N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-ethane-1,2-diamine | 63005-32-3

• 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-ethane-1,2-diamine
• 英文别名: 2-[[N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylamino]]ethyl-amine；N'-[2-(3,4-dimethoxyphenyl)ethyl]-N'-methylethane-1,2-diamine
• CAS: 63005-32-3
• 化学式: C₁₃H₂₂N₂O₂
• mdl: MFCD19323500
• 分子量: 238.33
• InChiKey: RCYQJSASQWXACC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 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-ethane-1,2-diamine 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-(2-{[2-(3,4-dimethoxy-phenyl)-ethyl]-methyl-amino}-ethylcarbamoyl)-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：

  (3,4-二甲氧基苯乙基)(甲基)铵碘化物 在 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis and Cardiovascular Activity of Phenylalkylamine Derivatives. I. Potential Specific Bradycardic Agents.

  摘要：

  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。

  DOI：

  10.1248/cpb.40.2735

文献信息

• Studies on the chemistry of thienoannelated<i>O,N</i>- and<i>S,N</i>-containing heterocycles. 17. Preparation of 1<i>H</i>-thieno[2,3-b][1,4]thiazine-1-carboxarnides as smooth muscle relaxants
  作者：Maria E. Schreder、Thomas Erker

  DOI：10.1002/jhet.5570370220

  日期：2000.3

  A new series of substituted thieno[1,4]thiazines with an urea moiety has been designed. The synthesis and results of replacement of the quinoline and indoline moieties of lead structure 1 are described. The key step in preparation was the substitution with 4-nitrophenyl chloroformate to obtain the required reactivity for substitution with diamines. Structural modifications of the amino side chain with

  设计了一系列新的具有脲部分的取代噻吩并[1,4]噻嗪。描述了引线结构1的喹啉和吲哚部分的合成和取代结果。制备的关键步骤是用氯甲酸4-硝基苯酯取代以获得所需的反应性，以二胺取代。为了发现组织特异性化合物，进行了氨基侧链的结构修饰。药理测试探索了推测的钙通道拮抗作用和钾通道开放作用。
• Zur Synthese von ionenkanalblockierenden Substanzen mit Thieno[2,3-b][1,4]thiazin-, 1,4-Benzoxazin und 1,4-Benzothiazin-Grundgerüst
  作者：M. E. Schreder、T. Erker

  DOI：10.3797/scipharm.aut-00-07

  日期：——

  The syntheses of the thieno[2,3-b)[1,4]thiazine derivatives 8 and 9 are described. Reaction of compound 4 with different acyl halides followed by substitution with various ethanamines gave the products 8 and 9. The new 3,4-dihydro-2H-1,4-benzoxazine derivatives 14, 16, 18 and 3,4-dihydro-2H-1,4-benzothiazine derivatives 15 and 17 with an urea moiety have been synthesized. Substitution of 10 respectively

  描述了噻吩并[2,3-b] [1,4]噻嗪衍生物8和9的合成。化合物4与不同的酰基卤反应，然后用各种乙醇胺取代，得到产物8和9。新的3,4-二氢-2H-1,4-苯并恶嗪衍生物14、16、18和3,4-二氢-2H已经合成了具有脲部分的-1，4-苯并噻嗪衍生物15和17。用氯甲酸4-硝基苯酯分别取代10和11，得到所需的被二胺取代的反应性。进行了氨基侧链的结构修饰。
• 2-Phenylalkyl-3-aminoalkyl-4(3H)-quinazolinone compound
  申请人：Mitsubishi Chemical Industries Limited

  公开号：US04668682A1

  公开（公告）日：1987-05-26

  Disclosed are a 2-phenylalkyl-3-aminoalkyl-4(3H)-quinazolinone compound of Formula (1): ##STR1## wherein, X represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a phenoxy group, a benzyloxy group, a halogen atom or a hydroxy group; Y represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a benzyloxy group, a halogen atom or a nitro group; R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; R.sup.2 represents an alkyl group having 1 to 5 carbon atoms or a group of Formula (2) ##STR2## [wherein, Z represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogen atom; d is an integer of 1 to 3; and l is an integer of 1 to 5]; or R.sup.1 and R.sup.2 represent together with the nitrogen atom to which they are attached, a cyclic amino group of the formula: ##STR3## [wherein, A represents an alkylene group having 2 to 6 carbon atoms or a group of the formula --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --]; a and b are independently an integer of 1 to 3; and n and m are independently an integer of 1 to 5, or a pharmaceutically acceptable acid addition salt thereof, a process for preparing said compound, a composition comprising said compound as an active ingredient and a method of treatment by use of said compound. The compounds of the present invention have calcium antagonistic, vasodilative, and antihypertensive activities.

