6-(4-bromophenyl)nicotinonitrile | 951658-02-9

• 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: 6-(4-bromophenyl)nicotinonitrile
• 英文别名: 2-(4'-bromophenyl)-5-pyridinecarbonitrile；6-(4-bromophenyl)pyridine-3-carbonitrile
• CAS: 951658-02-9
• 化学式: C₁₂H₇BrN₂
• 分子量: 259.105
• InChiKey: RCNNROHPLIXGEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-bromophenyl)nicotinonitrile 、 4-氰基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 以94%的产率得到phenyl[1,1']phenyl[4',2'']pyridinyl-4,5''-bis-carbonitrile
  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
• 作为产物：
  描述：

  4-溴苯硼酸 、 2-溴-5-氰基吡啶 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 以78%的产率得到6-(4-bromophenyl)nicotinonitrile
  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

• [EN] IMIDAZOLE BIARYL COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS<br/>[FR] COMPOSÉS IMIDAZOLE BIARYLE EN TANT QU'INHIBITEURS DE LA S-NITROSOGLUTATHION RÉDUCTASE
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2016046782A1

  公开（公告）日：2016-03-31

  The present disclosure is directed to compounds of formula (Ie) and pharmaceutically acceptable salts thereof, wherein A, B, R1, R2, m, n, X1, X2, X3 and X4 are as defined herein, which are active as inhibitors of S-Nitrosoglutathione reductase (GSNOR). These compounds prevent, inhibit, or suppress the action of GSNOR and are therefore useful in the treatment of GSNOR mediated diseases, disorders, syndromes or conditions such as, e.g., pulmonary hypertension, acute respiratory distress syndrome (ARDS), asthma, bronchospasm, cough, pneumonia, pulmonary fibrosis, interstitial lung diseases, cystic fibrosis and chronic obstructive pulmonary disease (COPD).

  本公开涉及式(Ie)的化合物及其药用盐，其中A、B、R1、R2、m、n、X1、X2、X3和X4如本文所定义，这些化合物作为S-硝基谷胱甘肽还原酶(GSNOR)的抑制剂具有活性。这些化合物可以防止、抑制或抑制GSNOR的作用，因此在治疗GSNOR介导的疾病、紊乱、综合征或病况方面具有用处，例如肺动脉高压、急性呼吸窘迫综合征(ARDS)、哮喘、支气管痉挛、咳嗽、肺炎、肺纤维化、间质性肺疾病、囊性纤维化和慢性阻塞性肺病(COPD)。
• 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。
• Teraryl components as antiparasitic agents
  申请人：The University of North Carolina at Chapel Hill

  公开号：US07964619B2

  公开（公告）日：2011-06-21

  Disclosed herein are novel dicationic teraryl compounds and their aza analogues, including compounds of Formula (IIe): wherein p and q are each 0 and each A, Y and Z is CR4. An exemplary compound of Formula (IIe) is: Methods for combating microbial infections, such as parasitic Leishmania species, with novel dicationic terphenyl compounds and their aza analogues are included. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues are disclosed along with methods for evaluation of the compounds as potential anti-protozoan agents.

  本文披露了新型二阳离子的三苯基化合物及其氮杂环类似物，包括公式（IIe）的化合物：其中p和q均为0，每个A，Y和Z均为CR4。公式（IIe）的一个示例化合物为：与新型二阳离子的三苯基化合物及其氮杂环类似物一起，还包括用于对抗微生物感染（如寄生虫利什曼体属）的方法。本文还披露了合成新型二阳离子的三苯基化合物及其氮杂环类似物的过程，以及评估这些化合物作为潜在抗原虫剂的方法。
• Substituted pyridines as antiparasitic AZA teraryl compounds
  申请人：The University of North Carolina at Chapel Hill

  公开号：US08188121B2

  公开（公告）日：2012-05-29

  Novel aza analogues of dicationic terphenyl compounds for use in combating microbial infections are described. The compounds include those of Formula (III): wherein one of A1, Y1, and Z1 is N; Ar1 is phenylene; and Ar3 is a nitrogen-containing aromatic group. An exemplary compound of Formula (III) is:

  本文描述了用于对抗微生物感染的二阳离子三苯基化合物的新型氮杂脲类似物。这些化合物包括公式（III）中的化合物：其中A1，Y1和Z1中的一个是N；Ar1是苯基；Ar3是含氮芳香族基团。公式（III）的示例化合物为：
• 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。