2,4,4'-trichloro-benzhydryl chloride | 856192-70-6

• 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: 2,4,4'-trichloro-benzhydryl chloride
• 英文别名: 2,4,4'-Trichlor-benzhydrylchlorid；2,4-Dichloro-1-[chloro-(4-chlorophenyl)methyl]benzene
• CAS: 856192-70-6
• 化学式: C₁₃H₈Cl₄
• 分子量: 306.019
• InChiKey: ABEUKHZPGPSJDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  咪唑 、 2,4,4'-trichloro-benzhydryl chloride 以 1,4-二氧六环 为溶剂， 生成 2,4,4'-trichlorobenzhydryl-1H-imidazole
  参考文献：
  名称：

  联苯苄唑衍生物的合成、抗菌和抗真菌活性

  摘要：

  合成了两个系列的氯化二苯甲基咪唑和三唑衍生物，并针对强致病菌的代表性菌株（金黄色葡萄球菌 CIP 4.83、伊氏埃希氏菌 CIP 5855、铜绿假单胞菌 CIP 82118、大肠杆菌CIP 和真菌 IP 53126）进行了体外测试白色念珠菌 IP 48.72、克柔念珠菌 IP 208.52、红色毛癣菌 IP 1657.86)。这些化合物中的大多数没有任何抗菌活性，但其中一些抑制红色毛癣菌的 MIC 值在 0.125 至 32 µg/mL 范围内，类似于或优于联苯苄唑和克霉唑，用作标准对照。在这些化合物中用三唑部分取代咪唑环导致抗真菌活性较低的衍生物。

  DOI：

  10.1002/ardp.201000304
• 作为产物：
  描述：

  (4-chlorophenyl)(2,4-dichlorophenyl)methanol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 2,4,4'-trichloro-benzhydryl chloride
  参考文献：
  名称：

  Design, synthesis and biological evaluation of piperazine analogues as CB1 cannabinoid receptor ligands

  摘要：

  After the CB1 receptor antagonist SR141716 (rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. Several series of urea, carbamate, amide, sulfonamide and oxalamide derivatives based on 1-benzhydrylpiperazine scaffold were synthesized and tested for CB1 receptor binding affinity. The SAR studies to optimize the CB1 binding affinity led to the potent urea derivatives. After the additional SAR studies to optimize the substituents of diphenyl rings, the combination of 2-chlorophenyl and 4-chlorophenyl turned out to be the most potent scaffold. The CB2 binding affinity assay as well as functional assay was also conducted on these compounds. Herein we wish to introduce several novel CB1 antagonists with IC50 values less than 100 nM for the CB1 receptor binding. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.023

文献信息

• The Effect of Substitution on the Solvolysis Rates of Benzhydryl Chlorides¹
  作者：Siegfried Altscher、Richard Baltzly、Samuel W. Blackman

  DOI：10.1021/ja01134a054

  日期：1952.7
• Synthesis, Antibacterial and Antifungal Activities of Bifonazole Derivatives
  作者：Salomé El Hage、Barbora Lajoie、Catherine Feuillolay、Christine Roques、Geneviève Baziard

  DOI：10.1002/ardp.201000304

  日期：2011.6

  compounds were devoid of any antimicrobial activity, but several of them inhibited T. rubrum with MIC values in the range of 0.125 to 32 µg/mL, similar or superior to those of bifonazole and clotrimazole, used as standard controls. The replacement of the imidazole ring with a triazole moiety in these compounds led to derivatives with less antifungal activity. A preliminary SAR was undertaken on the effect

  合成了两个系列的氯化二苯甲基咪唑和三唑衍生物，并针对强致病菌的代表性菌株（金黄色葡萄球菌 CIP 4.83、伊氏埃希氏菌 CIP 5855、铜绿假单胞菌 CIP 82118、大肠杆菌CIP 和真菌 IP 53126）进行了体外测试白色念珠菌 IP 48.72、克柔念珠菌 IP 208.52、红色毛癣菌 IP 1657.86)。这些化合物中的大多数没有任何抗菌活性，但其中一些抑制红色毛癣菌的 MIC 值在 0.125 至 32 µg/mL 范围内，类似于或优于联苯苄唑和克霉唑，用作标准对照。在这些化合物中用三唑部分取代咪唑环导致抗真菌活性较低的衍生物。
• Design, synthesis and biological evaluation of piperazine analogues as CB1 cannabinoid receptor ligands
  作者：Kwang-Seop Song、Sung-Han Lee、Hyun Ji Chun、Jong Yup Kim、Myung Eun Jung、Kwangwoo Ahn、Soo-Un Kim、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmc.2008.01.023

  日期：2008.4.1

  After the CB1 receptor antagonist SR141716 (rimonabant) was previously reported to modulate food intake, CB1 antagonism has been considered as a new therapeutic target for the treatment of obesity. Several series of urea, carbamate, amide, sulfonamide and oxalamide derivatives based on 1-benzhydrylpiperazine scaffold were synthesized and tested for CB1 receptor binding affinity. The SAR studies to optimize the CB1 binding affinity led to the potent urea derivatives. After the additional SAR studies to optimize the substituents of diphenyl rings, the combination of 2-chlorophenyl and 4-chlorophenyl turned out to be the most potent scaffold. The CB2 binding affinity assay as well as functional assay was also conducted on these compounds. Herein we wish to introduce several novel CB1 antagonists with IC50 values less than 100 nM for the CB1 receptor binding. (C) 2008 Elsevier Ltd. All rights reserved.