N-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-4-nitrobenzamide | 179258-59-4

• 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-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-4-nitrobenzamide
• 英文别名: N-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-4nitro benzamide
• CAS: 179258-59-4
• 化学式: C₂₀H₂₅N₃O₅
• 分子量: 387.436
• InChiKey: XEAKAKKNLOUHDV-UHFFFAOYSA-N

物化性质

• 沸点：
  598.1±50.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-4-nitrobenzamide 在 BF4 超重氢 作用下， 以 二氯甲烷 为溶剂， 生成 N-[3-[2-(3,4-dimethoxyphenyl)ethylamino]propyl]-4-nitro-2,6-ditritiobenzamide
  参考文献：
  名称：

  Direct tritium labeling of multifunctional compounds using organoiridium catalysis. 2.

  摘要：

  A variety of complex compounds have been labeled with tritium gas by catalytic exchange in the presence of catalyst precursors [(cod)Ir(dppe)]BF4 or [(cod)Ir(py)(PCy3)]BF4. In most cases, predictable regioselectivity and high specific activities are achieved. These results are compared in some cases to the results of labeling related compounds with [(cod)Ir(PPh3)(2)]BF4. Prereduction of the catalyst precursors in situ with hydrogen allows the use of smaller quantities of tritium gas and reduces the amount of radioactive waste. Two or more compounds can be labeled simultaneously as mixtures then separated in the HPLC purification step to increase compound throughput.

  DOI：

  10.1002/(sici)1099-1344(199908)42:8<797::aid-jlcr240>3.0.co;2-o
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 、 N-3-chloropropyl-4-nitrobenzamide 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 N-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-4-nitrobenzamide
  参考文献：
  名称：

  Synthesis, electrophysiological properties and analysis of structural requirements of a novel class of antiarrhythmic agents with potassium and calcium channel blocking properties

  摘要：

  Class III antiarrhythmic agents have been shown to prevent reentrant arrhythmias but also to be responsible for initiating arrhythmias characterised by afterdepolarizations and triggered activities. By combining potassium and calcium channel antagonistic actions, as with BRL-32872(1,2) (1), it might be possible to reduce the incidence of proarrhythmias albeit retaining antiarrhythmic efficacy. In the present study we synthesised and tested for their electrophysiological activity in guinea pig papillary muscle a wide panel of analogues of BRL-32872. Some qualitative relationships between compound structure and the inhibitory effect on the rapidly activating component of the delayed rectifier potassium current and/or the L-type calcium current will be presented. New derivatives depicting bell-shaped dose-response curves on action potential duration may therefore represent novel agents for improved antiarrhythmic therapy. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00166-7

文献信息

• [EN] NITRO-BENZAMIDES USEFUL AS ANTI-ARRHYTHMIC AGENTS<br/>[FR] NITRO-BENZAMIDES UTILISABLES COMME AGENTS ANTIARYTHMIQUES
  申请人：SMITHKLINE BEECHAM LABORATOIRES PHARMACEUTIQUES

