3-(trifluoromethyl)phenylcarbamoylchloride

• 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-(trifluoromethyl)phenylcarbamoylchloride
• 英文别名: N-[3-(trifluoromethyl)phenyl]carbamoyl chloride
• 化学式: C₈H₅ClF₃NO
• 分子量: 223.582
• InChiKey: UREXDAPKGATDPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-苯基-1-(2-苯乙基)-4-哌啶胺 、 3-(trifluoromethyl)phenylcarbamoylchloride 在 三乙胺 作用下， 生成 1-(1-phenethylpiperidin-4-yl)-1-phenyl-3-(3-(trifluoromethyl)phenyl)urea
  参考文献：
  名称：

  Evaluation of the analgesic effect of 4-anilidopiperidine scaffold containing ureas and carbamates

  摘要：

  Fentanyl is a powerful opiate analgesic typically used for the treatment of severe and chronic pain, but its prescription is strongly limited by the well-documented side-effects. Different approaches have been applied to develop strong analgesic drugs with reduced pharmacologic side-effects. One of the most promising is the design of multitarget drugs. In this paper we report the synthesis, characterization and biological evaluation of twelve new 4-anilidopiperidine (fentanyl analogues). In vivo hot-Plate test, shows a moderate antinociceptive activity for compounds OMDM585 and OMDM586, despite the weak binding affinity on both mu and delta-opioid receptors. A strong inverse agonist activity in the GTP-binding assay was revealed suggesting the involvement of alternative systems in the brain. Fatty acid amide hydrolase inhibition was evaluated, together with binding assays of cannabinoid receptors. We can conclude that compounds OMDM585 and 586 are capable to elicit antinociception due to their multitarget activity on different systems involved in pain modulation.

  DOI：

  10.3109/14756366.2016.1160902
• 作为产物：
  描述：

  光气 、 间氨基三氟甲苯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 3-(trifluoromethyl)phenylcarbamoylchloride
  参考文献：
  名称：

  Evaluation of the analgesic effect of 4-anilidopiperidine scaffold containing ureas and carbamates

  摘要：

  Fentanyl is a powerful opiate analgesic typically used for the treatment of severe and chronic pain, but its prescription is strongly limited by the well-documented side-effects. Different approaches have been applied to develop strong analgesic drugs with reduced pharmacologic side-effects. One of the most promising is the design of multitarget drugs. In this paper we report the synthesis, characterization and biological evaluation of twelve new 4-anilidopiperidine (fentanyl analogues). In vivo hot-Plate test, shows a moderate antinociceptive activity for compounds OMDM585 and OMDM586, despite the weak binding affinity on both mu and delta-opioid receptors. A strong inverse agonist activity in the GTP-binding assay was revealed suggesting the involvement of alternative systems in the brain. Fatty acid amide hydrolase inhibition was evaluated, together with binding assays of cannabinoid receptors. We can conclude that compounds OMDM585 and 586 are capable to elicit antinociception due to their multitarget activity on different systems involved in pain modulation.

  DOI：

  10.3109/14756366.2016.1160902

文献信息

• FLUORINE ATOM-CONTAINING COMPOUND AND USE THEREOF
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US20190031600A1

  公开（公告）日：2019-01-31

  Provided is a fluorine atom-containing compound represented by formula (1) below (In the formula, Z represents a predetermined divalent group, each Ar independently represents a predetermined aromatic ring-containing group, and each Ar F independently represents a predetermined fluorine atom-containing aryl group).

  提供的是下面公式（1）所代表的含氟原子的化合物（在公式中，Z代表预定的二价基团，每个Ar独立代表预定的含芳香环的基团，每个ArF独立代表预定的含氟原子的芳基基团）。
• Fluorine atom-containing compound and use thereof
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US10336686B2

  公开（公告）日：2019-07-02

  Provided is a fluorine atom-containing compound represented by formula (1) below (In the formula, Z represents a predetermined divalent group, each Ar independently represents a predetermined aromatic ring-containing group, and each ArF independently represents a predetermined fluorine atom-containing aryl group).

  本发明提供了由下式（1）表示的含氟原子化合物 (式中，Z 代表预定的二价基团，每个 Ar 独立地代表预定的含芳香环基团，每个 ArF 独立地代表预定的含氟原子的芳基）。
• Synthesis and biological evaluation of piperazine-based derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
  作者：Bin Ye、Yuo-Ling Chou、Rushad Karanjawala、Wheeseong Lee、Shou-Fu Lu、Kenneth J. Shaw、Steven Jones、Dao Lentz、Amy Liang、Jih-Lie Tseng、Qingyu Wu、Zuchun Zhao

  DOI：10.1016/j.bmcl.2003.11.035

  日期：2004.2

  Compound 2 was identified by high throughput screening as a novel PAI-1 inhibitor. Systematic optimization of the A, B, and C segments of 2 resulted in the identification of a more potent compound 39 with good oral bioavailability. The synthesis and SAR data are presented in this report. (C) 2003 Elsevier Ltd. All rights reserved.
• Evaluation of the analgesic effect of 4-anilidopiperidine scaffold containing ureas and carbamates
  作者：Ludovica Monti、Azzurra Stefanucci、Stefano Pieretti、Francesca Marzoli、Lorenzo Fidanza、Adriano Mollica、Sako Mirzaie、Simone Carradori、Luciano De Petrocellis、Aniello Schiano Moriello、Sándor Benyhe、Ferenc Zádor、Edina Szűcs、Ferenc Ötvös、Anna I. Erdei、Reza Samavati、Szabolcs Dvorácskó、Csaba Tömböly、Ettore Novellino

  DOI：10.3109/14756366.2016.1160902

  日期：2016.11.1

  Fentanyl is a powerful opiate analgesic typically used for the treatment of severe and chronic pain, but its prescription is strongly limited by the well-documented side-effects. Different approaches have been applied to develop strong analgesic drugs with reduced pharmacologic side-effects. One of the most promising is the design of multitarget drugs. In this paper we report the synthesis, characterization and biological evaluation of twelve new 4-anilidopiperidine (fentanyl analogues). In vivo hot-Plate test, shows a moderate antinociceptive activity for compounds OMDM585 and OMDM586, despite the weak binding affinity on both mu and delta-opioid receptors. A strong inverse agonist activity in the GTP-binding assay was revealed suggesting the involvement of alternative systems in the brain. Fatty acid amide hydrolase inhibition was evaluated, together with binding assays of cannabinoid receptors. We can conclude that compounds OMDM585 and 586 are capable to elicit antinociception due to their multitarget activity on different systems involved in pain modulation.