3-(bis(4-chlorophenyl)methyl)pyridine | 5747-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(bis(4-chlorophenyl)methyl)pyridine
• 英文别名: bis(4-chlorophenyl)-3-pyridylmethane；3-bis(4-chlorophenyl)methylpyridine；α,α-Bis-(4-chlor-phenyl)-3-pyridyl-methan；3-[Bis-(4-chloro-phenyl)-methyl]-pyridine；3-[bis(4-chlorophenyl)methyl]pyridine
• CAS: 5747-90-0
• 化学式: C₁₈H₁₃Cl₂N
• 分子量: 314.214
• InChiKey: AWKPVXLLPWCTIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  194-196 °C(Press: 0.3 Torr)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(bis(4-chlorophenyl)methyl)pyridine 、 碘甲烷 在 potassium amide 作用下， 生成 3-<α-methyl-α-bis(4-chlorophenyl)methyl>pyridine
  参考文献：
  名称：

  雌激素合成酶抑制剂。2.比较体外芳香酶对被二芳基甲烷或二芳基甲醇基团取代的氮杂环的抑制活性。

  摘要：

  描述了多种杂环（4,4'-二氯二苯基）甲烷和-甲醇的制备和体外芳香酶抑制活性。通过将一系列咪唑和吡啶衍生的化合物与先前报道的类似嘧啶化合物进行比较，从而选择了两个带有二芳基的部分作为评估杂环的载体。还介绍了活性最高的化合物的结构模型。发现包含两个杂环部分的一系列相关化合物的活性与模型一致。评估的许多化合物（包括吡啶，咪唑，嘧啶，吡唑，三唑，噻唑和异噻唑类的代表）在低纳摩尔浓度下均具有EC50抑制芳香酶的能力。

  DOI：

  10.1021/jm00163a065
• 作为产物：
  描述：

  氯苯吡啶 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 反应 18.0h， 以17%的产率得到3-(bis(4-chlorophenyl)methyl)pyridine
  参考文献：
  名称：

  Analogues of Fenarimol Are Potent Inhibitors of Trypanosoma cruzi and Are Efficacious in a Murine Model of Chagas Disease

  摘要：

  We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC(50)s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.

  DOI：

  10.1021/jm2015809

文献信息

• 3-Pyridinecarboxaldehyde:  A Model System for Superelectrophilic Activation and the Observation of a Diprotonated Electrophile
  作者：Douglas A. Klumpp、Siufu Lau

  DOI：10.1021/jo9824908

  日期：1999.10.1

  3-Pyridinecarboxaldehyde (7) has been studied as a model system for superelectrophilic activation. When compound 7 is compared with benzaldehyde (3) in acid-catalyzed condensation reactions with arenes, 7 is more reactive than 3. Compound 7 reacts with chlorobenzene, o-dichlorobenzene, or nitrobenzene in CF3SO3H (triflic acid, TfOH) to give diaryl-3-pyridylmethanes, while 3 does not react with these deactivated arenes in TfOH. Moreover, 7 reacts with benzene in solutions as weakly acidic as H-o = -9, while 3 requires acidity in the range of H-o = -11.5 to -14 to reach a comparable level of electrophilic reactivity. Compound 7 was studied in acidic solution by C-13 NMR, and the diprotonated, dicationic species was observed at -60 degrees C in a solution of FSO3H-SbF5.
• US4757076A
  申请人：——

  公开号：US4757076A

  公开（公告）日：1988-07-12
• Estrogen synthetase inhibitors. 2. Comparison of the in vitro aromatase inhibitory activity for a variety of nitrogen heterocycles substituted with diarylmethane or diarylmethanol groups
  作者：C. David Jones、Mark A. Winter、Kenneth S. Hirsch、Nancy Stamm、Harold M. Taylor、Howard E. Holden、James D. Davenport、Eriks V. Krumkalns、Robert G. Suhr

  DOI：10.1021/jm00163a065

  日期：1990.1

  The preparation and in vitro aromatase inhibitory activity of a wide variety of heterocyclic (4,4'-dichlorodiphenyl)methanes and -methanols are described. The choice of the two diaryl-bearing moieties as a vehicle for the evaluation of the heterocycles was made by the comparison of series of imidazole and pyridine-derived compounds with similar pyrimidine compounds reported previously. A structural

  描述了多种杂环（4,4'-二氯二苯基）甲烷和-甲醇的制备和体外芳香酶抑制活性。通过将一系列咪唑和吡啶衍生的化合物与先前报道的类似嘧啶化合物进行比较，从而选择了两个带有二芳基的部分作为评估杂环的载体。还介绍了活性最高的化合物的结构模型。发现包含两个杂环部分的一系列相关化合物的活性与模型一致。评估的许多化合物（包括吡啶，咪唑，嘧啶，吡唑，三唑，噻唑和异噻唑类的代表）在低纳摩尔浓度下均具有EC50抑制芳香酶的能力。
• Analogues of Fenarimol Are Potent Inhibitors of Trypanosoma cruzi and Are Efficacious in a Murine Model of Chagas Disease
  作者：Martine Keenan、Michael J. Abbott、Paul W. Alexander、Tanya Armstrong、Wayne M. Best、Bradley Berven、Adriana Botero、Jason H. Chaplin、Susan A. Charman、Eric Chatelain、Thomas W. von Geldern、Maria Kerfoot、Andrea Khong、Tien Nguyen、Joshua D. McManus、Julia Morizzi、Eileen Ryan、Ivan Scandale、R. Andrew Thompson、Sen Z. Wang、Karen L. White

  DOI：10.1021/jm2015809

  日期：2012.5.10

  We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC(50)s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.