2-nitro-1-(2,4,5-trifluorophenyl)ethanone | 156152-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-nitro-1-(2,4,5-trifluorophenyl)ethanone
• CAS: 156152-90-8
• 化学式: C₈H₄F₃NO₃
• 分子量: 219.12
• InChiKey: OPYMKWQCWNCVLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-nitro-1-(2,4,5-trifluorophenyl)ethanone 在 sodium tetrahydroborate 作用下， 生成 (2R,3S)-5-methylene-3-nitro-2-(2,4,5 trifluorophenyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Novel tetrahydropyran analogs as dipeptidyl peptidase IV inhibitors: Profile of clinical candidate (2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-amine (23)

  摘要：

  A series of novel tri-2,3,5-substituted tetrahydropyran analogs were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-4) for the treatment of type 2 diabetes. Optimization of the series provided inhibitors with good DPP-4 potency and selectivity over other peptidases (QPP, DPP8, and FAP). Compound 23, which is very potent, selective, efficacious in the diabetes PD model, and has an excellent pharmacokinetic profile, is selected as a clinical candidate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.061
• 作为产物：
  描述：

  2,4,5-三氟苯甲酰氯 在 sodium hydride 作用下， 反应 4.0h， 生成 2-nitro-1-(2,4,5-trifluorophenyl)ethanone
  参考文献：
  名称：

  1-取代的3-硝基喹啉-4（1 H）-ones的合成

  摘要：

  通过合成6,7-二氟衍生物7a-c证明了一种由相应的2-氟-α-硝基苯乙酮制备1-取代的3-硝基喹啉-4（1 H）-酮的通用合成方法。该方法包括先用原甲酸三乙酯和适当的胺顺序处理起始硝基乙酰苯，然后在温和条件下进行亲核环化反应。的C-7氟原子7可以通过环状胺置换。以这种方式制备了取代的6-氟-7-（4-甲基-1-哌嗪基）-3-硝基喹啉-4（1H）-酮8a-c。

  DOI：

  10.1002/jhet.5570310232

文献信息

• Aminotetrahydropyrans as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes
  申请人：Biftu Tesfaye

  公开号：US20070232676A1

  公开（公告）日：2007-10-04

  The present invention is directed to novel substituted aminotetrahydropyrans of structural formula I which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式I的新型取代氨基四氢吡喃化合物，这些化合物是二肽基肽酶-IV酶的抑制剂，可用于治疗或预防二肽基肽酶-IV酶参与的疾病，如糖尿病，特别是2型糖尿病。该发明还涉及包含这些化合物的药物组合物以及这些化合物和组合物在预防或治疗二肽基肽酶-IV酶参与的这类疾病中的用途。
• AMINOTETRAHYDROPYRANS AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
  申请人：Biftu Tesfaye

  公开号：US20100120863A1

  公开（公告）日：2010-05-13

  The present invention is directed to novel substituted aminotetrahydropyrans of structural formula I which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式I的新型取代氨基四氢吡喃衍生物，它们是二肽基肽酶-IV酶的抑制剂，可用于治疗或预防二肽基肽酶-IV酶参与的疾病，如糖尿病，特别是2型糖尿病。该发明还涉及包含这些化合物的药物组合物，以及这些化合物和组合物在预防或治疗二肽基肽酶-IV酶参与的疾病中的用途。
• [EN] AMINOTETRAHYDROPYRANS AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES<br/>[FR] AMINOTÉTRAHYDROPANES UTILISÉS COMME INHIBITEURS DE LA DIPEPTYL PEPTIDASE-IV POUR TRAITER OU PRÉVENIR LE DIABÈTE
  申请人：MERCK SHARP & DOHME

  公开号：WO2011028455A1

  公开（公告）日：2011-03-10

  The present invention is directed to novel substituted aminotetrahydropyrans of structural formula I which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式I的新型取代氨基四氢吡喃衍生物，它们是二肽基肽酶-IV酶的抑制剂，并且在治疗或预防二肽基肽酶-IV酶参与的疾病，如糖尿病，特别是2型糖尿病方面具有用途。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗二肽基肽酶-IV酶参与的这类疾病中使用这些化合物和组合物。
• Synthesis of 1-substituted 3-nitroquinolin-4(1<i>H</i>)-ones
  作者：Stanislav Radl、Ka-Kong Chan

  DOI：10.1002/jhet.5570310232

  日期：1994.3

  synthetic method for preparing 1-substituted 3-nitroquinolin-4(1H)-ones from corresponding 2-fluoro-α-nitroacetophenones is demonstrated by the synthesis of 6,7-difluoro derivatives 7a-c. The method involves sequential treatment of the starting nitroacetophenone with triethyl orthoformate and the appropriate amine, followed by a nucleophilic cyclization reaction under mild conditions. The C-7 fluorine atom

  通过合成6,7-二氟衍生物7a-c证明了一种由相应的2-氟-α-硝基苯乙酮制备1-取代的3-硝基喹啉-4（1 H）-酮的通用合成方法。该方法包括先用原甲酸三乙酯和适当的胺顺序处理起始硝基乙酰苯，然后在温和条件下进行亲核环化反应。的C-7氟原子7可以通过环状胺置换。以这种方式制备了取代的6-氟-7-（4-甲基-1-哌嗪基）-3-硝基喹啉-4（1H）-酮8a-c。
• [EN] AMINOTETRAHYDROPYRANS AS DIPEPTIDYL PEPTIDASE-IV INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES<br/>[FR] AMINOTÉTRAHYDROPYRANES EN TANT QU'INHIBITEURS DE DIPEPTIDYLE PEPTIDASE-IV POUR LE TRAITEMENT OU LA PRÉVENTION DU DIABÈTE
  申请人：MERCK SHARP & DOHME

  公开号：WO2010056708A1

  公开（公告）日：2010-05-20

  The present invention is directed to novel substituted aminotetrahydropyrans of structural formula I which are inhibitors of the dipeptidyl peptidase-IV enzyme and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly Type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及结构式I的新型取代氨基四氢吡喃衍生物，其是二肽基肽酶IV酶的抑制剂，并且在治疗或预防二肽基肽酶IV酶参与的疾病，如糖尿病和特别是2型糖尿病方面非常有用。本发明还涉及包含这些化合物的制药组合物，以及在预防或治疗二肽基肽酶IV酶参与的这些疾病方面使用这些化合物和组合物。