3-[N-(3,4-dimethoxyphenyl)ethyl-N-methylamino]propylamine | 55982-99-5

• 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: 3-[N-(3,4-dimethoxyphenyl)ethyl-N-methylamino]propylamine
• 英文别名: N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methyl-1,3-propanediamine；N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylpropane-1,3-diamine；1-[N-methyl-N-(2(3,4-dimethoxy-phenyl)-ethyl)-amino]-3-aminopropane；N-methyl-N-(2-(3,4-dimethoxyphenyl)ethyl)-1,3-diaminopropane；1-[N-methyl-2-(3,4-dimethoxyphenyl)-ethylamino]-3-amino-propane；1-[2-(3,4-dimethoxy-phenyl)-ethyl-methylamino]-3-amino-propane；N-[2-(3,4-dimethoxyphenyl)-ethyl]-N-methyl-1,3-propanediamine；N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-1,3-propanediamine；1,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-；N'-[2-(3,4-dimethoxyphenyl)ethyl]-N'-methylpropane-1,3-diamine
• CAS: 55982-99-5
• 化学式: C₁₄H₂₄N₂O₂
• 分子量: 252.357
• InChiKey: JWANNLXCVGJLAS-UHFFFAOYSA-N

物化性质

• 沸点：
  366.1±37.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[N-(3,4-dimethoxyphenyl)ethyl-N-methylamino]propylamine 在 溶剂黄146 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 生成 法利帕米
  参考文献：
  名称：

  特定的缓动剂。1.取代的苯并ze庚因酮的化学，药理学和结构-活性关系，这是一类具有抗缺血特性的新型化合物。

  摘要：

  通过用各种杂环系统取代亲脂性α-异丙基乙腈部分对钙拮抗剂维拉帕米（1）进行结构修饰，导致了一类新型的心血管化合物，其特点是具有特定的缓动心律活动。这些药物可降低心律，而不会结合经典的钙通道或β-肾上腺素受体，而是与窦房结的结构发生特异性相互作用。因此，它们也被称为窦房结抑制剂。原型法利帕米（2）已通过进一步处理邻苯二甲moiety部分进行了进一步优化。这导致了第二代特定的缓动性药物，这些药物具有增强的功效，并以苯并ze庚因衍生物UL-FS 49（4）为代表，选择性地延长了作用时间。这类新型化合物中的结构活性关系揭示了活性对芳环的取代方式，中心氮原子的性质以及连接的烷基链长度的显着依赖性。苯并ze庚酮环对缓动性活动的关键作用可以通过其对整体分子构象的特殊影响来最好地解释。

  DOI：

  10.1021/jm00167a033
• 作为产物：
  描述：

  <<2-(3,4-dimethoxyphenyl)ethyl>methylamino>propanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-[N-(3,4-dimethoxyphenyl)ethyl-N-methylamino]propylamine
  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

• Butenoic or propenoic acid derivatives
  申请人：Eisai Co. Ltd.

  公开号：US05047417A1

  公开（公告）日：1991-09-10

  A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydrogen or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field. ##STR1##

  一种具有以下结构式的丁烯酸或丙烯酸衍生物，其中G是芳基或杂环环，R11和R12是氢或烷基，X是硫或氧，R2和R3是氢，取代基如烷基，J是吡啶基或苯基，具有取代基和杂环环可能形成在R2、R3和J之间，该化合物在药学领域中具有用途。
• Quantitative Structure–Activity Analyses of Novel Hydroxyphenylurea Derivatives as Antioxidants
  作者：Kazuya Nakao、Ryo Shimizu、Hitoshi Kubota、Mikiko Yasuhara、Yoshimasa Hashimura、Toshikazu Suzuki、Toshio Fujita、Hiroshi Ohmizu

  DOI：10.1016/s0968-0896(98)00039-x

  日期：1998.6

  importance in governing the inhibitory potency. An increase in the electron donating property of substituents toward the phenolic hydroxyl group enhanced the antioxidative activity by the stabilization of an electron-deficient radical-type transition state. The steric shielding by ortho-substituents stabilized the phenoxy radicals formed following the transition state. Derivatives having the carboxyl group

  合成了一系列取代的羟基苯基脲，其化学结构是基于天然抗氧化剂，维生素E（α-生育酚）和尿酸的结构设计的。它们显示出对脂质过氧化的高抑制活性。为了深入了解抑制反应的机理，我们定量分析了它们的构效关系。取代基对酚羟基的电子和空间效应显示出对控制抑制效力的重要性。取代基对酚羟基的给电子性的增加通过稳定电子缺陷的自由基型过渡态而增强了抗氧化活性。邻位取代基的空间屏蔽作用稳定了过渡态后形成的苯氧基。推测具有羧基的衍生物仅是弱活性的，这是因为酚羟基与羧酸根阴离子的分子间离子-偶极相互作用会延迟过渡态的形成。
• Synthesis and Cardiovascular Activity of Phenylalkylamine Derivatives. I. Potential Specific Bradycardic Agents.
  作者：Fumihiro OZAKI、Masayuki MATSUKURA、Yasuhiro KABASAWA、Keiji ISHIBASHI、Megumi IKEMORI、Sachiyuki HAMANO、Norio MINAMI

