Anna Carbone、Paola Barraja、Alessandra Montalbano、Barbara Parrino、Alessia Lopergolo、Marzia Pennati、Nadia Zaffaroni、Girolamo Cirrincione

  DOI：10.1002/cmdc.201100078

  日期：2011.7.4

  AbstractGiven the potent antimicrobial, antiviral, and antitumor activities of many natural products, there is an increasing interest in the synthesis of new molecules based on natural compound scaffolds. Based on a 2,4‐bis(3′‐indolyl)imidazole skeleton, two new series of phenylthiazolylindoles and phenylthiazolyl‐7‐azaindoles were obtained by Hantzsch reaction between substituted phenylthioamides and the α‐bromoacetyl derivatives. Some azaindole derivatives, tested at the National Cancer Institute against a panel of ∼60 tumor cell lines derived from nine human cancer cell types, showed inhibitory effects against all cell lines investigated at micromolar to nanomolar concentrations. Two of them exhibited a high affinity for CDK1, with IC50 values of 0.41 and 0.85 μM. These promising results will set the foundation for future investigations into the development of anticancer therapies.