1,2-dihydro-4-[(4-ethylphenyl)-methyl]-5-(trifluoromethyl)-3H-pyrazole-3-one | 152595-73-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 1,2-dihydro-4-[(4-ethylphenyl)-methyl]-5-(trifluoromethyl)-3H-pyrazole-3-one
• 英文别名: 1,2-dihydro-4-[(4-ethylphenyl) methyl]-5-(trifluoromethyl)-3H-pyrazole-3-one；1,2-dihydro-4-[(4-ethylphenyl)methyl]-5-(trifluoromethyl)-3H-pyrazole-3-one；1,2-Dihydro-4-[(4-ethylphenyl)methyl]-5-(trifluoromethyl)-3H-pyrazol-3-one；1,2-dihydro-4-[(4-ethylphenyl)methyl]-5-trifluoromethyl-3H-pyrazol-3-one；4-[(4-ethylphenyl)methyl]-1,2-dihydro-5-trifluoromethyl-3H-pyrazol-3-one；4-[(4-ethylphenyl)methyl]-5-(trifluoromethyl)-1,2-dihydropyrazol-3-one
• CAS: 152595-73-8
• 化学式: C₁₃H₁₃F₃N₂O
• 分子量: 270.254
• InChiKey: YHSHHEBBJFZVDP-UHFFFAOYSA-N

物化性质

• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-4-[(4-ethylphenyl)-methyl]-5-(trifluoromethyl)-3H-pyrazole-3-one 在 palladium dihydroxide 、 ethyl azodicarboxylate 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 9.5h， 生成 4-((4-ethylphenyl)methyl)-5-(trifluoromethyl)-1H-pyrazol-3-yl-β-D-glucopyranoside uronic acid
  参考文献：
  名称：

  Pyrazole-O-glucosides as novel Na+-glucose cotransporter (SGLT) inhibitors

  摘要：

  O-glucuronides and O-glucosides of a series of pyrazoles analogues were synthesized and evaluated for their SGLT inhibitory activity in brush border membrane vehicles (BBMVs) of rat kidney. O-glucosides of certain pyrazole analogues inhibited the transport of [C-14]-glucose in BBMVs, and induced glucosuria in Wistar rats by intravenous injection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00466-9
• 作为产物：
  描述：

  1-(溴甲基)-4-乙基苯 在 sodium hydride 、 肼 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 生成 1,2-dihydro-4-[(4-ethylphenyl)-methyl]-5-(trifluoromethyl)-3H-pyrazole-3-one
  参考文献：
  名称：

  db / db小鼠中的新型强效降糖药：（4-取代的苄基）（三氟甲基）吡唑和-吡唑啉酮的合成及其与构效关系的研究。

  摘要：

  1,2-二氢-4-[[4-（甲硫基苯基）甲基] -5-（三氟甲基）-3H-吡唑-3-酮（SAR）的合成，构效关系（SAR）研究和抗糖尿病特性羟基互变异构体； WAY-123783，4）被描述。将4-甲硫基，甲亚磺酰基或乙基取代为吡唑-3-一的C5处的C5处的苄基，与三氟甲基结合，在肥胖的糖尿病db / db小鼠中产生了有效的降血糖药（血浆降低16-30％）葡萄糖2 mg / kg）。抗血糖作用与在非糖尿病小鼠中观察到的健壮的糖尿（> 8 g / dL）有关。通过酸性氢的单烷基和二烷基化化学捕集七种可能的互变异构形式的杂环中的四种，从而提供了铅4的几种其他有效的类似物（在5 mg / kg时减少了39-43％的还原），以及铅的二烷基化对。显示在正常小鼠中所有活性类似物均产生相关糖尿酸作用分离的区域异构体。在口服和皮下葡萄糖耐量试验中，对WAY-123783铅（ED50 = 9.85 mg /

  DOI：

  10.1021/jm960444z

文献信息

• Pyrazole derivatives and diabetic medicine containing them
  申请人：AJINOMOTO CO. INC

  公开号：US20040006025A1

  公开（公告）日：2004-01-08

  The present invention provides pyrazole-O-glycoside derivatives represented by the following formulae, used as a diabetic medicine. 1

  本发明提供了以下式表示的吡唑-O-糖苷衍生物，用作糖尿病药物。
• Glucopyranosyloxypyrazole derivatives and use thereof in medicines
  申请人：Fujikura Hideki