  DOI：10.1248/cpb.40.2735

  日期：——

  A series of acyclic amide derivatives of N-(ω-aminoalkyl)-N-methylhomoveratrylamine was synthesized and evaluated for their bradycardic activity in isolated guinea pig right atria. Among these compounds, (E)-N-[3-[N'-2-(3, 4-dimethoxyphenyl)ethyl]-N'-methylamino]propyl]-4-[3, 4-(methylenedioxy)phenyl]-3-butenamide (35) was the most potent in vitro and was also found to show dose-dependent bradycardia without remarkable reduction of left ventricular dp/dtmax or mean aortic pressure in anesthetized dogs.

  合成了一系列N-(ω-氨基烷基)-N-甲基homoveratrylamine的非环状酰胺衍生物，并评估其在孤立豚鼠右心房中的减心率活性。在这些化合物中，(E)-N-[3-[N'-2-(3, 4-二甲氧基苯)乙基]-N'-甲基氨基]丙基]-4-[3, 4-(亚甲基二氧基)苯]-3-丁酰胺（35）在体外表现出最强的效力，并且在麻醉犬中还发现表现出剂量依赖性的减心率，而对左心室dp/dtmax或平均主动脉压力的显著降低并不明显。
• Nitro-benzamides useful as anti-arrhythmic agents
  申请人：SmithKline Beecham p.l.c.

  公开号：US05977179A1

  公开（公告）日：1999-11-02

  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.sub.1-4 n-alkylene group wherein each carbon is optionally substituted by 1 or 2 C.sub.1-6 -alkyl groups; R.sub.1 represents hydrogen, alkyl, alkenyl or cycloalkyl; one or two of the group of R.sub.2, R.sub.3 and R.sub.4 represents nitro the remaining members of the group of R.sub.2, R.sub.3 and R.sub.4 represent hydrogen; X represents a --CO--NH-- moiety; and Z represents C.sub.2-4 n-alkylene group wherein each carbon is optionally substituted 1 or 2 C.sub.1-6 alkyl groups; a process for preparing such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  公式（I）的化合物，或其盐，或其溶剂化合物，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，或如果连接到相邻的碳原子，则任意两个取代基与它们连接的碳原子一起可以形成含有五到六个原子的融合杂环环，其中所述原子中的一个、两个或三个是氧或氮；A代表C.sub.1-4 n-烷基烯基，其中每个碳原子可选择地被1或2个C.sub.1-6-烷基基团取代；R.sub.1代表氢，烷基，烯基或环烷基；R.sub.2，R.sub.3和R.sub.4中的一个或两个代表硝基，R.sub.2，R.sub.3和R.sub.4的其余成员代表氢；X代表--CO--NH--基团；Z代表C.sub.2-4 n-烷基基团，其中每个碳原子可选择地被1或2个C.sub.1-6烷基基团取代；制备这种化合物的方法，包括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。
• 1,3-Dioxo-2-aminoalkyl-4,4-dimethyl-isoquinolines and salts thereof
  申请人：Boehringer Ingelheim GmbH

  公开号：US03948898A1

  公开（公告）日：1976-04-06

  Compounds of the formula ##SPC1## Wherein R.sub.1 is hydrogen, halogen, methoxy or methylthio R.sub.2 is hydrogen or methoxy, n is 2 or 3, and A is ##SPC2## Or ##SPC3## Where R.sub.3 is hydrogen or methyl, R.sub.4 is pyridyl, methy-pyridyl, phenyl, chlorophenyl, trifluoromethyl-phenyl, tolyl, xylyl, ethyl-phenyl, diethyl-phenyl, methoxy-phenyl or dimethoxy-phenyl, and R.sub.5 and R.sub.6, which may be identical to or different from each other, are each hydrogen or methoxy, And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as the salts are useful as hypotensives, sedatives, antiarrhythmics and bradycardiacs.

  式##SPC1##的化合物，其中R.sub.1是氢、卤素、甲氧基或甲硫基，R.sub.2是氢或甲氧基，n为2或3，A为##SPC2##或##SPC3##其中R.sub.3为氢或甲基，R.sub.4为吡啶基、甲基吡啶基、苯基、氯苯基、三氟甲基苯基、甲苯基、二甲苯基、乙基苯基、二乙基苯基、甲氧基苯基或二甲氧基苯基，R.sub.5和R.sub.6可相同也可不同，均为氢或甲氧基，以及其非毒性、药理学上可接受的酸盐；这些化合物及其盐可用作降压药、镇静剂、抗心律失常药和缓慢心率药。