2-[(2,2-二甲氧基乙基)氨基]-N-(2-苯基乙基)乙酰胺盐酸盐 | 210223-97-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-[(2,2-二甲氧基乙基)氨基]-N-(2-苯基乙基)乙酰胺盐酸盐
• 英文名称: 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide hydrochloride
• 英文别名: 2-(2,2-dimethoxy ethylamino)-N-phenethyl-acetamide hydrochloride；2-(2,2-Dimethoxy-ethylamino)-N-phenethyl-acetamide hydrochloride；2-(2,2-dimethoxyethylamino)-N-(2-phenylethyl)acetamide;hydrochloride
• CAS: 210223-97-5
• 化学式: C₁₄H₂₂N₂O₃*ClH
• 分子量: 302.801
• InChiKey: NVPWYOJPRJWWJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.47
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2,2-二甲氧基乙基)氨基]-N-(2-苯基乙基)乙酰胺盐酸盐 在 硫酸 、 D-二苯甲酰酒石酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 7.5h， 生成 (S)-praziquanamine
  参考文献：
  名称：

  One-Pot Palladium-Catalyzed Racemization of (S)-Praziquanamine: A Key Intermediate for the Anthelmintic Agent (R)-Praziquantel

  摘要：

  An one-pot palladium-catalyzed procedure for racemization of (S)-praziquanamine, which is the undesired enantiomer and produced during the resolution step for preparing the anthelmintic drug (R)-praziquantel, has been developed through dehydrogenation of (S)-praziquanamine into 6,7-dihydro-4H-pyrazino[2,1-a]isoquinolin-4-one and then hydrogenation of the double bonds. And a superior racemization method was also developed that (S)-praziquanamine was directly treated with Pd/C under H-2 atmosphere to obtain a racemic mixture in quantitative yield with 95% chemical purity. Such a concise and efficient approach to the racemization of (S)-praziquanamine can be useful to recycle the waste enantiomer into the resolution process to obtain the (R)-enantiomer on a large scale.

  DOI：

  10.3987/com-16-13606
• 作为产物：
  描述：

  2-苯乙胺 在 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 2-[(2,2-二甲氧基乙基)氨基]-N-(2-苯基乙基)乙酰胺盐酸盐
  参考文献：
  名称：

  One-Pot Palladium-Catalyzed Racemization of (S)-Praziquanamine: A Key Intermediate for the Anthelmintic Agent (R)-Praziquantel

  摘要：

  An one-pot palladium-catalyzed procedure for racemization of (S)-praziquanamine, which is the undesired enantiomer and produced during the resolution step for preparing the anthelmintic drug (R)-praziquantel, has been developed through dehydrogenation of (S)-praziquanamine into 6,7-dihydro-4H-pyrazino[2,1-a]isoquinolin-4-one and then hydrogenation of the double bonds. And a superior racemization method was also developed that (S)-praziquanamine was directly treated with Pd/C under H-2 atmosphere to obtain a racemic mixture in quantitative yield with 95% chemical purity. Such a concise and efficient approach to the racemization of (S)-praziquanamine can be useful to recycle the waste enantiomer into the resolution process to obtain the (R)-enantiomer on a large scale.

  DOI：

  10.3987/com-16-13606

文献信息

• Synthesis of “Trioxaquantel”® Derivatives as Potential New Antischistosomal Drugs
  作者：Sophie A.-L. Laurent、Jérôme Boissier、Frédéric Coslédan、Heinz Gornitzka、Anne Robert、Bernard Meunier

  DOI：10.1002/ejoc.200700975

  日期：2008.2

  complementarity of the two drug classes – praziquantel and artemisinin deriv-atives – we designed new molecules, named trioxaquantels®, that combine the 1,2,4-trioxane unit responsible for the activity of artemisinin, and the pyrazinoisoquinoline moiety of praziquantel within a single drug. The synthesis of these new drugs and their preliminary evaluation in mice infected with Schistosoma mansoni is reported

  在过去的 20 年中，吡喹酮，一种吡嗪基异喹啉衍生物，已成为控制人和动物血吸虫病发病率的中流砥柱。从脊椎动物宿主的生命早期开始，血吸虫吸收血红蛋白并将释放的血红素聚集为一种黑色色素，与疟疾感染中疟原虫产生的血红素非常相似。抗疟药青蒿素衍生物具有真实但低的杀血吸虫活性。由于吡喹酮和青蒿素衍生物这两个药物类别的互补性，我们设计了名为 trioxaquantels® 的新分子，它结合了负责青蒿素活性的 1,2,4-三恶烷单元和吡喹酮的吡嗪异喹啉部分在单一药物内。
• Design and Synthesis of Novel Pyrazino[2,1-a]isoquinolin Derivatives with Potent Antifungal Activity
  作者：Hui Tang、Can-hui Zheng、Ju Zhu、Bing-yue Fu、You-jun Zhou、Jia-guo Lv

