N-(2,3-dimethoxybenzyl)aminoacetaldehyde diethyl acetal | 53762-16-6

• 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-dimethoxybenzyl)aminoacetaldehyde diethyl acetal
• 英文别名: dimethoxy-2,3 benzylaminoacetal diethylique；(2,2-diethoxy-ethyl)-(2,3-dimethoxy-benzyl)-amine；(2,3-dimethoxy-benzylamino)-acetaldehyde diethyl acetal；N-(2,3-dimethoxybenzyl)-2,2-diethoxyethanamine；N-[(2,3-dimethoxyphenyl)methyl]-2,2-diethoxyethanamine
• CAS: 53762-16-6
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: BCQDFNHNUDHENS-UHFFFAOYSA-N

物化性质

• 沸点：
  352.3±37.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2,3-dimethoxybenzyl)aminoacetaldehyde diethyl acetal 在 镍 盐酸 、 氢气 、 铬酸 作用下， 以 甲醇 、 水 为溶剂， 25.0 ℃ 、200.0 kPa 条件下， 反应 21.5h， 生成 dimethoxy-7,8 methyl-2 trioxo-1,3,4 tetrahydroisoquinoleine
  参考文献：
  名称：

  Leseche, Bernard; Gilbert, Jacques; Viel, Claude, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 143 - 153

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二乙氧基乙酰胺 在 镍 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 生成 N-(2,3-dimethoxybenzyl)aminoacetaldehyde diethyl acetal
  参考文献：
  名称：

  Bouvier,P. et al., European Journal of Medicinal Chemistry, 1976, vol. 11, p. 271 - 278

  摘要：

  DOI：
• 作为试剂：
  描述：

  (E)-N-(2,2-diethoxy-ethyl)-(2,3-dimethoxy-benzylidene)-amine 、 硼氢化钠 在 氮 、 氯仿 、 水 、 Brine 、 magnesium sulfate 、 N-(2,3-dimethoxybenzyl)aminoacetaldehyde diethyl acetal 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以to give N-(2,3-dimethoxybenzyl)-2,2-diethoxyethanamine LPO 26048 as a yellow oil (14.1 g, 85% crude yield)的产率得到N-(2,3-dimethoxybenzyl)aminoacetaldehyde diethyl acetal
  参考文献：
  名称：

  SUBSTITUTED ISOQUINOLINES AND THEIR USE AS TUBULIN POLYMERIZATION INHIBITORS

  摘要：

  本发明涉及替代异喹啉及其作为微管聚合抑制剂的用途。具体而言，本发明涉及具有有用治疗活性的替代异喹啉，这些化合物在治疗方法中的使用以及制药和含有这些化合物的组合物的制造。

  公开号：

  US20130131018A1

文献信息

• [EN] SUBSTITUTED ISOQUINOLINES AND THEIR USE AS TUBULIN POLYMERIZATION INHIBITORS<br/>[FR] ISOQUINOLÉINES SUBSTITUÉES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE POLYMÉRISATION DES TUBULINES
  申请人：EXONHIT S A

  公开号：WO2011151423A1

  公开（公告）日：2011-12-08

  The present invention relates generally to substituted isoquinolines and their use as tubulin polymerization inhibitors. In particular, the invention relates to substituted isoquinolines which possess useful therapeutic activity, use of these compounds in methods of therapy and the manufacture of medicaments as well as compositions containing these compounds.

  本发明总体上涉及取代异喹啉及其作为微管蛋白聚合抑制剂的应用。特别是，本发明涉及具有有用的治疗活性的取代异喹啉，这些化合物在治疗方法、药物制造以及含有这些化合物的组合物中的应用。
• 4-(3,4-Dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline Derivatives. II. Their Renal Vasodilation Activity and Structure-Activity Relationship.
  作者：Hideki ANAN、Akihiro TANAKA、Ryuji TSUZUKI、Masaki YOKOTA、Takeyuki YATSU、Takashi FUJIKURA

  DOI：10.1248/cpb.44.1865

  日期：——

  A series of 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline derivatives showed potent DA1 agonistic activities. We investigated the structure-activity relationship of the racemic compounds of this series. 4-(3,4-Dihydroxyphenyl)-7-methanesulfonamido-1,2,3,4-tetrahydroiso quinoline (43) was identified as a potent renal vasodilator with activity almost equal to that of YM435 (1).

