3-(4-chlorobutoxy)benzamide | 1384187-39-6

• 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: 3-(4-chlorobutoxy)benzamide
• CAS: 1384187-39-6
• 化学式: C₁₁H₁₄ClNO₂
• 分子量: 227.691
• InChiKey: MJSBGVPYHDTKEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-chlorobutoxy)benzamide 、 3-(1-哌嗪基)苯并异噻唑盐酸盐 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以28%的产率得到3-(4-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)butoxy)benzamide
  参考文献：
  名称：

  新型苯甲酰胺衍生物作为潜在抗精神病药的构效关系研究的继续

  摘要：

  合成了一系列具有强效多巴胺 D2、5-羟色胺 5-HT1A 和 5-HT2A 受体特性的苯甲酰胺衍生物，并将其评估为潜在的抗精神病药。其中，5-(4-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)butoxy)-N-cyclopropyl-2-fluorobenzamide (4k) 具有最好的药理学特征。它不仅对 D2、5-HT1A 和 5-HT2A 受体表现出强效和平衡的活性，而且对 5-HT2C、H1 和 M3 受体也具有低至中度的活性，这表明其诱导体重的倾向较低增益或糖尿病。在动物模型中，化合物 4k 减少了苯环利定诱导的多动症，具有高阈值的僵住症或肌肉松弛诱导。基于其在精神分裂症临床前模型中的强大体外效力和体内功效，

  DOI：

  10.1002/ardp.201800306
• 作为产物：
  描述：

  Methyl 3-(4-chlorobutoxy)benzoate 在 ammonium hydroxide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 3-(4-chlorobutoxy)benzamide
  参考文献：
  名称：

  新型苯甲酰胺衍生物作为潜在抗精神病药的构效关系研究的继续

  摘要：

  合成了一系列具有强效多巴胺 D2、5-羟色胺 5-HT1A 和 5-HT2A 受体特性的苯甲酰胺衍生物，并将其评估为潜在的抗精神病药。其中，5-(4-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)butoxy)-N-cyclopropyl-2-fluorobenzamide (4k) 具有最好的药理学特征。它不仅对 D2、5-HT1A 和 5-HT2A 受体表现出强效和平衡的活性，而且对 5-HT2C、H1 和 M3 受体也具有低至中度的活性，这表明其诱导体重的倾向较低增益或糖尿病。在动物模型中，化合物 4k 减少了苯环利定诱导的多动症，具有高阈值的僵住症或肌肉松弛诱导。基于其在精神分裂症临床前模型中的强大体外效力和体内功效，

  DOI：

  10.1002/ardp.201800306

文献信息

• Synthesis and on-target antibacterial activity of novel 3-elongated arylalkoxybenzamide derivatives as inhibitors of the bacterial cell division protein FtsZ
  作者：Siti Ma、Chao Cong、Xiaohui Meng、Shasha Cao、Hongkun Yang、Yuanyuan Guo、Xueyi Lu、Shutao Ma

  DOI：10.1016/j.bmcl.2013.05.056

  日期：2013.7

  Novel 3-elongated arylalkoxybenzamide derivatives were designed, synthesized and evaluated for their cell division inhibitory activity and antibacterial activity. Among them, the subseries of 3-alkyloxybenzamide derivatives exhibited greatly improved on-target activity against Bacillus subtilis and Staphylococcus aureus, and remarkably increased antibacterial activity against B. subtilis ATCC9372, penicillin-susceptible S. aureus ATCC25923, methicillin-resistant S. aureus ATCC29213 (MRSA) and penicillin-resistant S. aureus PR compared with 3-methoxybenzamide. In contrast, the subseries of 3-phenoxyaklyloxybenzamide, 3-heteroarylalkyloxybenzamide and 3-heteroarylthioalkyloxybenzamide derivatives only showed a significant improvement in on-target activity and antibacterial activity against B. subtilis ATCC9372. (C) 2013 Elsevier Ltd. All rights reserved.
• Effects of chronic mild stress on rats selectively bred for behavior related to bipolar disorder and depression
  作者：Ryan Murray、Katherine A. Boss-Williams、Jay M. Weiss

