1-[4-(吗啉-4-磺酰基)-苯基]-乙酮 | 58722-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[4-(吗啉-4-磺酰基)-苯基]-乙酮
• 英文名称: 1-(4-(morpholinosulfonyl)phenyl)ethanone
• 英文别名: 1-[4-(Morpholine-4-sulfonyl)-phenyl]-ethanone；1-(4-morpholin-4-ylsulfonylphenyl)ethanone
• CAS: 58722-35-3
• 化学式: C₁₂H₁₅NO₄S
• mdl: MFCD00579865
• 分子量: 269.321
• InChiKey: VPKDMMVZORPXFJ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-156 °C
• 沸点：
  448.0±55.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  1-[4-(吗啉-4-磺酰基)-苯基]-乙酮 在 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 N-(1-methylpiperidin-4-yl)-4-(4-(morpholinosulfonyl)phenyl)pyrimidin-2-amine
  参考文献：
  名称：

  Discovery of piperidinyl aminopyrimidine derivatives as IKK-2 inhibitors

  摘要：

  A serine-threonine kinase IKK-2 plays an important role in activation of NF-kappa B through phosphorylation of the inhibitor of NF-kappa B (I kappa B). As NF-kappa B is a major transcription factor that regulates genes responsible for cell proliferation and inflammation, development of selective IKK-2 inhibitors has been an important area of anti-inflammatory and anti-cancer research. In this study, to obtain active and selective IKK-2 inhibitors, various substituents were introduced to a piperidinyl aminopyrimidine core structure. The structure-activity relationship study indicated that hydrogen, methanesulfonyl, and aminosulfonyl groups substituted at the piperidinylamino functionality provide high inhibitory activity against IKK-2. Also, morpholinosulfonyl and piperazinosulfonyl group substituted at the aromatic ring attached to the aminopyrimidine core significantly increased the inhibitory activity of the resulting derivatives. In particular, compound 17 with the aromatic piperazinosulfonyl substituent showed the most potent (IC50 = 1.30 mu M) and selective (over other kinases such as p38 alpha, p38 beta, JNK1, JNK2, JNK3, and IKK-1) inhibitory activity against IKK-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.044
• 作为产物：
  描述：

  4-碘代苯乙酮 在 sodium hypochlorite 、 双(二氧化硫)-1,4-二氮杂双环[2.2.2]辛烷加合物 、 palladium diacetate 、 正丁基二(1-金刚烷基)膦 作用下， 以 水 、 异丙醇 为溶剂， 反应 17.5h， 生成 1-[4-(吗啉-4-磺酰基)-苯基]-乙酮
  参考文献：
  名称：

  利用钯催化芳基碘硫化的一锅磺酰胺合成

  摘要：

  芳基亚磺酸铵，方便地由芳基碘化物和二氧化硫替代物 DABSO 制备，在钯 (0) 催化剂的作用下，在一锅法中转化为各种功能化的磺酰胺。亚磺酸盐向磺酰胺的转化是通过用相关胺和次氯酸钠（漂白剂）的水溶液进行简单处理来实现的。广泛的胺，包括苯胺和氨基酸衍生物，可与各种芳基碘有效结合，产生高产率的磺胺类药物。

  DOI：

  10.1055/s-0035-1560578

文献信息

• S(<scp>vi</scp>) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling
  作者：Xuefeng Wang、Min Yang、Shengqing Ye、Yunyan Kuang、Jie Wu

  DOI：10.1039/d1sc01351c

  日期：——

  Sulfuric chloride is used as the source of the –SO2– group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki–Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results

  在钯催化的三组分磺酰胺合成中，氯化硫被用作-SO 2-基团的来源。原位生成的氨磺酰氯与硼酸之间的Suzuki-Miyaura偶联以中等至高收率产生了多种磺酰胺，并具有出色的反应选择性。尽管此转化不适用于伯胺或苯胺，但结果表明官能团耐受性高。通过解决脱磺酰化问题并利用廉价且容易获得的氯化硫作为二氧化硫的来源，首先实现了氧化还原中性三组分合成的磺酰胺。
• [EN] PYRAZOLONE DERIVATIVES AS NITROXYL DONORS<br/>[FR] DÉRIVÉS DE PYRAZOLONE UTILISÉS EN TANT QUE DONNEURS DE NITROXYLE
  申请人：CARDIOXYL PHARMACEUTICALS INC

  公开号：WO2015183839A1

  公开（公告）日：2015-12-03

  The disclosed subject matter provides pyrazolone derivative compounds, pharmaceutical compositions comprising such compounds, kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

  所披露的主题提供了吡唑酮衍生物化合物，包括这些化合物的药物组合物，包括这些化合物的试剂盒，以及使用这些化合物或药物组合物的方法。具体而言，所披露的主题提供了使用这些化合物或药物组合物治疗心力衰竭的方法。
• Anilinopyrimidine derivatives as JNK pathway inhibitors and compositions and methods related thereto
  申请人：——

  公开号：US20030220330A1

  公开（公告）日：2003-11-27

  Compounds having activity as inhibitors of the JNK pathway are disclosed. The compounds of this invention are anilinopyrimidine derivatives having the following structure: 1 wherein R 1 through R 6 are as defined herein. Such compounds have utility in the treatment of a wide range of conditions that are responsive to inhibition of the JNK pathway. Thus, methods of treating such conditions are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.

  本发明揭示了作为JNK通路抑制剂活性的化合物。本发明的化合物是具有以下结构的苯胺吡嘧啶衍生物：其中R1至R6如本文所定义。这些化合物在治疗对JNK通路抑制敏感的广泛疾病方面具有用途。因此，本文还揭示了治疗这些疾病的方法，以及含有上述化合物中的一个或多个化合物的药物组合物。
• Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto
  申请人：——

  公开号：US20030203926A1

  公开（公告）日：2003-10-30

  Compounds having activity as inhibitors of IKK are disclosed, particularly IKK-2. The compounds of this invention are anilinopyrimidine derivatives having the following structure: 1 wherein R 1 and R 6 are as defined herein. Such compounds have utility in the treatment of a wide range of conditions that are responsive to IKK inhibition. Thus, methods of treating such conditions are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.

  本发明揭示了作为IKK抑制剂的化合物，特别是IKK-2。本发明的化合物是具有以下结构的苯胺嘧啶衍生物：1其中R1和R6如本文所定义。这些化合物在治疗对IKK抑制有响应的各种疾病方面具有实用性。因此，本文还揭示了治疗这些疾病的方法，以及含有上述化合物之一或多个化合物的药物组合物。
• Methods for treating or preventing an inflammatory or metabolic condition or inhibiting JNK
  申请人：——

  公开号：US20040106634A1

  公开（公告）日：2004-06-03

  This invention generally relates to methods for treating or preventing a condition responsive to JNK inhibition, such as a metabolic condition, comprising administering to a patient in need thereof an effective amount of an Anilinopyrimidine Derivative having the following structure: 1 or a pharmaceutically acceptable salt thereof, wherein R 1 through R 6 are as defined herein.

  这项发明通常涉及用于治疗或预防对JNK抑制敏感的疾病的方法，例如代谢状况，包括向需要的患者施用具有以下结构的Anilinopyrimidine衍生物的有效剂量：1或其药用可接受盐，其中R1至R6如本文所定义。