4-((pyridin-3-ylmethyl)thio)-1H-pyrazolo[3,4-d]pyrimidine | 106651-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 4-((pyridin-3-ylmethyl)thio)-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 4-(3-pyridylmethylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine；4-(pyridin-3-ylmethylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine
• CAS: 106651-65-4
• 化学式: C₁₁H₉N₅S
• 分子量: 243.292
• InChiKey: YJQNUFCTHNSBRA-UHFFFAOYSA-N

物化性质

• 沸点：
  412.6±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  92.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((pyridin-3-ylmethyl)thio)-1H-pyrazolo[3,4-d]pyrimidine 、 3-溴丙烯 在 base 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1-Allyl-4-(3-pyridylmethylsulfanyl)pyrazolo[3,4-d]pyrimidine 、
  参考文献：
  名称：

  New thiopyrazolo[3,4-d]pyrimidine derivatives as anti-mycobacterial agents

  摘要：

  The multiple parallel synthesis of a series of N,S-bis-alkylated thiopyrazolo[3,4-d]pyrimidines, based on sequential S- then N-alkylation, is reported. These compounds showed significant anti-mycobacterial activity (MICs down to < 2 mu/ml) and their potential as significant drug-like leads is substantiated through cytotoxicity evaluation and in silico profiling. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.066
• 作为产物：
  描述：

  3-吡啶甲烷硫醇(6ci,7ci,8ci,9ci) 、 4-氯-1H-吡唑并[3,4-d]嘧啶 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以37%的产率得到4-((pyridin-3-ylmethyl)thio)-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  未保护的吲唑对开环异构化具有弹性：以强碱存在下的催化C-S偶联为例

  摘要：

  吲唑是药物化学中的一种特殊支架。然而，在强碱的存在下，N-保护的吲唑易于发生不希望的开环反应以释放邻氨基苯甲腈。通过使用带有NH键的未保护的吲唑，由于杂环被原位去质子化，因此可以避免异构化。我们在本文中报道了在双（三甲基甲硅烷基）酰胺锂存在下，溴吲唑与具有不同电子性质的硫醇的官能团耐受性和稳健的C–S偶联。

  DOI：

  10.1021/acs.joc.7b02712

文献信息

• 2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives: New bronchosecretolytic agents
  作者：Helmut Schickaneder、Heidrun Engler、Istvan Szelenyi

  DOI：10.1021/jm00386a018

  日期：1987.3

  2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives (1a-n) promote the excretion of phenol red into the mouse trachea, indicating an increased tracheobronchial secretion. Furthermore, 2-[(3-pyridinylmethyl)thio]pyrimidine (1a) (tasuldine) produces greater excretion of phenol red into the mouse trachea after systemic administration than the known bronchosecretolytic ambroxol. Compound 1a also reduces the viscosity of canine bronchial mucus. Compound 1a has been selected for clinical investigations.
• New thiopyrazolo[3,4-d]pyrimidine derivatives as anti-mycobacterial agents
  作者：Lluis Ballell、Robert A. Field、Gavin A.C. Chung、Robert J. Young

  DOI：10.1016/j.bmcl.2006.12.066

  日期：2007.3

  The multiple parallel synthesis of a series of N,S-bis-alkylated thiopyrazolo[3,4-d]pyrimidines, based on sequential S- then N-alkylation, is reported. These compounds showed significant anti-mycobacterial activity (MICs down to < 2 mu/ml) and their potential as significant drug-like leads is substantiated through cytotoxicity evaluation and in silico profiling. (c) 2007 Elsevier Ltd. All rights reserved.
• Unprotected Indazoles Are Resilient to Ring-Opening Isomerization: A Case Study on Catalytic C–S Couplings in the Presence of Strong Base
  作者：Jacob M. Ganley、Charles S. Yeung

  DOI：10.1021/acs.joc.7b02712

  日期：2017.12.15

  Indazoles represent a privileged scaffold in medicinal chemistry. In the presence of strong base, however, N-protected indazoles are prone to an undesirable ring-opening reaction to liberate o-aminobenzonitriles. By employing unprotected indazoles with a free N–H bond, isomerization is averted because the heterocycle is deprotonated in situ. We herein report functional group-tolerant and robust C–S

  吲唑是药物化学中的一种特殊支架。然而，在强碱的存在下，N-保护的吲唑易于发生不希望的开环反应以释放邻氨基苯甲腈。通过使用带有NH键的未保护的吲唑，由于杂环被原位去质子化，因此可以避免异构化。我们在本文中报道了在双（三甲基甲硅烷基）酰胺锂存在下，溴吲唑与具有不同电子性质的硫醇的官能团耐受性和稳健的C–S偶联。