3-(thiophen-2-yl)pyridin-2(1H)-one | 30236-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(thiophen-2-yl)pyridin-2(1H)-one
• 英文别名: 3--pyridon-2；3-thiophen-2-yl-1H-pyridin-2-one；2-Hydroxy-3-(thiophen-2-YL)pyridine；3-thiophen-2-yl-1H-pyridin-2-one
• CAS: 30236-48-7
• 化学式: C₉H₇NOS
• mdl: MFCD18311917
• 分子量: 177.227
• InChiKey: IIAAHZBEMDRXCR-UHFFFAOYSA-N

物化性质

• 沸点：
  441.6±45.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(thiophen-2-yl)pyridin-2(1H)-one 在 sodium hydride 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 14.33h， 生成 1,2-dihydro-1-<<5(4)-methyl-4(5)-imidazolyl>methyl>-2-oxo-3-(2-thienyl)pyridine
  参考文献：
  名称：

  Novel 5-HT3 antagonists. Isoquinolinones and 3-aryl-2-pyridones

  摘要：

  Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists are described. The key pharmacophoric elements were defined as a basic nitrogen, a group capable of hydrogen bonding interactions, and an aromatic moiety. 1,2-Dihydro-2-oxopyridine moiety could be a good linking group because of its nicely planar structure. The steric limitations of the aromatic moiety were investigated by X-ray analysis and computer analysis and shown to be optimal when the aromatic moiety was constrained within an arched planar system, which could be successfully replaced by 3-(2-thienyl)-2-oxopyridine function or 6-amino-7-chloro-1-isoquinolinone function without any loss of the activity. Among the synthesized compounds, 42 showed the most potent activity in the inhibition of Bezold-Jarisch reflex in rats. Compounds 44a and 64 were orally active in the protection against cisplatin-induced emesis in dogs or ferrets. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00096a001
• 作为产物：
  描述：

  噻吩 、 3-溴-2-羟基吡啶 在 palladium diacetate 、 caesium carbonate 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以63%的产率得到3-(thiophen-2-yl)pyridin-2(1H)-one
  参考文献：
  名称：

  钯催化的 5-卤代嘧啶和 5-卤代嘧啶核苷与 TBAF 促进的芳烃和杂芳烃的直接芳基化

  摘要：

  1 - N-苄基-5-碘（或溴）尿嘧啶在 DMF 中存在 TBAF 的情况下与苯和其他简单芳烃进行 Pd 催化的 [Pd 2 (dba) 3 ] 直接芳基化，而无需添加任何配体或5-芳基化尿嘧啶类似物的添加剂。即使只有少量过量的杂芳烃，TBAF 促进的偶联也会在 100 °C (1 小时) 下与富电子杂芳烃有效发生。该协议避免使用芳基硼酸或锡烷前体来合成 5-（2-呋喃基、或 2-噻吩基或 2-吡咯基）尿嘧啶核苷，这些核苷用作重要的 RNA 和 DNA 荧光探针。1 - N-苄基-3- N的事实-methyl-5-iodouracil 没有与芳烃或杂芳烃进行 TBAF 促进的偶联，这表明 C4-醇盐（尿嘧啶的烯醇形式）通过参与从芳烃中提取氢的分子内过程促进偶联。TBAF 促进的芳基化扩展到其他可烯醇化的杂环系统，如 3-bromo-2-pyridone。在 DMF 中存在 Pd(OAc) 2

  DOI：

  10.1021/jo500602p

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXO WELLCOME MFG PTE LTD

  公开号：WO2011075559A1

  公开（公告）日：2011-06-23

  The present invention relates to novel NADPH oxidase II inhibitors and their use in the treatment of diseases mediated by the NADPH oxidase II enzyme.

  本发明涉及新型NADPH氧化酶II抑制剂及其在治疗由NADPH氧化酶II酶介导的疾病中的应用。
• NOVEL COMPOUNDS
  申请人：Chen Deborah

  公开号：US20120252805A1

  公开（公告）日：2012-10-04

  The present invention relates to novel NADPH oxidase II inhibitors and their use in the treatment of diseases mediated by the NADPH oxidase II enzyme.

  本发明涉及新型NADPH氧化酶II抑制剂及其在治疗由NADPH氧化酶II酶介导的疾病中的应用。
• US9029545B2
  申请人：——

  公开号：US9029545B2

  公开（公告）日：2015-05-12
• Palladium-Catalyzed Direct Arylation of 5-Halouracils and 5-Halouracil Nucleosides with Arenes and Heteroarenes Promoted by TBAF
  作者：Yong Liang、Jennifer Gloudeman、Stanislaw F. Wnuk

  DOI：10.1021/jo500602p

  日期：2014.5.2

  undergo the TBAF-promoted couplings with arenes or heteroarenes suggests that the C4-alkoxide (enol form of uracil) facilitates coupling by participation in the intramolecular processes of hydrogen abstraction from arenes. TBAF-promoted arylation was extended into the other enolizable heterocyclic systems such as 3-bromo-2-pyridone. The π-excessive heteroarenes also coupled with 5-halouracils in the

  1 - N-苄基-5-碘（或溴）尿嘧啶在 DMF 中存在 TBAF 的情况下与苯和其他简单芳烃进行 Pd 催化的 [Pd 2 (dba) 3 ] 直接芳基化，而无需添加任何配体或5-芳基化尿嘧啶类似物的添加剂。即使只有少量过量的杂芳烃，TBAF 促进的偶联也会在 100 °C (1 小时) 下与富电子杂芳烃有效发生。该协议避免使用芳基硼酸或锡烷前体来合成 5-（2-呋喃基、或 2-噻吩基或 2-吡咯基）尿嘧啶核苷，这些核苷用作重要的 RNA 和 DNA 荧光探针。1 - N-苄基-3- N的事实-methyl-5-iodouracil 没有与芳烃或杂芳烃进行 TBAF 促进的偶联，这表明 C4-醇盐（尿嘧啶的烯醇形式）通过参与从芳烃中提取氢的分子内过程促进偶联。TBAF 促进的芳基化扩展到其他可烯醇化的杂环系统，如 3-bromo-2-pyridone。在 DMF 中存在 Pd(OAc) 2
• Novel 5-HT3 antagonists. Isoquinolinones and 3-aryl-2-pyridones
  作者：Toshiaki Matsui、Tsuneyuki Sugiura、Hisao Nakai、Sadahiko Iguchi、Satoshi Shigeoka、Hideo Takada、Yoshihiko Odagaki、Yuhki Nagao、Yasuyuki Ushio

  DOI：10.1021/jm00096a001

  日期：1992.9

  Synthesis and pharmacological evaluation of a series of 1,2-dihydro-1-[(5-methyl-1-imidazol-4-yl)methyl]-2-oxopyridine 5-HT3 antagonists are described. The key pharmacophoric elements were defined as a basic nitrogen, a group capable of hydrogen bonding interactions, and an aromatic moiety. 1,2-Dihydro-2-oxopyridine moiety could be a good linking group because of its nicely planar structure. The steric limitations of the aromatic moiety were investigated by X-ray analysis and computer analysis and shown to be optimal when the aromatic moiety was constrained within an arched planar system, which could be successfully replaced by 3-(2-thienyl)-2-oxopyridine function or 6-amino-7-chloro-1-isoquinolinone function without any loss of the activity. Among the synthesized compounds, 42 showed the most potent activity in the inhibition of Bezold-Jarisch reflex in rats. Compounds 44a and 64 were orally active in the protection against cisplatin-induced emesis in dogs or ferrets. Structure-activity relationships are discussed.