N,N-dimethyl-γ-(3-nitrophenoxy)-benzene-propanamine | 72084-03-8

• 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: N,N-dimethyl-γ-(3-nitrophenoxy)-benzene-propanamine
• 英文别名: N,N-dimethyl-gamma-(3-nitrophenoxy)-benzene-propanamine；N,N-dimethyl-3-(3-nitrophenoxy)-3-phenylpropan-1-amine
• CAS: 72084-03-8
• 化学式: C₁₇H₂₀N₂O₃
• 分子量: 300.357
• InChiKey: NICLOXVBCUUCGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-γ-(3-nitrophenoxy)-benzene-propanamine 在 platinum(IV) oxide 、 叠氮磷酸二苯酯 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 1-[3-[3-(Dimethylamino)-1-phenylpropoxy]phenyl]-3-(1-methylindol-5-yl)urea
  参考文献：
  名称：

  Design of novel multiple-acting ligands towards SERT and 5-HT2C receptors

  摘要：

  This Letter describes our attempts to elaborate dually acting compounds possessing serotonin re-uptake transporter inhibitor and serotonin 5-HT2C receptor antagonist properties. A novel series of 1,3-diphenylureas and N-phenylbenzamides have thus been prepared and evaluated. Based on its in vitro and in vivo activities, as well as pharmacokinetic profile, compound 16a was identified as a lead compound. The synthesis and structure-activity relationship of this series of compounds is presented herein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.043
• 作为产物：
  描述：

  3-二甲基氨基-1-苯丙烷-1-酮 在 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 N,N-dimethyl-γ-(3-nitrophenoxy)-benzene-propanamine
  参考文献：
  名称：

  Design of novel multiple-acting ligands towards SERT and 5-HT2C receptors

  摘要：

  This Letter describes our attempts to elaborate dually acting compounds possessing serotonin re-uptake transporter inhibitor and serotonin 5-HT2C receptor antagonist properties. A novel series of 1,3-diphenylureas and N-phenylbenzamides have thus been prepared and evaluated. Based on its in vitro and in vivo activities, as well as pharmacokinetic profile, compound 16a was identified as a lead compound. The synthesis and structure-activity relationship of this series of compounds is presented herein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.043

文献信息

• 3-Aryloxy-3-aryl-propaneamines and their method of use
  申请人：Roussel Uclaf

  公开号：US04296126A1

  公开（公告）日：1981-10-20

  Novel benzene-propanamines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, chlorine, fluorine and bromine, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.2 is alkyl of 1 to 5 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, chlorine, bromine, --CF.sub.3, methyl and methoxy when R.sub.4 is nitro and R.sub.3 is selected from the group consisting of amino and acetamido when R.sub.4 is hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having anorexigenic activity and inhibit serotonine uptake in vivo and in vitro and their preparation.

  新型苯丙胺的化学式为##STR1##其中X从氢、氯、氟和溴组成的群体中选择，R.sub.1从氢和1至5个碳原子的烷基组成的群体中选择，R.sub.2是1至5个碳原子的烷基，R.sub.3从氢、氯、溴、--CF.sub.3、甲基和甲氧基组成的群体中选择，当R.sub.4是硝基时，R.sub.3从氨基和乙酰氨基组成的群体中选择，当R.sub.4是氢时，它们的无毒、药学上可接受的酸盐具有压食活性并在体内和体外抑制5-羟色胺摄取，以及它们的制备。
• US4296126A
  申请人：——

  公开号：US4296126A

  公开（公告）日：1981-10-20
• Design of novel multiple-acting ligands towards SERT and 5-HT2C receptors
  作者：Olivér Éliás、Éva Ágai-Csongor、György Domány、György Miklós Keserű、Anikó Gere、Béla Kiss、Éva Hellinger、Mónika Vastag、István Gyertyán

  DOI：10.1016/j.bmcl.2014.03.043

  日期：2014.5

  This Letter describes our attempts to elaborate dually acting compounds possessing serotonin re-uptake transporter inhibitor and serotonin 5-HT2C receptor antagonist properties. A novel series of 1,3-diphenylureas and N-phenylbenzamides have thus been prepared and evaluated. Based on its in vitro and in vivo activities, as well as pharmacokinetic profile, compound 16a was identified as a lead compound. The synthesis and structure-activity relationship of this series of compounds is presented herein. (C) 2014 Elsevier Ltd. All rights reserved.