3-dimethylamino-1-(2-naphthyl)propanamine | 917351-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-dimethylamino-1-(2-naphthyl)propanamine
• 英文别名: N',N'-dimethyl-1-naphthalen-2-ylpropane-1,3-diamine
• CAS: 917351-50-9
• 化学式: C₁₅H₂₀N₂
• mdl: MFCD25679776
• 分子量: 228.337
• InChiKey: PNVBYQXJFNMJDW-UHFFFAOYSA-N

物化性质

• 沸点：
  370.7±30.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-1-(2-naphthyl)propanamine 、 反式-4-甲氧基肉桂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以47%的产率得到N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-methoxycinnamamide
  参考文献：
  名称：

  Design, parallel synthesis and SAR of novel urotensin II receptor agonists

  摘要：

  A 30-membered library of amides based on the potent urotensin II (UII) receptor agonist FL104, has been synthesized from ten different carboxylic acids and three amines. A synthetic protocol producing the amides in 47-98% yield has been developed in which the purification involved only extractions and in a few cases filtration through an ion-exchange resin. It was found that 5 mg of starting material was enough to obtain reproducible results and excellent purities. Thus, the procedure is estimated to be transferable to fully automated systems. The synthesized compounds were evaluated for their Ull receptor agonistic activities using a cell-based assay (R-SAT). The most active compounds were the 4-trifluoromethylcinnamic amides of 1-(4-chlorophenyt)-3-dimethylamino-propylamine and 1-(2-naphthyl)-3-dimethylamino-propylamine, both showed EC50 values of 130 nM. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.015
• 作为产物：
  描述：

  N-[3-(dimethylamino)-1-naphthalen-2-ylpropyl]acetamide 在 盐酸 作用下， 反应 72.0h， 生成 3-dimethylamino-1-(2-naphthyl)propanamine
  参考文献：
  名称：

  Design, parallel synthesis and SAR of novel urotensin II receptor agonists

  摘要：

  A 30-membered library of amides based on the potent urotensin II (UII) receptor agonist FL104, has been synthesized from ten different carboxylic acids and three amines. A synthetic protocol producing the amides in 47-98% yield has been developed in which the purification involved only extractions and in a few cases filtration through an ion-exchange resin. It was found that 5 mg of starting material was enough to obtain reproducible results and excellent purities. Thus, the procedure is estimated to be transferable to fully automated systems. The synthesized compounds were evaluated for their Ull receptor agonistic activities using a cell-based assay (R-SAT). The most active compounds were the 4-trifluoromethylcinnamic amides of 1-(4-chlorophenyt)-3-dimethylamino-propylamine and 1-(2-naphthyl)-3-dimethylamino-propylamine, both showed EC50 values of 130 nM. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.015

文献信息

• Novel and potent small-molecule urotensin II receptor agonists
  作者：Fredrik Lehmann、Erika A. Currier、Bryan Clemons、Lars K. Hansen、Roger Olsson、Uli Hacksell、Kristina Luthman

  DOI：10.1016/j.bmc.2009.04.062

  日期：2009.7

  A series of analogs of the non-peptidic urotensin II receptor agonist N-[1-(4-chlorophenyl)-3-(dimethylamino)propyl]-4-phenylbenzamide (FL104) has been synthesized and evaluated pharmacologically. The enantiomers of the two most potent racemic analogues were obtained from the corresponding diastereomeric mandelic amides. In agreement with previously observed SAR, most of the agonist potency resided

  已经合成了一系列非肽尿紧张素II受体激动剂N- [1-（4-氯苯基）-3-（二甲基氨基）丙基] -4-苯基苯甲酰胺（FL104）的类似物，并进行了药理学评价。两种最有效的外消旋类似物的对映异构体获自相应的非对映体扁桃酰胺。与先前观察到的SAR一致，大多数激动剂效力存在于（S）对映异构体中。新系列中最有效的UII受体激动剂是（S）-N- [3-二甲基氨基-1-（2-萘基丙基）丙基] -4-（4-氯苯基）苯甲酰胺（ 在尿紧张素II处EC 50 = 23 nM受体）。
• UII-modulating compounds and their use
  申请人：Luthman Kristina Ingrid

  公开号：US20070043104A1

  公开（公告）日：2007-02-22

  Disclosed herein are novel aromatic-containing compounds and methods for using various aromatic-containing compounds for treatment and prevention of diseases and disorders related to the Urotensin II receptor.

  本文披露了新型芳香族含有化合物及其在治疗和预防与Urotensin II受体相关的疾病和疾病障碍方面的应用方法。
• WO2006/135694
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] UII-MODULATING COMPOUNDS AND THEIR USE<br/>[FR] COMPOSES MODULATEURS D'UII ET UTILISATION
  申请人：ACADIA PHARM INC

  公开号：WO2006135694A2

  公开（公告）日：2006-12-21

  [EN] Disclosed herein are novel aromatic-containing compounds and methods for using various aromatic-containing compounds for treatment and prevention of diseases and disorders related to the Urotensin II receptor.
  [FR] Composés à éléments aromatiques et procédés d'utilisation concernant divers composés de ce type pour le traitement et la prévention de maladies et de troubles liés au récepteur d'urotensine II.
• [EN] UII-MODULATING COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS MODULANT U II ET LEUR UTILISATION
  申请人：ACADIA PHARM INC

  公开号：WO2008057543A2

  公开（公告）日：2008-05-15

  [EN] Disclosed herein are novel aromatic-containing compounds and methods for using various aromatic-containing compounds for treatment and prevention of diseases and disorders related to the Urotensin II receptor.
  [FR] La présente invention concerne de nouveaux composés contenant un groupe aromatique et des procédés permettant d'utiliser divers composés contenant un groupe aromatique pour le traitement et la prévention de maladies et de troubles associés au récepteur de l'urotensine II.