  本发明公开了一种具有以下结构的2-苯基烷基-3-氨基烷基-4(3H)-喹唑啉酮化合物（式中，X代表氢原子、具有1到5个碳原子的烷基基团、具有1到5个碳原子的烷氧基团、苯氧基团、苄氧基团、卤素原子或羟基；Y代表具有1到5个碳原子的烷基基团、具有1到5个碳原子的烷氧基团、苄氧基团、卤素原子或硝基基团；R.sup.1代表氢原子或具有1到5个碳原子的烷基基团；R.sup.2代表具有1到5个碳原子的烷基基团或式(2)的基团[式中，Z代表氢原子、具有1到5个碳原子的烷基基团、具有1到5个碳原子的烷氧基团或卤素原子；d为1到3的整数；l为1到5的整数]；或R.sup.1和R.sup.2与它们连接的氮原子一起代表下述结构的环氨基基团：[式中，A代表具有2到6个碳原子的烷基基团或式--(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --]；a和b独立地为1到3的整数；n和m独立地为1到5的整数；或其药学上可接受的酸盐，制备该化合物的方法，含有该化合物作为活性成分的组合物以及使用该化合物进行治疗的方法。本发明的化合物具有钙拮抗、扩血管和降压活性。
• 2-Phenylalkyl-3-aminoalkyl-4(3H)-quinazolinones, processes for preparing them, pharmaceutical compositions and use
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0169537A2

  公开（公告）日：1986-01-29

  Disclosed are a 2-phenylalkyl-3-aminoalkyl-4(3H)-quinazolinone compound of Formula (1): werein, X represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a phenoxy group, a benzyloxy group, a halogen atom or a hydroxy group; Y represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a benzyloxy group, a halogen atom or a nitro group: R' represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; R2 represents an alkyl group having 1 to 5 carbon atoms or a group of Formula (2) [wherein, Z represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom; is an integer of 1 to 3; and l is an integer of 1 to 5]; or R1 and R2 represent together with the nitrogen atom to which they are attached, a cyclic amino group of the formula: [wherein, A represents an alkylene group having 2 to 6 carbon atoms or a group of the formula -(CH2)2-O-(CH2)2-]; a and b are independently an integer of 1 to 3; and n and m are independently an integer of 1 to 5, or a pharmaceutically acceptable acid addition salt thereof, a process for preparing said compound, a composition comprising said compound as an active ingredient and a use of the said compound for the preparing of a pharmaceutical composition. The compounds of the present invention have calcium antagonistic, vasodilative, and antihypertensive activities.

  本发明公开了一种式（1）的 2-苯基烷基-3-氨基烷基-4(3H)-喹唑啉酮化合物： 其中，X 代表氢原子、具有 1 至 5 个碳原子的烷基、具有 1 至 5 个碳原子的烷氧基、苯氧基、苄氧基、卤素原子或羟基；Y 代表具有 1 至 5 个碳原子的烷基、具有 1 至 5 个碳原子的烷氧基、苯氧基、苄氧基、卤素原子或羟基。 代表 1 至 5 个碳原子的烷基、1 至 5 个碳原子的烷氧基、苄氧基、卤素原子或硝基：R' 代表氢原子或具有 1 至 5 个碳原子的烷基； R2 代表具有 1 至 5 个碳原子的烷基或式（2）的基团 [其中，Z 代表氢原子、具有 1 至 5 个碳原子的烷基、具有 1 至 5 个碳原子的烷氧基或卤素原子；是 1 至 3 的整数；l 是 1 至 5 的整数]；或 R1 和 R2 与它们所连接的氮原子一起代表式（2）的环状氨基： [其中，A 代表具有 2 至 6 个碳原子的亚烷基或式-(CH2)2-O-(CH2)2-]的基团；a 和 b 独立地为 1 至 3 的整数；n 和 m 独立地为 1 至 5 的整数，或其药学上可接受的酸加成盐，制备所述化合物的工艺，包含所述化合物作为活性成分的组合物，以及所述化合物用于制备药物组合物的用途。 本发明的化合物具有钙拮抗、血管扩张和降压活性。
• 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。