  一系列的4-（3,4-二羟基苯基）-1,2,3,4-四氢异喹啉衍生物显示出强大的DA1激动活性。我们研究了该系列外消旋化合物的构效关系。4-（3,4-二羟基苯基）-7-甲磺酰胺基-1,2,3,4-四氢异喹啉（43）被确定为有效的肾血管扩张药，其活性几乎与YM435（1）相等。
• Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[<i>c,f</i>]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure
  作者：Agnieszka Grajewska、Maria Chrzanowska、Wiktoria Adamska

  DOI：10.3762/bjoc.17.168

  日期：——

  A convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted benzyl groups as the amine components followed by Pomeranz–Fritsch double cyclization reaction. By applying

  开发了一种方便、简单的方案，通过三组分 Petasis 反应合成一系列新型四环四氢异喹啉衍生物 7,12-二氢-6,12-亚甲基二苯并[ c,f ]-偶氮辛-5-羧酸。使用带有取代苄基的氨基乙醛缩醛作为胺组分，然后进行 Pomeranz-Fritsch 双环化反应。通过应用该方法，已经以令人满意的收率制备了几种酸。观察到 Petasis 反应产物在稀 HCl 溶液中形成苯基甘氨酸衍生物的前所未有的化学行为，并提出了解释这种反应性的机制。
• REVERSE-TURN MIMETICS AND METHOD RELATING THERETO
  申请人：Moon Sung Hwan

  公开号：US20100222303A1

  公开（公告）日：2010-09-02

  Conformationally constrained compounds that mimic the secondary structure of reverse-turn regions of biologically active peptides and proteins as well as their prodrugs are disclosed. Such reverse-turn mimetic structures and prodrugs have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the reverse-turn mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members. The invention also relates to the use of such compounds and prodrugs for inhibiting or treating disorders modulated by Wnt-signaling pathway, such as cancer, especially colorectal cancer, restenosis associated with angioplasty, polycystic kidney disease, aberrant angiogenesis disease, rheumatoid arthritis disease, tuberous sclerosis complex, Alzheimer's disease, excess hair growth or loss, or ulcerative colitis.

  本发明揭示了限制构象的化合物，其模拟生物活性肽和蛋白质的反转区域的二级结构以及它们的前药。这种反转区域模拟结构和前药在广泛的领域中具有实用性，包括用作诊断和治疗剂。本发明还揭示了包含这种反转区域模拟结构的库以及筛选相同以识别生物活性成员的方法。本发明还涉及使用这种化合物和前药来抑制或治疗由Wnt信号通路调节的疾病，例如癌症，特别是结肠直肠癌，与血管成形术相关的再狭窄，多囊肾病，异常血管生成疾病，类风湿性关节炎疾病，结节性硬化症，阿尔茨海默病，过度生长或脱发，或溃疡性结肠炎。
• Reverse-turn mimetics and method relating thereto
  申请人：Choongwae Pharma Corporation

  公开号：US08138337B2

  公开（公告）日：2012-03-20

  Conformationally constrained compounds that mimic the secondary structure of reverse-turn regions of biologically active peptides and proteins as well as their prodrugs are disclosed. Such reverse-turn mimetic structures and prodrugs have utility over a wide range of fields, including use as diagnostic and therapeutic agents. Libraries containing the reverse-turn mimetic structures of this invention are also disclosed as well as methods for screening the same to identify biologically active members. The invention also relates to the use of such compounds and prodrugs for inhibiting or treating disorders modulated by Wnt-signaling pathway, such as cancer, especially colorectal cancer, restenosis associated with angioplasty, polycystic kidney disease, aberrant angiogenesis disease, rheumatoid arthritis disease, tuberous sclerosis complex, Alzheimer's disease, excess hair growth or loss, or ulcerative colitis.

  本发明揭示了构象受限化合物，其模拟生物活性肽和蛋白质的反转区域的二级结构，以及它们的前药。这样的反转区模拟结构和前药在广泛的领域中具有实用性，包括用作诊断和治疗剂。本发明还揭示了包含这些反转区模拟结构的库，以及筛选这些库以识别生物活性成员的方法。本发明还涉及使用这样的化合物和前药来抑制或治疗由Wnt信号通路调节的疾病，如癌症，特别是结肠直肠癌，与血管成形术相关的再狭窄，多囊肾病，异常血管生成疾病，类风湿性关节炎疾病，结节性硬化症，阿尔茨海默病，过度毛发生长或脱发，或溃疡性结肠炎。