N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methyl-1,4-butanediamine | 127404-85-7

• 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-<2-(3,4-dimethoxyphenyl)ethyl>-N-methyl-1,4-butanediamine
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylbutane-1,4-diamine；N1-(3,4-dimethoxyphenethyl)-N1-methylbutane-1,4-diamine；N'-[2-(3,4-dimethoxyphenyl)ethyl]-N'-methylbutane-1,4-diamine
• CAS: 127404-85-7
• 化学式: C₁₅H₂₆N₂O₂
• 分子量: 266.384
• InChiKey: VLEXWFDTROSNQA-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±37.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methyl-1,4-butanediamine 在 Dowex 1X₈ chloride resin 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成 Quinoline-3-carboxylic acid [2-(4-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-butylcarbamoyl)-phenyl]-amide
  参考文献：
  名称：

  In vitro activity of novel dual action MDR anthranilamide modulators with inhibitory activity at CYP-450

  摘要：

  Synthesis and in vitro cytotoxicity assays of new anthranilamide MDR modulators have been performed to assess their inhibition potency of the P-glycoprotein (P-gp) transporter. The aromatic spacer group between nitrogen atoms (N1 and N2) in the known inhibitor XR9576 was replaced with a flexible alkyl chain of 2 to 6 carbon atoms in length. 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline and their open-chain N-methylhomoveratrylamine counterparts were shown to be potent P-gp inhibitors. The maximal inhibition was obtained when using an ethyl or propyl spacer. Several compounds were more potent than verapamil and intrinsically less cytotoxic than XR9576. In addition, in vitro metabolism studies of 23a with a subset of human CYP-450 isoforms revealed that, unlike XR9576, 23a inhibited CYP3A4, an enzyme that colocalizes with P-gp in the intestine and contributes to tumor cell chemoresistance by enhancing the biodisposition of anticancer drugs such as paclitaxel toward metabolism. In this context, 22a might be a suitable candidate for further drug development.

  DOI：

  10.1016/j.bmc.2006.07.055
• 作为产物：
  描述：

  N-(3,4-dimethoxyphenethyl)-N-(3-cyanopropyl)formamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methyl-1,4-butanediamine
  参考文献：
  名称：

  Effect of structural modification in the amine portion of substituted aminobutyl-benzamides as ligands for binding σ1 and σ2 receptors

  摘要：

  5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl)]-2,3-dimethoxy-benzamide (1) is one of the most potent and selective sigma(2) receptor ligands reported to date. A series of new analogs, where the amine ring fused to the aromatic ring was varied in size (5-7) and the location of the nitrogen in this ring was modified, has been synthesized and assessed for their sigma(1)/sigma(2) binding affinity and selectivity. The binding affinity of an open-chained variant of 1 was also evaluated. Only the five-membered ring congener of 1 displayed a higher sigma(1)/sigma(2) selectivity, derived from a higher sigma(2) affinity and a lower sigma(1) affinity. Positioning the nitrogen adjacent to the aromatic ring in the five-membered and six-membered ring congeners dramatically decreased affinity for both subtypes. Thus, location of the nitrogen within a constrained ring is confirmed to be key to the exceptional sigma(2) receptor binding affinity and selectivity for this active series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.006

文献信息

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

  公开号：EP0344577A2

  公开（公告）日：1989-12-06

  A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben 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.

  丁烯酸或丙烯酸衍生物具有下式，其中 G 为芳基或杂环，R11 和 R12 为氢基或烷基，X 为硫或氧，R2 和 R3 为氢，取代基如烷基，J 为吡啶基或苯基，R2、R3 和 J 之间可形成杂环，该衍生物在药理学领域非常有用。
• Butenoic acid derivatives
  申请人：Eisai Co., Ltd.

  公开号：EP0399358A2

  公开（公告）日：1990-11-28

  A butenoic acid compound is defined by the following formula: in which Z is O,S, vinylene or azomethyne, A is an alkylene and J is phenyl or etc. It is useful to treat the heart disease.

  丁烯酸化合物由下式定义： 其中 Z 为 O、S、乙烯基或偶氮甲基，A 为亚烷基，J 为苯基或其他。它可用于治疗心脏病。
• US5047417A
  申请人：——

  公开号：US5047417A

  公开（公告）日：1991-09-10
• US5177089A
  申请人：——

  公开号：US5177089A

  公开（公告）日：1993-01-05