N-(2-(3,4-二甲氧基苯基)乙基)-2-次氮基乙酰胺 | 98841-65-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-(3,4-二甲氧基苯基)乙基)-2-次氮基乙酰胺
• 中文别名: 2-氰基-N-[2-(3,4-二甲氧苯基)乙基]乙酰胺
• 英文名称: 2-cyano-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
• 英文别名: cyanoacetic acid homoveratrylamide；cyano-acetic acid-(3,4-dimethoxy-phenethylamide)；N-(3.4-Dimethoxy-phenaethyl)-C-cyan-acetamid；Malonsaeure-(3.4-dimethoxy-phenaethylamid)-nitril；Cyan-essigsaeure-(3,4-dimethoxy-phenaethylamid)；2-cyano-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide
• CAS: 98841-65-7
• 化学式: C₁₃H₁₆N₂O₃
• mdl: MFCD00170181
• 分子量: 248.282
• InChiKey: NMUPQXBMCWDTSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  N-(2-(3,4-二甲氧基苯基)乙基)-2-次氮基乙酰胺 在 四磷十氧化物 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 2-(3,4-dimethoxyphenyl)-3-methyl-8,9-dimethoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carbonitrile
  参考文献：
  名称：

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions

  摘要：

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and beta-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides.

  DOI：

  10.1134/s1070428011050137
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 、 氰乙酸乙酯 在 乙醇 作用下， 反应 15.0h， 以9.44 g (38.0 mmol, 60%) of 2-cyano-N-[2-(3,4-dimethoxy-phenyl)ethyl]-acetamide are obtained as a beige solid的产率得到N-(2-(3,4-二甲氧基苯基)乙基)-2-次氮基乙酰胺
  参考文献：
  名称：

  Pyrrolo-dihydroisoquinoline derivatives as pde10 inhibitors

  摘要：

  本发明涉及将吡咯并[2,1-a]异喹啉结构元素作为化合物整体结构的重要部分，以抑制PDE10的使用。

  公开号：

  US20070105840A1

文献信息

• [EN] NOVEL ARGINASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS D'ARGINASE
  申请人：UNIV GRONINGEN

  公开号：WO2020249821A1

  公开（公告）日：2020-12-17

  The present invention relates to novel arginase inhibitors of formula (I). These novel compounds are useful in the treatment of diseases that are associated with arginase activity, such as asthma, allergic rhinitis and COPD (chronic obstructive pulmonary disease).

  本发明涉及式(I)的新型精氨酸酶抑制剂。这些新型化合物在治疗与精氨酸酶活性相关的疾病方面具有用途，如哮喘、过敏性鼻炎和慢性阻塞性肺疾病（COPD）。
• Synthesis of N-Substituted γ-Methylene γ-Lactams
  作者：Raju Adhikari、Dionne A. Jones、Andris J. Liepa、Roland H. Nearn

  DOI：10.1071/ch05286

  日期：——

  N-Substituted cyanoacetamides 1 were condensed with 1,2-diketones 2 under base catalysis to form γ-hydroxy γ-lactams 3. Treatment of 3 with acids gave novel fungicidal γ-methylene γ-lactams 4. The exocyclic double bond of 4b reacted reversibly with 4-toluene sulfinate.

  在碱催化下，N-取代氰基乙酰胺 1 与 1,2-二酮 2 缩合生成γ-羟基γ-内酰胺 3。用酸处理 3 可以得到新型杀菌的γ-亚甲基γ-内酰胺 4。4b 的外环双键与 4-甲苯亚磺酸盐发生了可逆反应。
• [EN] PYRROLODIHYDROISOQUINOLINES AS PDE10 INHIBITORS<br/>[FR] PYRROLODIHYDROISOQUINOLINES COMME INHIBITEURS DE PDE10
  申请人：ALTANA PHARMA AG

  公开号：WO2005003129A1

  公开（公告）日：2005-01-13

  The invention relates to novel pyrrolodihydroisoquinoline derivatives, which are efficacious inhibitors of PDE10.

  这项发明涉及新颖的吡咯二氢异喹啉衍生物，它们是有效的PDE10抑制剂。
• Pyrrolodihydroisoquinolines as pde10 inhibitors
  申请人：Vennemann Matthias

  公开号：US20060148840A1

  公开（公告）日：2006-07-06

  The invention relates to novel pyrrolodihydroisoquinoline derivatives, which are efficacious inhibitors of PDE10.

  本发明涉及新型吡咯二氢异喹啉衍生物，其是PDE10的有效抑制剂。
• Tyrphostins. II. Heterocyclic and .alpha.-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases
  作者：Aviv Gazit、Nir Osherov、Israel Posner、Pnina Yaish、Enrique Poradosu、Chaim Gilon、Alexander Levitzki

  DOI：10.1021/jm00110a022

  日期：1991.6

  We have previously described a novel series of low molecular weight protein tyrosine kinase inhibitors which we named tyrphostins. The characteristic active pharmacophore of these compounds was the hydroxy-cis-benzylidenemalononitrile moiety. In this article we describe three novel groups of tyrphostins: (i) one group has the phenolic moiety of the cis-benzylidenemalononitrile replaced either with other substituted benzenes or with heteroaromatic rings, (ii) another is a series of conformationally constrained derivatives of hydroxy-cis-benzylidenemalononitriles in which the malononitrile moiety is fixed relative to the aromatic ring, and (iii) two groups of compounds in which the position trans to the benzenemalononitrile has been substituted by ketones and amides. Among the novel tyrphostins examined we found inhibitors which discriminate between the highly homologous EGF receptor kinase (HER1) and ErbB2/neu kinase (HER2). These findings may lead to selective tyrosine kinase blockers for the treatment of diseases in which ErbB2/neu is involved.