tert-butyl 2-(4-(methylsulfonyl)phenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate | 1002339-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl 2-(4-(methylsulfonyl)phenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate
• 英文别名: tert-butyl 2-[4-(methylsulfonyl)phenyl]-3-oxohexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylate；tert-butyl 2-(4-methylsulfonylphenyl)-3-oxo-5,6,8,8a-tetrahydro-1H-imidazo[1,5-a]pyrazine-7-carboxylate
• CAS: 1002339-44-7
• 化学式: C₁₈H₂₅N₃O₅S
• 分子量: 395.48
• InChiKey: DLUAQWRCKKLRQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  95.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-(methylsulfonyl)phenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以93%的产率得到2-[4-(methylsulfonyl)phenyl]hexahydroimidazo[1,5-a]pyrazin-3(2H)-one hydrochloride
  参考文献：
  名称：

  EP2039695

  摘要：

  公开号：
• 作为产物：
  描述：

  tert-butyl 2-[4-(methylthio)phenyl]-3-oxohexahydroimidazo[1,5-a]pyrazine-7(1H)-carboxylate 在 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以88%的产率得到tert-butyl 2-(4-(methylsulfonyl)phenyl)-hexahydro-3-oxoimidazo[1,5-a]pyrazine-7(1H)-carboxylate
  参考文献：
  名称：

  EP2039695

  摘要：

  公开号：

文献信息

• Convenient Synthesis of Novel 2-Substituted Imidazopyrazinone Derivatives
  作者：Yanyun Zhu、Gonghua Song、Peng Lu、Mingjie Zhu、Yilang Chen

  DOI：10.1080/00397911.2010.525774

  日期：2012.2.15

  Abstract Starting from commercially available piperazine-2-carboxylic acid, a series of novel 2-aryl and 2-benzyl substituted imidazopyrazinone were prepared. The intermediates 5a–g were obtained through facile Buchwald–Hartwig coupling reaction, and the effects of catalyst, base, and solvent on the coupling reaction were investigated. The optimal reaction conditions for the coupling reaction were

  摘要 以市售的哌嗪-2-羧酸为原料，制备了一系列新型的2-芳基和2-苄基取代的咪唑并吡嗪酮。通过简单的 Buchwald-Hartwig 偶联反应获得中间体 5a-g，并研究了催化剂、碱和溶剂对偶联反应的影响。偶联反应的最佳反应条件为PdCl2(dppf)/NaO-t-Bu/甲苯。图形概要
• Bicyclic heterocyclic compound and use thereof
  申请人：Matsumoto Takahiro

  公开号：US20100004249A1

  公开（公告）日：2010-01-07

  The present invention provides a bicyclic heterocyclic compound having a serotonin 5-HT 2C receptor activation action and the like. A compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.

  本发明提供了一种具有血清素5-HT2C受体激活作用等的双环杂环化合物。其中，化合物由式(I)表示，其中每个符号如规范中所定义，或其盐。
• BICYCLIC HETEROCYCLIC COMPOUND AND USE THEREOF
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2039695A1

  公开（公告）日：2009-03-25

  The present invention provides a bicyclic heterocyclic compound having a serotonin 5-HT2c receptor activation action and the like. A compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof.

  本发明提供了一种具有5-羟色胺5-HT2c受体激活作用的双环杂环化合物等。 由式（I）代表的化合物： 其中各符号如说明书中所定义，或其盐。
• Synthesis, biological assay in vitro and molecular docking studies of new imidazopyrazinone derivatives as potential dipeptidyl peptidase IV inhibitors
  作者：Yanyun Zhu、Shuang Xia、Mingjie Zhu、Weiyin Yi、Jiagao Cheng、Gonghua Song、Zhong Li、Peng Lu

  DOI：10.1016/j.ejmech.2010.08.002

  日期：2010.11

  A series of novel imidazopyrazinone derivatives were synthesized and evaluated with regard to their ability to inhibit dipeptidyl peptidase IV (DPP-IV) in vitro. Of these compounds (2R)-4-oxo-4-[2-(3-carbamoylbenzyl)-hexahydro-3-oxoimidazo [1,5-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine fumaric acid (17h, IC50 = 78 nM) was shown to effectively inhibit the activity of the dipeptidyl peptidase IV enzyme. Molecular docking studies were also performed to illustrate the binding mode of compounds 15c and 17h. Favorable interactions were identified from the binding of inhibitor 15c with DPP-IV. By analogy to the binding mode of compound 15c, it seems that the introduction of a substituted benzyl moiety onto the imidazopyrazinone could remarkably improve the inhibitory activity of compound 17h. (C) 2010 Elsevier Masson SAS. All rights reserved.