6-(1-氨基乙基)-2H-1,4-苯并恶嗪-3(4H)-酮 | 159459-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 中文名称: 6-(1-氨基乙基)-2H-1,4-苯并恶嗪-3(4H)-酮
• 英文名称: 6-[1-aminoethyl]-2H-1,4-benzoxazin-3(4H)-one
• 英文别名: 6-(1-aminoethyl)-2H-1,4-benzoxazin-3(4H)-one；6-(1-aminoethyl)-4H-1,4-benzoxazin-3-one
• CAS: 159459-52-6
• 化学式: C₁₀H₁₂N₂O₂
• mdl: MFCD08444636
• 分子量: 192.217
• InChiKey: IDOFUCXHAUJAEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±42.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  6-(1-氨基乙基)-2H-1,4-苯并恶嗪-3(4H)-酮 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzooxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide is a potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability of rat hippocampal neurons

  摘要：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide ((S)-2) was identified as a potent and efficacious KCNQ2 opener. This compound demonstrated significant activity in reducing neuronal hyperexcitability in rat hippocampal slices, and the inhibition mediated by (S)-2 was reversed by the KCNQ blocker linopirdine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.069
• 作为产物：
  描述：

  6-(N-hydroxy-C-methylcarbonimidoyl)-4H-1,4-benzoxazin-3-one 在 镍 ammonium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 以94%的产率得到6-(1-氨基乙基)-2H-1,4-苯并恶嗪-3(4H)-酮
  参考文献：
  名称：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzooxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide is a potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability of rat hippocampal neurons

  摘要：

  (S)-N-[1-(4-Cyclopropylmethyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]-3-(2-fluoro-phenyl)-acrylamide ((S)-2) was identified as a potent and efficacious KCNQ2 opener. This compound demonstrated significant activity in reducing neuronal hyperexcitability in rat hippocampal slices, and the inhibition mediated by (S)-2 was reversed by the KCNQ blocker linopirdine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.069

文献信息

• [EN] 2-METHYL-QUINAZOLINES<br/>[FR] 2-MÉTHYL-QUINAZOLINES
  申请人：BAYER PHARMA AG

  公开号：WO2018172250A1

  公开（公告）日：2018-09-27

  The present invention describes 2-methyl-quinazoline compounds of general formula (I), methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions. The 2-methyl substituted quinazoline compounds of general formula(I) effectively and selectively inhibit the Ras-Sos interaction without significantly targeting the EGFR receptor. They are therefore useful for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, such as cancer as a sole agent or in combination with other active ingredients.

  本发明描述了一般式(I)的2-甲基喹唑啉化合物，制备该化合物的方法，用于制备该化合物的中间体化合物，包含该化合物的药物组合物和组合物，以及用于制造药物组合物的该化合物的用途。一般式(I)的2-甲基取代喹唑啉化合物有效且选择性地抑制Ras-Sos相互作用，而不显著靶向EGFR受体。因此，它们对于治疗或预防疾病特别是高增殖性疾病，如癌症作为单一药剂或与其他活性成分组合使用是有用的。
• Design, synthesis, and structure–activity relationship of a new class of amidinophenylurea-based factor VIIa inhibitors
  作者：Otmar Klingler、Hans Matter、Manfred Schudok、S.Paul Bajaj、Joerg Czech、Martin Lorenz、Hans Peter Nestler、Herman Schreuder、Peter Wildgoose

  DOI：10.1016/s0960-894x(03)00168-9

  日期：2003.4

  Selective inhibition of coagulation factor VIIa has recently gained attraction as interesting approach towards antithrombotic treatment. Using parallel synthesis supported by structure-based design and X-ray crystallography, we were able to identify a novel series of amidinophenylurea derivatives with remarkable affinity for factor VIIa. The most potent compound displays a K(i) value of 23 nM for factor

  凝血因子VIIa的选择性抑制最近作为抗血栓治疗的有趣方法而受到关注。使用基于结构的设计和X射线晶体学支持的平行合成，我们能够鉴定出对因子VIIa具有显着亲和力的一系列新的a基苯基脲衍生物。最有效的化合物显示出VIIa因子的K（i）值为23 nM。
• [EN] NOVEL CALCIUM SENSING RECEPTOR MODULATING COMPOUNDS AND PHARMACEUTICAL USE THEREOF<br/>[FR] NOUVEAUX COMPOSÉS MODULANT LE RÉCEPTEUR SENSIBLE AU CALCIUM, ET LEUR UTILISATION PHARMACEUTIQUE
  申请人：LEO PHARMA AS

  公开号：WO2010136037A1

  公开（公告）日：2010-12-02

  The invention relates to novel calcium-sensing receptor (CaSR) modulating substituted cyclopentylene compounds represented in formula I and derivatives thereof, to said compounds for use as a medicament, to said compounds for use in therapy, to pharmaceutical compositions comprising said compounds, to methods of treating diseases with said compounds, and to the use of said compounds in the manufacture of medicaments.