  公开号：US20060094667A1

  公开（公告）日：2006-05-04

  The present invention provides glucopyranosyloxypyrazole derivatives represented by the general formula: wherein R represents a hydrogen atom, a lower alkyl group or a group forming a prodrug;.one of Q and T represents a group represented by the general formula: (wherein P represents a hydrogen atom or a group forming a prodrug), while the other represents a lower alkyl group or a halo(lower alkyl) group; R 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halo (lower alkyl) group or a halogen atom; and with the proviso that P does not represent a hydrogen atom when R represents a hydrogen atom or a lower alkyl group, or pharmaceutically acceptable salts thereof, which exert an inhibitory activity in human SGLT2 and have an improved oral absorption, and therefore are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications or obesity, and pharmaceutically acceptable salts thereof, and pharmaceutical uses thereof.

  本发明提供了由下式表示的葡萄糖吡唑衍生物： 其中，R表示氢原子，低级烷基或形成前药的基团；Q和T中的一个表示由下式表示的基团： （其中，P表示氢原子或形成前药的基团），而另一个表示低级烷基或卤代（低级烷基）基团；R2表示氢原子，低级烷基，低级烷氧基，低级烷基硫基，卤代（低级烷基）基团或卤素原子；但要注意，当R表示氢原子或低级烷基时，P不表示氢原子。本发明的衍生物在人体SGLT2中具有抑制活性，并具有改善口服吸收，因此可用作预防或治疗与高血糖有关的疾病，如糖尿病、糖尿病并发症或肥胖症的药物，以及其药学上可接受的盐和药物用途。
• Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof
  申请人：Fujikura Hideki

  公开号：US20050261206A1

  公开（公告）日：2005-11-24

  The present invention relates to glucopyranosyloxypyrazole derivatives represented by the general formula: wherein R 1 represents a hydrogen atom or a lower alkyl group; one of Q 1 and T 1 represents a group represented by the general formula: while the other represents a lower alkyl group or a halo(lower alkyl) group; and R 2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halo(lower alkyl) group or a halogen atom, or pharmaceutically acceptable salts thereof, which have an inhibitory activity in human SGLT2 and are useful as agents for the prevention or treatment of diabetes, diabetic complications or obesity, and to pharmaceutical compositions comprising the same and intermediates thereof.

  本发明涉及由下式表示的葡萄糖吡唑衍生物：其中R1代表氢原子或低碳基；Q1和T1中的一个代表由下式表示的基团：另一个代表低碳基或卤代（低碳）基团；R2代表氢原子、低碳基、低烷氧基、低烷硫基、卤代（低碳）基团或卤素原子，或其药学上可接受的盐，具有对人类SGLT2的抑制活性，并且可用作预防或治疗糖尿病、糖尿病并发症或肥胖症的药物，以及包含它们和它们的中间体的制药组合物。
• Prophylactic and therapeutic agent of diabetes mellitus
  申请人：Maezono Katsumi

  公开号：US20050143424A1

  公开（公告）日：2005-06-30

  The invention provides a prophylactic and therapeutic agent of diabetes mellitus, including a combination of an inhibitor of renal glucose reabsorption and a hypoglycemic agent. In accordance with the invention, hyperglycemia after meals, between meals and during fasting can be ameliorated. More specifically, in accordance with the invention, a therapeutic effect of diabetes mellitus as never been obtained by the hypoglycemic agents of the related art can be achieved.

  本发明提供了一种糖尿病的预防和治疗剂，包括肾脏葡萄糖重吸收抑制剂和降糖剂的组合。根据本发明，可以改善餐后、餐间和禁食期间的高血糖。更具体地，根据本发明，可以实现糖尿病的治疗效果，这是以往相关艺术中的降糖药物所未曾达到的。
• N-substituted pyrazole-O-glycoside derivatives and therapeutic agent for diabetes containing the same
  申请人：Ajinomoto Co., Inc.

  公开号：US20040110936A1

  公开（公告）日：2004-06-10

  The present invention relates to pyrazole derivatives represented by the following formulas and analogues thereof, which can be used for a therapeutic agent for diabetes. 1

  本发明涉及以下公式及其类似物所表示的吡唑衍生物，可用作糖尿病治疗药物。1