  DOI：10.1016/j.physbeh.2013.05.042

  日期：2013.7

  To test the possibility that chronic mild stress (CMS) might be unreliable in producing its often-intended outcome (i.e., decreased preference for sucrose, hypothesized to represent depression-relevant anhedonia) because it is typically applied to "normal" rats, a CMS procedure was applied to rats that may possess genetic susceptibility to affective disorders, having had been selectively-bred to show behavior indicative of such disorders. These rat lines were: Hyperactive (HYPER) rats, which show characteristics of bipolar disorder, Swim-test Susceptible (SUS) and Swim-test Resistant (RES) rats, being susceptible or resistant to effects of stress in the swim test, Swim High-active (SwHi) and Swim Low-active (SwLo) rats, which innately show high or low activity in the swim test These selectively-bred lines were compared to normal, non-selectively bred (NS) rats. During CMS, HYPER rats, both females and males, as well as RES and SwHi rats, showed reduced consumption of a palatable 2% sucrose solution, and reduced preference for sucrose (vs. water) in comparison to non-stressed rats (no CMS) of the same lines. In contrast, CMS produced no decrease in sucrose consumption or in preference for sucrose in normal NS rats, and actually a caused a slight increase in sucrose consumption and preference in male NS rats. Other measures that indicate depression - food intake and motor activity in the home cage - were also assessed. SwLo and SwHi showed greater sensitivity to having their home-cage ambulatory activity reduced by CMS than did NS rats, but no other such differences relative to NS rats were seen for these other measures; thus, changes in sucrose intake or preference could not be explained by a change in caloric intake. These results suggest that the genetic attributes of animals can influence the outcome of CMS, and that the application of CMS to normal, non-selected rats may account, at least in part, for the unreliability of CMS in decreasing consumption of palatable substances and decreasing preference for such substances. (C) 2013 Published by Elsevier Inc.
• Continuation of structure–activity relationship study of novel benzamide derivatives as potential antipsychotics
  作者：Mingshuo Xu、Shuang Guo、Feipu Yang、Yu Wang、Chunhui Wu、Xiangrui Jiang、Qingjie Zhao、Weiming Chen、Guanghui Tian、Fuqiang Zhu、Yuanchao Xie、Tianwen Hu、Zhen Wang、Yang He、Jingshan Shen

  DOI：10.1002/ardp.201800306

  日期：2019.4

  of benzamide derivatives possessing potent dopamine D2, serotonin 5‐HT1A, and 5‐HT2A receptor properties were synthesized and evaluated as potential antipsychotics. Among them, 5‐(4‐(4‐(benzo[d]isothiazol‐3‐yl)piperazin‐1‐yl)butoxy)‐N‐cyclopropyl‐2‐fluorobenzamide (4k) held the best pharmacological profile. It not only exhibited potent and balanced activities for the D2, 5‐HT1A, and 5‐HT2A receptors

  合成了一系列具有强效多巴胺 D2、5-羟色胺 5-HT1A 和 5-HT2A 受体特性的苯甲酰胺衍生物，并将其评估为潜在的抗精神病药。其中，5-(4-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)butoxy)-N-cyclopropyl-2-fluorobenzamide (4k) 具有最好的药理学特征。它不仅对 D2、5-HT1A 和 5-HT2A 受体表现出强效和平衡的活性，而且对 5-HT2C、H1 和 M3 受体也具有低至中度的活性，这表明其诱导体重的倾向较低增益或糖尿病。在动物模型中，化合物 4k 减少了苯环利定诱导的多动症，具有高阈值的僵住症或肌肉松弛诱导。基于其在精神分裂症临床前模型中的强大体外效力和体内功效，