  公开号：WO1996013479A1

  公开（公告）日：1996-05-09

  (EN) A compound of formula (I), or a salt thereof, or a solvate thereof, wherein Ar represents substituted or unsubstituted aryl, wherein the optional substituents are selected from alkyl, hydroxy or alkoxy or, if attached to adjacent carbon atoms any two substituents together with the carbon atoms to which they are attached may form a fused heterocyclic ring of five to six atoms wherein one, two or three of the said atoms are oxygen or nitrogen; A represents a C1-4n-alkylene group wherein each carbon is optionally substituted by 1 or 2 C1-6alkyl groups; R1 represents hydrogen, alkyl, alkenyl or cycloalkyl; one or two of the group of R2, R3 and R4 represents nitro the remaining members of the group of R2, R3 and R4 represent hydrogen; X represents a -CO-NH- moiety; and Z represents C2-4n-alkylene group wherein each carbon is optionally substituted 1 or 2 C1-6alkyl groups; a process for preparing such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.(FR) Composé répondant à la formule (I), ou son sel ou solvate, dans laquelle Ar représente aryle éventuellement substitué, les éventuels substituants étant choisis parmi alkyle, hydroxy et alcoxy ou, s'ils sont rattachés aux atomes de carbone adjacents, deux substituants, pris ensemble avec les atomes de carbone auxquels ils sont rattachés, peuvent former un hétérocycle condensé à cinq ou six atomes dont un, deux ou trois sont des atomes d'oxygène ou d'azote; A représente un groupe n-alkylène C1-4 dans lequel chaque atome de carbone est éventuellement substitué par 1 ou 2 groupes alkyle C1-6; R1 représente hydrogène, alkyle, alcényle ou cycloalkyle; un ou deux éléments du groupe constitué de R2, R3 et R4 représente(nt) nitro, et les éléments restants du groupe constitué de R2, R3 et R4 représentent hydrogène; X représente une fraction -CO-NH-; et Z représente un groupe n-alkylène C2-4 dans lequel chaque atome de carbone est éventuellement substitué par 1 ou 2 groupes alkyle C1-6; procédé de préparation de composés de ce type, compositions pharmaceutiques comportant de tels composés, et application de ceux-ci en médecine.

  化合物式(I)的化合物，或其盐或溶剂化物，其中Ar代表取代或未取代的芳基，其中可选的取代基从烷基，羟基或烷氧基中选择，或者如果与相邻的碳原子连接，则任意两个取代基与它们连接的碳原子可以形成一个由五到六个原子组成的融合杂环环，其中其中一个，两个或三个原子是氧或氮; A代表C1-4n-烷基，其中每个碳原子可以选择性地被1或2个C1-6烷基取代; R1代表氢，烷基，烯基或环烷基; R2，R3和R4组成的一个或两个元素代表硝基，其余的元素代表氢; X代表-CO-NH-部分; Z代表C2-4n-烷基，其中每个碳原子可以选择性地被1或2个C1-6烷基取代; 一种制备这种化合物的方法，包含这种化合物的药物组合物以及这种化合物在医学上的用途。
• Nitro-benzamides useful as anti-arrhythmic agents
  申请人：SmithKline Beecham p.l.c.

  公开号：US20010025054A1

  公开（公告）日：2001-09-27

  A compound of formula (I): or a salt thereof, or a solvate thereof, wherein Ar represents substituted or unsubstituted aryl, wherein the optional substituents are selected from alkyl, hydroxy or alkoxy or, if attached to adjacent carbon atoms any two substituents together with the carbon atoms to which they are attached may form a fused heterocyclic ring of five to six atoms wherein one, two or three of the said atoms are oxygen or nitrogen; A represents a C 1-4 n-alkylene group wherein each carbon is optionally substituted by 1 or 2 C 1-6 alkyl groups; R 1 represents hydrogen, alkyl, alkenyl or cycloalkyl; one or two of of the group of R 2 , R 3 and R 4 represents nitro the remaining members of the group of R 2 , R 3 and R 4 represent hydrogen; X represents a —CO—NH— moiety; and Z represents C 2-4 n-alkylene group wherein each carbon is optionally substituted 1 or 2 C 1-6 alkyl groups; a process for preparing such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  化合物的式子（I）：或其盐，或其溶剂化物，其中Ar代表取代或未取代的芳基，其中可选的取代基来自烷基，羟基或烷氧基，或者如果连接到相邻的碳原子，任意两个取代基与它们所连接的碳原子一起可以形成一个由五到六个原子组成的融合杂环环，其中一个、两个或三个原子是氧或氮；A代表C1-4n-烷基，其中每个碳原子可以选择地被1或2个C1-6烷基所取代；R1代表氢，烷基，烯基或环烷基；R2，R3和R4中的一或两个代表硝基，R2，R3和R4组的其余成员代表氢；X代表-CO-NH-基团；Z代表C2-4n-烷基，其中每个碳可以选择地被1或2个C1-6烷基所取代；制备这种化合物的方法，包括这种化合物的制药组成物以及在医学上使用这种化合物。
• Nitro-benzamide useful as anti-arrhythmic agent
  申请人：SmithKline Beecham p.l.c.

