2-chloro-5-methyl-4,6-di(2'-thienyl)pyrimidine | 131022-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-chloro-5-methyl-4,6-di(2'-thienyl)pyrimidine
• 英文别名: 2-Chloro-5-methyl-4,6-bis(2-thienyl)pyrimidine；2-chloro-5-methyl-4,6-dithiophen-2-ylpyrimidine
• CAS: 131022-82-7
• 化学式: C₁₃H₉ClN₂S₂
• 分子量: 292.813
• InChiKey: ZRSJBFHSCFFLPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  437.4±40.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基丁醇 、 2-chloro-5-methyl-4,6-di(2'-thienyl)pyrimidine 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以50%的产率得到
  参考文献：
  名称：

  Chiral discrimination in binding of enantiomers of 2-(aminoalkoxy)-substituted 4-(2-thienyl)pyrimidines and 4,6-bis(2-thienyl)pyrimidines with duplex DNA

  摘要：

  Thienylpyrimidines substituted at position 2 of the pyrimidine with a chiral aminoalkoxy group were synthesized. Upon interaction with duplex DNA, the unfused heteroaromatic system of these compounds intercalates with DNA base pairs and the protonated side chain is located in the major groove. The S-enantiomers bind more strongly than their R-counterparts with enantiomeric discrimination, as measured by a ratio of binding constants K-S/K-R, ranging from 1.2 to 2.4. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.004
• 作为产物：
  描述：

  2-氯-5-甲基嘧啶 在 正丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 2-chloro-5-methyl-4,6-di(2'-thienyl)pyrimidine
  参考文献：
  名称：

  Strekowski, Lucjan; Harden, Donald B.; Grubb, William B., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1393 - 1400

  摘要：

  DOI：

文献信息

• Structure-Activity Relationship Studies of CNS Agents, Part 25: 4,6-Di(heteroaryl)-2-(N-methylpiperazino)pyrimidines as New, Potent 5-HT2A Receptor Ligands: A Verification of the Topographic Model
  作者：Maria J. Mokrosz、Lucjan Strekowski、Wei Xing Kozak、Beata Duszyńska、Andrzej J. Bojarski、Aleksandra Kłodzinska、Agnieszka Czarny、Marek T. Cegła、Anna Dereń-Wesołek、Ewa Chojnacka-Wójcik、Stefan Dove、Jerzy L. Mokrosz

  DOI：10.1002/ardp.19953280906

  日期：——

  A series of new 4,6‐di(heteroaryl)pyrimidines containing an N‐methylpiperazino group (6–13) or an ethylenediamine chain (15–20) in position 2 were synthesized and their 5‐HT1A and 5‐HT2A receptor affinities were determined. It was shown that the substituent effects on the 5‐HT2A affinity are additive and could be described quantitatively. In a behavioral model it was also demonstrated that 6–11 are

  合成了一系列新的 4,6-二（杂芳基）嘧啶，在 2 位含有一个 N-甲基哌嗪基（6-13）或乙二胺链（15-20），它们的 5-HT1A 和 5-HT2A 受体亲和力为决定。结果表明，对 5-HT2A 亲和力的取代效应是相加的，可以定量描述。在行为模型中，还证明 6-11 是 5-HT2A 受体拮抗剂。分子模拟结果表明，碱性氮原子和两个芳香中心之间的距离（d1 = 5.2-8.4 Å，d2 = 5.7-8.5 Å，d3 = 4.6-7.3 Å）定义了 5-HT2A 的分子形貌正在研究的受体拮抗剂。
• Chiral discrimination in binding of enantiomers of 2-(aminoalkoxy)-substituted 4-(2-thienyl)pyrimidines and 4,6-bis(2-thienyl)pyrimidines with duplex DNA
  作者：Lucjan Strekowski、Marek T. Cegla、Vidya Honkan、Henryk Buczak、W. Rucks Winkeljohn、Alfons L. Baumstark、W. David Wilson

  DOI：10.1016/j.bmcl.2005.04.004

  日期：2005.6

  Thienylpyrimidines substituted at position 2 of the pyrimidine with a chiral aminoalkoxy group were synthesized. Upon interaction with duplex DNA, the unfused heteroaromatic system of these compounds intercalates with DNA base pairs and the protonated side chain is located in the major groove. The S-enantiomers bind more strongly than their R-counterparts with enantiomeric discrimination, as measured by a ratio of binding constants K-S/K-R, ranging from 1.2 to 2.4. (c) 2005 Elsevier Ltd. All rights reserved.
• Strekowski, Lucjan; Harden, Donald B.; Grubb, William B., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1393 - 1400
  作者：Strekowski, Lucjan、Harden, Donald B.、Grubb, William B.、Patterson, Steven E.、Czarny, Agnieszka、et al.

  DOI：——

  日期：——