  该发明涉及一种表示为公式I的新型调节钙感受受体（CaSR）的取代环戊烯化合物及其衍生物，该化合物用作药物，用于治疗的化合物，包含该化合物的制药组合物，使用该化合物治疗疾病的方法以及使用该化合物制造药物。
• Cinnamide derivatives as KCNQ potassium channel modulators
  申请人：——

  公开号：US20030166650A1

  公开（公告）日：2003-09-04

  There is provided novel cinnamide derivatives of Formula I 1 wherein R is C 1-4 alkyl or trifluoromethyl; R 1 is selected from the group consisting of pyridinyl, quinolinyl, thienyl, furanyl, 1,4-benzodioxanyl, 1,3-benzodioxolyl, chromanyl, indanyl, biphenylyl, phenyl and substituted phenyl in which said substituted phenyl is substituted with one or two substituents each independently selected-from the group consisting of halogen, C 1-4 alkyl, C 1-4 alkoxy, trifluoromethyl, trifluoromethoxy and nitro; R 2 and R 3 are each independently selected from the group consisting of hydrogen, C 1-4 alkyl, and halogen; R 4 is selected from the group consisting of di(C 1-4 alkyl)amino, trifluoromethoxy and optionally substituted morpholin-4-yl, pyridinyl, pyrimidinyl, piperazinyl, and pyrazinyl with one or two substituents in which said substituent is independently selected from the group consisting of C 1-4 alkyl, aminomethyl, hydroxymethyl, chloro or fluoro; R 5 is hydrogen, chloro or fluoro; or R 4 and R 5 taken together are —CH═CH—CH═CH— or —X(CH 2 ) m Y— in which X and Y are each independently selected from the group consisting of CH 2 , (CH 2 ) n N(R 9 )— and O, wherein m is 1 or 2; n is 0 or 1; and R 6 , R 7 , and R 8 are each independently selected from hydrogen, chloro and fluoro; and R 9 is selected from the group consisting of hydrogen, C 1-4 alkyl, hydroxyethyl, C 1-4 alkoxyethyl, cyclopropylmethyl, —CO 2 (C 1-4 alkyl), and —CH 2 CH 2 NR 10 R 11 in which R 10 and R 11 are each independently hydrogen or C 1-4 alkyl, which are openers of the KCNQ potassium channels and are useful in the treatment of disorders which are responsive to the opening of the KCNQ potassium channels.

  提供了一种新型的 Formula I1 中的肉桂酰胺衍生物，其中 R 为 C1-4 烷基或三氟甲基；R1 选自吡啶基、喹啉基、噻吩基、呋喃基、1,4-苯并二氧杂基、1,3-苯并二氧杂基、色基、茚基、联苯基、苯基和取代苯基，其中所述取代苯基取代有一个或两个取代基，每个取代基独立地选自卤素、C1-4 烷基、C1-4 烷氧基、三氟甲基、三氟甲氧基和硝基；R2 和 R3 各自独立地选自氢、C1-4 烷基和卤素；R4 选自二(C1-4 烷基)氨基、三氟甲氧基和可选取代的吗啉-4-基、吡啶基、嘧啶基、哌嗪基和吡嗪基，其中所述基带有一个或两个取代基，所述取代基独立地选自 C1-4 烷基、氨甲基、羟甲基、氯或氟；R5 为氢、氯或氟；或者 R4 和 R5 结合成 —CH═CH—CH═CH— 或 —X(CH2)mY—，其中 X 和 Y 各自独立地选自 、( )nN(R9)— 和 O，其中 m 为 1 或 2；n 为 0 或 1；R6、R7 和 R8 各自独立地选自氢、氯和氟；R9 选自氢、C1-4 烷基、羟乙基、C1-4 烷氧乙基、环丙基甲基、—CO2(C1-4 烷基) 和 — NR10R11，其中 R10 和 R11 各自独立地为氢或 C1-4 烷基，这些化合物是 KCNQ 钾通道的开放剂，可用于治疗对 KCNQ 钾通道的开放有反应的疾病。
• [EN] CINNAMIDE DERIVATIVES AS KCNQ POTASSIUM CHANNEL MODULATORS<br/>[FR] DERIVES DE LA CINNAMIDE MODULATEURS DU CANAL POTASSIQUE KCNQ
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2002096858A1

  公开（公告）日：2002-12-05

  There is provided novel cinnamide derivatives of Formula I wherein R is C1-4 alkyl or trifluoromethyl, R1 is selected from the group consisting of pyridinyl, quinolinyl, thienyl, furanyl, 1,4-benzodioxanyl, 1,3-benzodioxolyl, chromanyl, indanyl, biphenylyl, phenyl and substituted phenyl which are openers of the KCNQ potassium channels and are useful in the treatment of disorders which are responsive to the opening of the KCNQ potassium channels.

  提供了一种新的苯甲酰胺衍生物，其化学式为I，其中R为C1-4烷基或三氟甲基，R1选自吡啶基，喹啉基，噻吩基，呋喃基，1,4-苯并二氧杂环基，1,3-苯并二氧杂环基，色甘醇基，茚基，联苯基，苯基和取代苯基，这些化合物是KCNQ钾通道的开放剂，可用于治疗对KCNQ钾通道的开放反应的疾病。