  公开号：US20010056207A1

  公开（公告）日：2001-12-27

  Hydrated N-[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-4-nitro benzamide hydrochloride characterized in that it: (i) comprises water in the range of from 1.7 to 2.4 molar equivalents; and/or (ii) has a melting point above 145° C. and/or (iii) provides an infra red spectrum containing peaks at 3510, 3342, 3076, 1665, 1598, 1343, 1330, 1216 and 801 cm −1 ; and/or (iv) provides a solid state nuclear magnetic resonance spectrum containing chemical shifts substantially as represented in Table I; and/or (v) provides an X-ray powder refraction (XRPD) pattern substantially as represented in Table II; a process for preparing such a compound, a pharmaceutical composition comprising such a compound and the use of such a compound in medicine.

  水合的N-[3-[[2-(3,4-二甲氧基苯基)乙基]氨基]丙基]-4-硝基苯甲酰胺盐酸盐的特征在于：(i) 包含1.7至2.4摩尔当量的水；和/或(ii) 具有高于145℃的熔点；和/或(iii) 提供红外光谱，其中包含3510、3342、3076、1665、1598、1343、1330、1216和801 cm^-1的峰；和/或(iv) 提供固态核磁共振光谱，其中化学位移基本如表I所示；和/或(v) 提供X射线粉末衍射（XRPD）图案，基本如表II所示；制备此化合物的方法，包括此化合物的药物组合物以及在医学中使用此化合物的用途。
• Nitro-benzamides useful as Anti-arrhythmic agents
  申请人：SmithKline Beecham Laboratoires Pharmaceutiques

  公开号：US20020107243A1

  公开（公告）日：2002-08-08

  A compound of formula (I): or a salt thereof, or a solvate thereof, wherein Ar represents substituted or unsubstituted aryl, wherein the optional substituents are selected from alkyl, hydroxy or alkoxy or, if attached to adjacent carbon atoms any two substituents together with the carbon atoms to which they are attached may form a fused heterocyclic ring of five to six atoms wherein one, two or three of the said atoms are oxygen or nitrogen; A represents a C 1-4 n-alkylene group wherein each carbon is optionally substituted by 1 or 2 C 1-6 alkyl groups; R 1 represents hydrogen, alkyl, alkenyl or cycloalkyl; one or two of of the group of R 2 , R 3 and R 4 represents nitro the remaining members of the group of R 2 , R 3 and R 4 represent hydrogen; X represents a —CO—NH— moiety; and Z represents C 2-4 n-alkylene group wherein each carbon is optionally substituted 1 or 2 C 1-6 alkyl groups; a process for preparing such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  化合物的化学式(I)：或其盐，或其溶剂化物，其中Ar代表取代或未取代的芳基，其中可选的取代基选自烷基，羟基或烷氧基，或者如果附加在相邻的碳原子上，则任意两个取代基与它们所附加的碳原子一起可以形成五至六个原子的融合杂环环，其中一，两个或三个所述原子为氧或氮; A代表C1-4n-烷基，其中每个碳原子可选择被1或2个C1-6烷基取代; R1代表氢，烷基，烯基或环烷基; R2，R3和R4组中的一或两个代表硝基，该组的其余成员代表氢; X代表—CO—NH—基团; Z代表C2-4n-烷基，其中每个碳原子可选择被1或2个C1-6烷基取代; 一种制备这种化合物的方法，包括这种化合物的制药组合物以及在医学上使用这种化合物的用途。
• NITRO-BENZAMIDES USEFUL AS ANTI-ARRHYTHMIC AGENTS
  申请人：SMITHKLINE BEECHAM LABORATOIRES PHARMACEUTIQUES

  公开号：EP0788474A1

  公开（公告）日：1997-08-13