5-(2'-chloropyridin-5'-yl)-2-pyridinecarbonitrile | 951658-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(2'-chloropyridin-5'-yl)-2-pyridinecarbonitrile
• 英文别名: 5-(6-Chloropyridin-3-yl)pyridine-2-carbonitrile
• CAS: 951658-09-6
• 化学式: C₁₁H₆ClN₃
• 分子量: 215.642
• InChiKey: KAEBHLCDAXBSTK-UHFFFAOYSA-N

物化性质

• 熔点：
  220-224 °C
• 沸点：
  418.8±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2'-chloropyridin-5'-yl)-2-pyridinecarbonitrile 、 4-氰基苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 甲苯 为溶剂， 生成 phenyl[1,2']pyridinyl[5',5'']pyridinyl-4,2''-bis-carbonitrile
  参考文献：
  名称：

  Azaterphenyl diamidines as antileishmanial agents

  摘要：

  Eighteen diamidino azaterphenyls and analogues were evaluated as anti-leishmanials; nine of the compounds gave IC50 values less than 1 mu M, five exhibited values less than 0.40 mu M, and two gave values less than 0.10 mu M in a Leishmania donovani axenic amastigote assay. The activity of the diamidines strongly depends on the ring N-atom location relative to the amidine groups and correlates with DNA affinity. Transmission electron microscopy studies showed a dramatic dilation of the mitochondrion and evidence of disintegration of the kinetoplast of the amastigotes. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.091
• 作为产物：
  描述：

  5-溴-2-氰基吡啶 、 2-氯-5-吡啶硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 以98%的产率得到5-(2'-chloropyridin-5'-yl)-2-pyridinecarbonitrile
  参考文献：
  名称：

  Synthesis and activity of azaterphenyl diamidines against Trypanosoma brucei rhodesiense and Plasmodium falciparum

  摘要：

  A series of azaterphenyl diamidines has been synthesized and evaluated for in vitro antiprotozoal activity against both Trypanosoma brucei rhodesiense (T. b .r.) and Plasmodium falciparum (P. f.) and in vivo efficacy in the STIB900 acute mouse model for T. b. r. Six of the 13 compounds showed IC50 values less than 7 nM against T. b. r. Twelve of those exhibited IC50 values less than 6 nM against P. f. and six of those showed IC50 values <= 60.6 nM, which are more than 25-fold as potent as furamidine. Moreover, two of them showed more than 40-fold selectivity for P. f. versus T. b. r. Three compounds 15b, 19d and 19e exhibited in vivo efficacy against T. b. r. much superior to furamidine, and equivalent to or better than azafuramidine. The antiparasitic activity of these diamidines depends on the ring nitrogen atom(s) location relative to the amidine groups and generally correlates with DNA binding affinity. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.07.080

文献信息

• Linear dicationic terphenyls and their aza analogues as antiparasitic agents
  申请人：Tidwell R. Richard

  公开号：US20070232621A1

  公开（公告）日：2007-10-04

  Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues.

  小说二价离子三苯基化合物及其氮杂环类似物。使用小说二价离子三苯基化合物及其氮杂环类似物对微生物感染进行作战的方法。合成小说二价离子三苯基化合物及其氮杂环类似物的过程。
• NOVEL TERARYL COMPOUNDS AS ANTIPARASITIC AGENTS
  申请人：Tidwell Richard R.

  公开号：US20110257199A1

  公开（公告）日：2011-10-20

  Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues.

  小说二元离子三苯基化合物及其氮杂环类似物。使用小说二元离子三苯基化合物及其氮杂环类似物对抗微生物感染的方法。合成小说二元离子三苯基化合物及其氮杂环类似物的过程。
• Azaterphenyl diamidines as antileishmanial agents
  作者：Laixing Hu、Reem K. Arafa、Mohamed A. Ismail、Tanja Wenzler、Reto Brun、Manoj Munde、W. David Wilson、Sandra Nzimiro、Serene Samyesudhas、Karl A. Werbovetz、David W. Boykin

  DOI：10.1016/j.bmcl.2007.10.091

  日期：2008.1

  Eighteen diamidino azaterphenyls and analogues were evaluated as anti-leishmanials; nine of the compounds gave IC50 values less than 1 mu M, five exhibited values less than 0.40 mu M, and two gave values less than 0.10 mu M in a Leishmania donovani axenic amastigote assay. The activity of the diamidines strongly depends on the ring N-atom location relative to the amidine groups and correlates with DNA affinity. Transmission electron microscopy studies showed a dramatic dilation of the mitochondrion and evidence of disintegration of the kinetoplast of the amastigotes. (C) 2007 Elsevier Ltd. All rights reserved.
• US7964619B2
  申请人：——

  公开号：US7964619B2

  公开（公告）日：2011-06-21
• US8188121B2
  申请人：——

  公开号：US8188121B2

  公开（公告）日：2012-05-29