  DOI：10.1002/ardp.200900279

  日期：——

  A series of novel pyrazino[2,1‐a]isoquinolin compounds were designed, synthesized, and their antifungal activities in vitro were evaluated. The results showed that all of the title compounds exhibited antifungal activities. Most of them exhibited stronger antifungal activities than the lead compounds; compound 7c is more potent than fluconazole against two of the three tested fungal strains. The studies

  设计、合成了一系列新型吡嗪并 [2,1-a] 异喹啉化合物，并评估了它们的体外抗真菌活性。结果表明，所有标题化合物均表现出抗真菌活性。它们中的大多数表现出比先导化合物更强的抗真菌活性；化合物 7c 比氟康唑更有效地对抗三种测试的真菌菌株中的两种。这里介绍的研究为开发新型抗真菌剂提供了一种新的结构类型。
• 一种吡喹酮的合成方法
  申请人：江苏诚信药业有限公司

  公开号：CN111072656B

  公开（公告）日：2022-11-25

  本发明提供一种吡喹酮的合成方法，所述方法包括以下步骤：(1)β‑苯乙胺与氯乙酰氯，在水作为溶剂的情况下，于碱性条件进行酰化反应，而后向反应混合物中加入式I所示氨基物，反应得到式II所示化合物，(2)式II所示化合物在环合剂的作用下发生环合反应，而后在碱性环境下与环己甲酰氯反应得到所述吡喹酮。本发明所述方法成本低，反应条件温和，操作方法简单可控，避免反应过程大量有机溶剂的使用，绿色环保，安全性好，产品质量稳定，所得产品符合药用要求。
• 2-(CYCLIC AMINO)-PYRIMIDONE DERIVATIVES
  申请人：Fukunaga Kenji

  公开号：US20090233918A1

  公开（公告）日：2009-09-17

  A compound represented by the formula (I), an optically active isomer thereof, or a pharmaceutical acceptable salt thereof: wherein R 2 represents a hydrogen or the like; R 3 represents methyl group or the like; R 20 represents a halogen atom or the like; q represents an integer of 0 to 3; Z represent nitrogen atom, CH, or the like; R 4 represents hydrogen or the like; R 5 represents hydrogen or the like; R 6 represents a substituted alkyloxy and the like; p represents an integer of 0 to 3; X represents bond, CH 2 , oxygen atom, NH, or the like; any one or more of R 5 and R 6 , R 5 and R 4 , R 6 and R 4 , X and R 5 , X and R 4 , X and R 6 , and R 6 and R 6 may combine to each other to form a ring, which is used for preventive and/or therapeutic treatment of a disease caused by tau protein kinase 1 hyperactivity such as a neurodegenerative diseases (e.g. Alzheimer disease).

  化合物的化学式为（I），其手性异构体或药物可接受的盐：其中，R2代表氢或类似物；R3代表甲基基团或类似物；R20代表卤素原子或类似物；q表示0到3的整数；Z代表氮原子，CH或类似物；R4代表氢或类似物；R5代表氢或类似物；R6代表取代的烷氧基或类似物；p表示0到3的整数；X代表键，CH2，氧原子，NH或类似物；R5和R6，R5和R4，R6和R4，X和R5，X和R4，X和R6以及R6和R6中的任何一个或多个可以结合形成环，用于预防和/或治疗由tau蛋白激酶1过度活化引起的疾病，例如神经退行性疾病（例如阿尔茨海默病）。
• 2-(cyclic amino)-pyrimidone derivatives
  申请人：Fukunaga Kenji

  公开号：US08569294B2

  公开（公告）日：2013-10-29

  A compound represented by the formula (I), an optically active isomer thereof, or a pharmaceutical acceptable salt thereof: wherein R2 represents a hydrogen or the like; R3 represents methyl group or the like; R20 represents a halogen atom or the like; q represents an integer of 0 to 3; Z represent nitrogen atom, CH, or the like; R4 represents hydrogen or the like; R5 represents hydrogen or the like; R6 represents a substituted alkyloxy and the like; p represents an integer of 0 to 3; X represents bond, CH2, oxygen atom, NH, or the like; any one or more of R5 and R6, R5 and R4, R6 and R4, X and R5, X and R4, X and R6, and R6 and R6 may combine to each other to form a ring, which is used for preventive and/or therapeutic treatment of a disease caused by tau protein kinase 1 hyperactivity such as a neurodegenerative diseases (e.g. Alzheimer disease).

  化合物的化学式为（I），其手性异构体或其药学上可接受的盐：其中，R2代表氢或类似物；R3代表甲基基团或类似物；R20代表卤素原子或类似物；q代表0到3的整数；Z代表氮原子，CH或类似物；R4代表氢或类似物；R5代表氢或类似物；R6代表取代的烷氧基或类似物；p代表0到3的整数；X代表键，CH2，氧原子，NH或类似物；R5和R6，R5和R4，R6和R4，X和R5，X和R4，X和R6以及R6和R6中的任意一个或多个可以相互组合形成环，用于预防和/或治疗由tau蛋白激酶1过度活化引起的疾病，例如神经退行性疾病（例如阿尔茨海默病）。