3-benzyl-2-pyridone | 32967-14-9

• 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-benzyl-2-pyridone
• 英文别名: Benzyl 2-pyridyl alcohol；3-benzyl-1H-pyridin-2-one
• CAS: 32967-14-9
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: RKIOBDYNFLHVQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-benzyl-2-pyridone 在 <4-CH3OC6H4P(S)S>2 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以35%的产率得到3-benzylpyridine-2-thione
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051
• 作为产物：
  描述：

  3-苄基吡啶 在 sodium hydroxide 、 乙酸酐 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 3-benzyl-2-pyridone
  参考文献：
  名称：

  3-aralkyl-2-mercaptoyridines as dopamine-.beta.-hydroxylase inhibitors

  摘要：

  揭示了新颖的结构为3-芳基基-2-巯基吡啶的取代物，其制备方法，制备中有用的中间体，含有它们的药物组合物以及它们在特定治疗中的用途，尤其是作为多巴胺-β-羟化酶抑制剂。

  公开号：

  US04839371A1

文献信息

• [EN] SUBSTITUTED AMINOPROPIONIC DERIVATIVES AS NEPRILYSIN INHIBITORS<br/>[FR] DÉRIVÉS AMINOPROPIONIQUES SUBSTITUÉS COMME INHIBITEURS DE NÉPRILYSINE
  申请人：NOVARTIS AG

  公开号：WO2010136493A1

  公开（公告）日：2010-12-02

  The present invention provides a compound of formula I' or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R5, B1, X and n are defined herein. The invention also relates a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了公式I'的化合物或其药学上可接受的盐，其中R1、R2、R3、R5、B1、X和n在此定义。本发明还涉及一种制造所述化合物的方法及其治疗用途。本发明进一步提供了药理活性剂的组合和药物组合物。
• Solvent-Free Benzylations of 2-Pyridone. Regiospecific<i>N</i>- or<i>C</i>-Alkylation
  作者：Inés Almena、Angel Díaz-Ortiz、Enrique Díez-Barra、Antonio de la Hoz、André Loupy

  DOI：10.1246/cl.1996.333

  日期：1996.5

  Regiospecific N- or C-benzylations of 2-pyridone are observed in solvent-free conditions in the absence of base. The regioselectivity is controlled by the heating technique (microwave irradiation or conventional heating) or, using microwaves, by the emitted power or the leaving group of benzyl halides.

  在无溶剂且无碱的条件下，观察到2-吡啶酮的N-或C-苄基化反应的位向选择性。位向选择性受加热方式（微波照射或传统加热）的控制，或通过微波加热时发射功率或苄烷基卤化物的离去基团进行调节。
• Selectivity under microwave irradiation. Benzylation of 2-pyridone: an experimental and theoretical study
  作者：Antonio de la Hoz、María Pilar Prieto、Michel Rajzmann、Abel de Cózar、Angel Díaz-Ortiz、Andrés Moreno、Fernando P. Cossío

  DOI：10.1016/j.tet.2008.06.052

  日期：2008.8

  conditions. Under microwave irradiation N-alkylation through an SN1-type mechanism (mechanism C) can also occur. The dependence of the outcome of N-alkylation on the benzyl bromide ratio has been explained by a shift in the mechanism from SN2 to SN1 under microwave irradiation. Computational calculations have shown to be a useful tool for determination of the origin of the selectivity under microwave irradiation

  实验研究和通过计算方法研究了2-吡啶酮与苄基溴在不存在碱和无溶剂条件下的反应。该反应是最早报道的实施例之一，其中观察到在微波辐射下选择性的改变。根据苄基卤化物和加热系统，获得C-和/或N-烷基化。N-烷基化通过机构A（S Ñ 2机构）动力学有利的，而C-烷基化通过S Ñ 1型机理热力学上是有利和微波照射下观察到。已经计算出两个S N 1型机制（机制B和C），机制C是S N的一种一世。研究了吡啶酮/苄基溴比率的影响。吡啶酮的第二个分子可稳定过渡态，并有助于溴离子的离开。在这些条件下热力学控制的优势解释了在微波辐射下C-烷基化的发生。在微波辐射下，也可能通过S N 1型机理发生N-烷基化（机理C）。N-烷基化的结果对苄基溴化物比率的依赖性已经通过在微波辐射下从S N 2到S N 1的机理的转变来解释。计算计算已被证明是确定微波辐射下选择性起源的有用工具。
• Enantioselectivity in visible light-induced, singlet oxygen [2+4] cycloaddition reactions (type II photooxygenations) of 2-pyridones
  作者：Christian Wiegand、Eberhardt Herdtweck、Thorsten Bach

  DOI：10.1039/c2cc35621j

  日期：——

  3-Substituted 2-pyridones were enantioselectively (68-90% ee) converted into the respective 3-hydroxypyridine-2,6-diones by a sequence consisting of a template-mediated type II photooxygenation and an acid-catalysed rearrangement.

  通过由模板介导的II型光氧化和酸催化的重排组成的序列，将3-取代的2-吡啶酮对映体选择性地（68-90％ee）转化为相应的3-羟基吡啶-2，6-二酮。
• Nitrogenous heterocyclic derivative, medicinal composition containing the same, medical use thereof, and intermediate therefor
  申请人：Nishimura Toshihiro

  公开号：US20050049203A1

  公开（公告）日：2005-03-03

  The present invention provides nitrogen-containing heterocyclic derivatives represented by the general formula: wherein X 1 and X 3 independently represent N or CH; X 2 represents N or CR 2 ; X 4 represents N or CR 3 ; and with the proviso that one or two of X 1 , X 2 , X 3 and X 4 represent N; R 1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkoxy-substituted (lower alkyl) group, a lower alkoxy-substituted(lower alkoxy) group, a lower alkoxy(lower alkoxy) -substituted (lower alkyl) group, a cyclic lower alkyl group, a halo(lower alkyl) group or a group represented by the general formula: HO-A—wherein A represents a lower alkylene group, a lower alkyleneoxy group or a lower alkylenethio group; R 2 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cyclic lower alkyl group, a lower alkoxy group, an amino group, a (lower acyl)amino group, a mono(lower alkyl)amino group or a di(lower alkyl)amino group; and R 3 represents a hydrogen atom or a lower alkyl group, or pharmaceutically acceptable salts thereof, or prodrugs thereof which are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications or obesity, pharmaceutical compositions comprising the same, and pharmaceutical uses and production intermediates thereof.

  本发明提供了一种以通式表示的含氮杂环衍生物： 其中，X1和X3独立地表示N或CH；X2表示N或CR2；X4表示N或CR3；并且假定X1、X2、X3和X4中的一个或两个表示N；R1表示氢原子、卤素原子、低碳基、低烷氧基、低硫代烷基、低烷氧基取代的（低烷基）基团、低烷氧基取代的（低烷氧基）基团、低烷氧基（低烷氧基）取代的（低烷基）基团、环状低烷基、卤素（低烷基）基团或由通式HO-A-表示的基团，其中A表示低碳亚烷基、低碳亚烷氧基或低碳亚烷硫基；R2表示氢原子、卤素原子、低碳基、环状低碳基、低烷氧基、氨基、（低酰基）氨基、单（低烷基）氨基或双（低烷基）氨基；R3表示氢原子或低碳基，或其药学上可接受的盐，或其前药，其作为预防或治疗与高血糖相关的疾病，如糖尿病、糖尿病并发症或肥胖症的药剂，包括这些药剂的制剂和制备中间体。