[1-(4-氟苯基)环己基]甲胺盐酸盐 | 771583-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [1-(4-氟苯基)环己基]甲胺盐酸盐
• 中文别名: 1-(4-氟苯基)环己烷甲胺
• 英文名称: 1-[1-(4-fluorophenyl)cyclohexyl]methylamine
• 英文别名: [1-(4-fluorophenyl)cyclohexyl]methanamine；(1-(4-fluorophenyl)cyclohexyl)methanamine
• CAS: 771583-24-5
• 化学式: C₁₃H₁₈FN
• 分子量: 207.291
• InChiKey: VPDDMTHLPLVCMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  [1-(4-氟苯基)环己基]甲胺盐酸盐 在 盐酸 、 sodium acetate 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.0h， 生成 1-benzyl-N-{[1-(4-fluorophenyl)cyclohexyl]methyl}piperidine-4-carboxamide hydrochloride
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 1-alkyl-N-[2-ethyl-2-(4-fluorophenyl)butyl]piperidine-4-carboxamide derivatives as novel antihypertensive agents

  摘要：

  We synthesized and evaluated inhibitory activity against T-type Ca(2+) channels for a series of 1-alkyl-N-[2-ethyl-2-(4-fluorophenyl)butyl]piperidine-4-carboxamide derivatives. Structure-activity relationship studies have revealed that dialkyl substituents at the benzylic position play an important role in increasing inhibitory activity. Oral administration of N-[2-ethyl-2-(4-fluorophenyl)butyl]-1-(2-phenylethyl)piperidine-4-carboxamide (20d) lowered blood pressure in spontaneously hypertensive rats without inducing reflex tachycardia, which is often caused by traditional L-type Ca(2+) channel blockers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.030
• 作为产物：
  描述：

  1-(4-氟苯基)环己烷甲腈 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 以70.3 %的产率得到[1-(4-氟苯基)环己基]甲胺盐酸盐
  参考文献：
  名称：

  4-氟苯基环己基(四氢吡喃基)甲基取代芳氧基丙醇胺的合成及生物活性

  摘要：

  摘要 (4-氟苯基)乙腈用二溴戊烷和2,2'-二氯二乙醚烷基化，得到相应的腈，再用氢化铝锂还原，得到[1-(4-氟苯基)环己基]-和[1-(4-氟苯基)四氢-2H-吡喃-4-基]甲胺。用芳环上取代的芳氧基甲基环氧乙烷处理后一产物，合成了 。部分合成的芳氧基丙醇胺在福尔马林的作用下转化为相应的恶唑烷。

  DOI：

  10.1134/s1070428023050020

文献信息

• Cycloalkylamines as monoamine reuptake inhibitors
  申请人：Shao Liming

  公开号：US20070203111A1

  公开（公告）日：2007-08-30

  The invention relates to novel cyclohexylamine derivatives and their use in the treatment and/or prevention of central nervous system (CNS) disorders, such as depression, anxiety, schizophrenia and sleep disorder as well as methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention, as well as methods of inhibiting reuptake of endogenous monoamines, such as dopamine, serotonin and norepinephrine from the synaptic cleft and methods of modulating one or more monoamine transporter.

  本发明涉及新型环己胺衍生物及其在中枢神经系统（CNS）疾病的治疗和/或预防中的应用，例如抑郁症、焦虑症、精神分裂症和睡眠障碍，以及它们的合成方法。本发明还涉及包含本发明化合物的制药组合物，以及抑制内源性单胺，如多巴胺、5-羟色胺和去甲肾上腺素从突触间隙中再摄取的方法和调节一个或多个单胺转运体的方法。
• CYCLOALKYLAMINES AS MONOAMINE REUPTAKE INHIBITORS
  申请人：Shao Liming

  公开号：US20100190861A1

  公开（公告）日：2010-07-29

  The invention relates to novel cyclohexylamine derivatives and their use in the treatment and/or prevention of central nervous system (CNS) disorders, such as depression, anxiety, schizophrenia and sleep disorder as well as methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention, as well as methods of inhibiting reuptake of endogenous monoamines, such as dopamine, serotonin and norepinephrine from the synaptic cleft and methods of modulating one or more monoamine transporter.

  本发明涉及新型环己基胺衍生物及其在治疗和/或预防中枢神经系统（CNS）疾病方面的应用，例如抑郁症，焦虑症，精神分裂症和睡眠障碍，以及它们的合成方法。本发明还涉及含有本发明化合物的制药组合物，以及抑制内源性单胺，如多巴胺，5-羟色胺和去甲肾上腺素从突触间隙中再摄取的方法，以及调节一个或多个单胺转运体的方法。
• Novel 3-(1H-indol-3-yl)-2-[3-(4-methoxyphenyl)ureido]propanamides as selective agonists of human formyl-peptide receptor 2
  作者：Enza Lacivita、Igor A. Schepetkin、Madia L. Stama、Liliya N. Kirpotina、Nicola A. Colabufo、Roberto Perrone、Andrei I. Khlebnikov、Mark T. Quinn、Marcello Leopoldo

  DOI：10.1016/j.bmc.2014.12.007

  日期：2015.7

  N-Formyl peptide receptors (FPRs) are G protein-coupled receptors (GPCRs) that play critical roles in inflammatory reactions, and FPR-specific interactions can possibly be used to facilitate the resolution of pathological inflammatory reactions. We here report the synthesis and biological evaluation of six pairs of chiral ureidopropanamido derivatives as potent and selective formyl peptide receptor-2 (FPR2) agonists that were designed starting from our lead agonist (S)-3-(1H-indol-3-yl)-2-[3-(4-methoxyphenyl)ureido]-N-[[1-(5-methoxy-2-pyridinyl)cyclohexyl]methyl]propanamide ((S)-9a). The new compounds were obtained in overall yields considerably higher than (S)-9a. Several of the new compounds showed agonist properties comparable to that of (S)-9a along with higher selectivity over FPR1. Molecular modeling was used to define chiral recognition by FPR2. In vitro metabolic stability of selected compounds was also assessed to obtain preliminary insight on drug-like properties of this class of compounds. (C) 2014 Elsevier Ltd. All rights reserved.
• Discovery of N-methyl-1-(1-phenylcyclohexyl)methanamine, a novel triple serotonin, norepinephrine, and dopamine reuptake inhibitor
  作者：Liming Shao、Michael C. Hewitt、Fengjiang Wang、Scott C. Malcolm、Jianguo Ma、John E. Campbell、Una C. Campbell、Sharon R. Engel、Nancy A. Spicer、Larry W. Hardy、Rudy Schreiber、Kerry L. Spear、Mark A. Varney

  DOI：10.1016/j.bmcl.2011.01.016

  日期：2011.3

  The current work discloses a novel cyclohexylarylamine chemotype with potent inhibition of the serotonin, norepinephrine, and dopamine transporters and potential for treatment of major depressive disorder. Optimized compounds 1 (SERT, NET, DAT, IC50 = 169, 85, 21 nM) and 42 (SERT, NET, DAT IC50 = 34, 295, 90 nM) were highly brain penetrant, active in vivo in the mouse tail suspension test at 30 mpk po and were not general motor stimulants. (C) 2011 Elsevier Ltd. All rights reserved.
• US8877975B2
  申请人：——

  公开号：US8877975B2

  公开（公告）日：2014-11-04