3-Biphenylyl Chloroformate | 870555-09-2

• 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-Biphenylyl Chloroformate
• 英文别名: (3-phenylphenyl) carbonochloridate
• CAS: 870555-09-2
• 化学式: C₁₃H₉ClO₂
• 分子量: 232.666
• InChiKey: JCRKFGONEOKIMS-UHFFFAOYSA-N

物化性质

• 沸点：
  341.4±21.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Biphenylyl Chloroformate 、 5-羟基色胺盐酸盐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以63%的产率得到OMDM106
  参考文献：
  名称：

  New N-Arachidonoylserotonin Analogues with Potential “Dual” Mechanism of Action against Pain

  摘要：

  N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of alpha- and gamma-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbarnate 3f (OMDM 106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 mu M). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formal in-induced hyperalgesia in mice.

  DOI：

  10.1021/jm070678q
• 作为产物：
  描述：

  光气 、 间羟基联苯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 3-Biphenylyl Chloroformate
  参考文献：
  名称：

  Modulation of thermo-transient receptor potential (thermo-TRP) channels by thymol-based compounds

  摘要：

  A series of thirty-three thymol, p-cymene-3-carboxylic acid, and 3-amino-p-cymene derivatives was synthesized and tested on TRPA1, TRPM8, and TRPV3 channels. Most of them acted as strong modulators of TRPA1, TRPM8, and TRPV3 channels with EC50 and/or IC50 values distinctly lower than those of thymol and related monoterpenoids. Some of the compounds examined, that is, 3c, 4e, f, 6b, and 8b exhibited an appreciable subtype-selectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.055

文献信息

• Synthesis and SAR studies of 1,4-diazabicyclo[3.2.2]nonane phenyl carbamates – subtype selective, high affinity α7 nicotinic acetylcholine receptor agonists
  作者：Christopher J. O’Donnell、Langu Peng、Brian T. O’Neill、Eric P. Arnold、Robert J. Mather、Steven B. Sands、Alka Shrikhande、Lorraine A. Lebel、Douglas K. Spracklin、Frank M. Nedza

  DOI：10.1016/j.bmcl.2009.06.059

  日期：2009.8

  4-diazabicyclo[3.2.2]nonane phenyl carbamate series of α7 nAChR agonists is described. The development of the medicinal chemistry strategy and SAR which led to the identification of 5 and 7aa as subtype selective, high affinity α7 agonists as excellent leads for further evaluation is discussed, along with key physicochemical and pharmacokinetic data highlighting their lead potential.

  描述了有关α7nAChR激动剂的1,4-二氮杂双环[3.2.2]壬烷苯基氨基甲酸酯系列的双环胺，氨基甲酸酯连接基和芳环的合成和SAR研究。讨论了药物化学策略和SAR的发展，从而将5和7aa鉴定为亚型选择性，高亲和力α7激动剂，作为进一步评估的极好线索，并讨论了突出其潜在潜力的重要理化和药代动力学数据。
• Ketolide anti-infective compounds
  申请人：Li Yong

  公开号：US20050272672A1

  公开（公告）日：2005-12-08

  Compounds according to formula I wherein m is 0 or 1; X is and R 1 , R 2 , R 3 R 4 , and R 5 are as defined herein, are useful as anti-infective agents.

  根据公式I，化合物中m为0或1；X为，R1、R2、R3、R4和R5如下所定义，可用作抗感染剂。
• Tetrahydro-β-carboline derivatives targeting fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channels
  作者：Giorgio Ortar、Luciano De Petrocellis、Aniello Schiano Moriello、Marco Allarà、Enrico Morera、Marianna Nalli、Vincenzo Di Marzo

  DOI：10.1016/j.bmcl.2012.10.137

  日期：2013.1

  A series of twenty-five derivatives of tetrahydro-beta-carbolines 1-3 was synthesized and assayed on FAAH and TRPV1 and TRPA1 channels. Four carbamates, that is, 5a,c,e, and 9b inhibited FAAH with significant potency and interacted also effectively with TRPV1 and TRPA1 nociceptive receptors, while ureas 7b,d,f, and 8a,b were endowed with specific submicromolar TRPV1 modulating activities. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of piperazinyl carbamates and ureas as fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channel dual ligands
  作者：Enrico Morera、Luciano De Petrocellis、Ludovica Morera、Aniello Schiano Moriello、Alessia Ligresti、Marianna Nalli、David F. Woodward、Vincenzo Di Marzo、Giorgio Ortar

  DOI：10.1016/j.bmcl.2009.09.033

  日期：2009.12

  The evaluation of a series of piperazinyl carbamates and ureas, designed on the basis of previously reported TRPV1 antagonists and FAAH inhibitors, led to the identification of some 'dual-action' compounds targeting both FAAH and TRPV1 or TRPA1 receptors. (C) 2009 Elsevier Ltd. All rights reserved.
• US8063021B2
  申请人：——

  公开号：US8063021B2

  公开（公告）日：2011-11-22