N-methyl-N-cyclohexyl-p-(amino)phenethylamine

• 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-methyl-N-cyclohexyl-p-(amino)phenethylamine
• 英文别名: 4-(2-(N-cyclohexyl-N-methyl)aminoethyl)aniline；4-[2-[Cyclohexyl(methyl)amino]ethyl]aniline
• 化学式: C₁₅H₂₄N₂
• 分子量: 232.369
• InChiKey: RTSRUXDHCMBLNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  草酰氯 、 7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxylic acid 、 N-methyl-N-cyclohexyl-p-(amino)phenethylamine 在 三乙胺 作用下， 以 四氢呋喃 、 N-甲基乙酰胺 、 二氯甲烷 、 水 为溶剂， 生成 N-(4-(2-((N-cyclohexyl-N-methyl)amino)ethyl)phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide
  参考文献：
  名称：

  US6166006

  摘要：

  公开号：
• 作为产物：
  描述：

  N-methyl-N-cyclohexyl-p-nitrophenethylamine hydrochloride 在 盐酸 、 ammonium chloride 、 铁粉 作用下， 以 丙酮 为溶剂， 生成 N-methyl-N-cyclohexyl-p-(amino)phenethylamine
  参考文献：
  名称：

  New p-Methylsulfonamido Phenylethylamine Analogues as Class III Antiarrhythmic Agents:  Design, Synthesis, Biological Assay, and 3D-QSAR Analysis

  摘要：

  Class III antiarrhythmic agents selectively delay the effective refractory period (ERP) and increase the transmembrance action potential duration (APD). Using dofetilide (2) as a template of class III antiarrhythmic agents, we designed and synthesized 16 methylsulfonamido phenylethylamine analogues (4a-d and 5a-1). Pharmacological assay indicated that all of these compounds showed activity for increasing the ERP in isolated animal atrium; among them, the effective concentration of compound 4a is 1.6 x 10(-8) mol/L in increasing ERP by 10 ms, slightly less potent than that of 2, 1.1 x 10(-8) mol/L. Compound 4a also produced a slightly lower change in ERP at 10(-5) M, DeltaERP% = 17.5% (DeltaERP% = 24.0% for dofetilide). On the basis of this bioassay result, these 16 compounds together with dofetilide were investigated by the three-dimensional quantitative structure-activity relationship (3D-QSAR) techniques of comparative molecular field analysis (CoMFA), comparative molecular similarity index analysis (CoMSIA), and the hologram QSAR (HQSAR). The 3D-QSAR models were tested with another 11 compounds (4e-h and 5m-s) that we synthesized later. Results revealed that the CoMFA, CoMSIA, and HQSAR predicted activities for the 11 newly synthesized compounds that have a good correlation with their experimental value, r(2) = 0.943, 0.891, and 0.809 for the three QSAR models, respectively. This indicates that the 3D-QSAR models proved a good predictive ability and could describe the steric, electrostatic, and hydrophobic requirements for recognition forces of the receptor site. On the basis of these results, we designed and synthesized another eight new analogues of methanesulfonamido phenylethyamine (6a-h) according to the clues provided by the 3D-QSAR analyses. Pharmacological assay indicated that the effective concentrations of delaying the ERP by 10 ins of these newly designed compounds correlated well with the 3D-QSAR predicted values. It is remarkable that the percent change of delaying ERP at 10-5 M compound 6c is much higher than that of dofetilide; the effective concentration of compound 6c is 5.0 x 10(-8)mol/L in increasing the ERP by 10 Ms, which is slightly lower than that of 2. The results showed that the 3D-QSAR models are reliable and can be extended to design new antiarrhythmic agents.

  DOI：

  10.1021/jm010574u

文献信息

• [EN] ANILIDE DERIVATIVE, PRODUCTION AND USE THEREOF<br/>[FR] DERIVE D'ANILIDE, SA PREPARATION ET SON UTILISATION
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：WO1999032468A1

  公开（公告）日：1999-07-01

  (EN) This invention is provide a compound of formula (I) wherein R1 is an optionally substituted 5- to 6-membered ring; W is a divalent group of formula (a) or (b) wherein the ring A is an optionally substituted 5- to 6-membered aromatic ring, X is an optionally substituted C, N or O atom, and the ring B is an optionally substituted 5- to 7-membered ring; Z is a chemical bond or a divalent group; R2 is (1) an optionally substituted amino group in which a nitrogen atom may form a quaternary ammonium, etc., or a salt thereof, which is useful for antagonizing MCP-1 receptor.(FR) L'invention concerne un composé représenté par la formule (I): dans laquelle R1 représente un noyau éventuellement substitué de 5 à 6 éléments; W représente un groupe divalent de formule (a) ou (b): ou dans laquelle le noyau A est un noyau aromatique éventuellement substitué de 5 à 6 éléments; X représente un atome de C, N ou O éventuellement substitué et le noyau B est un noyau éventuellement substitué de 5 à 6 éléments; Z représente une liaison chimique ou un groupe divalent; R2 représente (1) un groupe amino éventuellement substitué dans lequel un atome d'azote peut constituer un ammonium quaternaire, etc., ou un de ses sels, utile en tant qu'antagoniste du récepteur MCP-1.

  该发明提供了一个公式（I）的化合物，其中R1是一个可选取代的5-至6-成员环；W是公式（a）或（b）的二价基团，其中环A是一个可选取代的5-至6-成员芳香环，X是一个可选取代的C、N或O原子，环B是一个可选取代的5-至7-成员环；Z是一个化学键或二价基团；R2是（1）一个可选取代的氨基基团，其中氮原子可以形成季铵盐等，或其盐，对拮抗MCP-1受体有用。
• ANILIDE DERIVATIVE, PRODUCTION AND USE THEREOF
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1040103B1

  公开（公告）日：2007-03-14
• US6172061B1
  申请人：——

  公开号：US6172061B1

  公开（公告）日：2001-01-09
• US6166006A
  申请人：——

  公开号：US6166006A

  公开（公告）日：2000-12-26
• US6268354B1
  申请人：——

  公开号：US6268354B1

  公开（公告）日：2001-07-31