N-[(2,6-difluorophenylthiocarbamoyl)methyl]-2-(4-methoxyphenoxy)acetamide | 1448524-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[(2,6-difluorophenylthiocarbamoyl)methyl]-2-(4-methoxyphenoxy)acetamide
• 英文别名: N-[2-(2,6-difluoroanilino)-2-sulfanylideneethyl]-2-(4-methoxyphenoxy)acetamide
• CAS: 1448524-14-8
• 化学式: C₁₇H₁₆F₂N₂O₃S
• 分子量: 366.388
• InChiKey: KZJVTHRLQWUVTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲氧基苯氧乙酸 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 N-[(2,6-difluorophenylthiocarbamoyl)methyl]-2-(4-methoxyphenoxy)acetamide
  参考文献：
  名称：

  In silico and pharmacological screenings identify novel serine racemase inhibitors

  摘要：

  D-Serine is a coagonist of the N-methyl-D-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.

  DOI：

  10.1016/j.bmcl.2014.07.003

文献信息

• SERINE RACEMASE INHIBITOR
  申请人：National University Corporation University of Toyama

  公开号：US20140371291A1

  公开（公告）日：2014-12-18

  A novel serine racemase inhibitor exhibits sufficient activity and specificity. The serine racemase inhibitor includes one or more compounds selected from compounds respectively represented by the following general formulas [MM_1], [DR_1], [DR′_1], [LW_1], and [ED_1] as an active ingredient.

  一种新型的丝氨酸外消旋酶抑制剂表现出足够的活性和特异性。该丝氨酸外消旋酶抑制剂包括一种或多种选自以下通用式[MM_1]、[DR_1]、[DR′_1]、[LW_1]和[ED_1]所代表的化合物的化合物作为活性成分。
• US9216954B2
  申请人：——

  公开号：US9216954B2

  公开（公告）日：2015-12-22
• [EN] SERINE RACEMASE INHIBITOR<br/>[FR] INHIBITEUR DE LA SÉRINE RACÉMASE
  申请人：NAT UNIV CORP UNIV TOYAMA

  公开号：WO2013111798A1

  公开（公告）日：2013-08-01

  【課題】本発明は、十分な活性と特異性のある新規なセリンラセマーゼ阻害剤の提供を目的とする。 【解決手段】下記一般式［ＭＭ＿１］、［ＤＲ＿１］、［ＤＲ'＿１］、［ＬＷ＿１］および［ＥＤ＿１］のいずれかの化合物群から選ばれる１つ以上の化合物を有効成分とするセリンラセマーゼ阻害剤。
• In silico and pharmacological screenings identify novel serine racemase inhibitors
  作者：Hisashi Mori、Ryogo Wada、Jie Li、Tetsuya Ishimoto、Mineyuki Mizuguchi、Takayuki Obita、Hiroaki Gouda、Shuichi Hirono、Naoki Toyooka

  DOI：10.1016/j.bmcl.2014.07.003

  日期：2014.8

  D-Serine is a coagonist of the N-methyl-D-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.