(2-aminopyridin-3-yl)(4-chlorophenyl)methanone | 65326-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-aminopyridin-3-yl)(4-chlorophenyl)methanone
• 英文别名: (2-Aminopyridin-3-yl)-(4-chlorophenyl)methanone
• CAS: 65326-81-0
• 化学式: C₁₂H₉ClN₂O
• 分子量: 232.669
• InChiKey: LEVLJFJVKSPVOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.3±40.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-aminopyridin-3-yl)(4-chlorophenyl)methanone 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 5.0h， 以84%的产率得到2-Amino-3-(4-chlorbenzyl)pyridin
  参考文献：
  名称：

  5H-吡啶并[2,3-c]-2-苯并氮杂的合成

  摘要：

  标题化合物可以通过两种不同的方式制备：三环化合物 6、9 和 10 可通过 2-苯并氮杂-烯氨基腈 1 与 C2 结构单元 2、7 和 8 的闭环反应获得。-在第二条路线中，2-氨基-3-苯甲酰基吡啶16a、b被还原为2-氨基-3-苄基吡啶18a、b。18a、b 的苯甲酰化产生二苯甲酰基化合物 20 和 21，它们可以转化为单苯甲酰基化合物 22 和 23。Bischler - Napieralski 反应方式的闭环导致 5H - 吡啶 [2,3 - c] -2 - 苯并氮杂 24a、b 和 25a、b 与 22a、b 和 23a、b。- 使用 1H、13C 和 15NNMR 数据表明，苯甲酰乙亚胺酸乙酯 (12a) 以苯甲酰乙烯酮-O、N-缩醛 12a AE 的形式存在。

  DOI：

  10.1002/ardp.19943270407
• 作为产物：
  描述：

  (4-chlorophenyl)(2-fluoropyridin-3-yl)methanone 在 氨 作用下， 以 乙醇 为溶剂， 生成 (2-aminopyridin-3-yl)(4-chlorophenyl)methanone
  参考文献：
  名称：

  Design, Synthesis, and Activity of a Series of Arylpyrid-3-ylmethanones as Type I Positive Allosteric Modulators of α7 Nicotinic Acetylcholine Receptors

  摘要：

  A series of novel arylpyrid-3-ylmethanones (7a-aa) were designed as modulators of alpha 7 nicotinic acetylcholine receptors (nAChRs). The methanones were found to be type I positive allosteric modulators (PAMs) of human alpha 7 nAChRs expressed in Xenopus ooctyes. Structure-activity relationship (SAR) studies resulted in the identification of compound 7v as a potent and efficacious type I PAM with maximum modulation of a nicotine EC5 response of 1200% and EC50 = 0.18 mu M. Compound 7z was active in reversing the effect of scopolamine in the novel object recognition (NOR) paradigm with a minimum effective ip dose of 1.0 mg/kg (2.7 mu mol/kg). This effect was blocked by the selective alpha 7 nAChR antagonist methyllycaconitine (MLA). These compounds are nAChRs that may have therapeutic value in restoring impaired sensory Alzheimer's disease. potent type I positive allosteric modulators of alpha 7 gating and cognitive deficits in schizophrenia and Alzheimer's disease.

  DOI：

  10.1021/jm400704g

文献信息

• Palladium-Catalyzed Oxidative C–H Bond Coupling of Steered Acetanilides and Aldehydes: A Facile Access to <i>ortho</i>-Acylacetanilides
  作者：Yinuo Wu、Baozhu Li、Fei Mao、Xingshu Li、Fuk Yee Kwong

  DOI：10.1021/ol201201a

  日期：2011.6.17

  A palladium-catalyzed oxidative C–H bond functionalization/ortho-acylation of acetanilides using easily accessible aldehyde as the acyl source is described. In the presence of a Pd(TFA)2 catalyst and tert-butylhydroperoxide at 90 °C in general, an array of ortho-acylacetanilides can be afforded in good yields.

  描述了使用容易获得的醛作为酰基源的钯催化的乙苯胺的氧化CH键官能化/邻位酰化反应。通常在90℃下在Pd（TFA）2催化剂和叔丁基氢过氧化物的存在下，可以良好的收率得到一系列邻-酰基乙酰苯胺。
• Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C–H bond acylation of acetanilides
  作者：Yinuo Wu、Pui Ying Choy、Fei Mao、Fuk Yee Kwong

  DOI：10.1039/c2cc37352a

  日期：——

  A palladium-catalyzed cascade cross-coupling of acetanilide and toluene for the synthesis of ortho-acylacetanilide is described. Toluene derivatives can act as effective acyl precursors (upon sp(3)-C-H bond oxidation by a Pd/TBHP system) in the oxidative coupling between two C-H bonds. This dehydrogenative Pd-catalyzed ortho-acylation proceeds under mild reaction conditions.

  描述了钯催化的乙酰苯胺和甲苯的级联交叉偶联，用于合成邻酰基乙酰苯胺。甲苯衍生物在两个CH键之间的氧化偶联中可以充当有效的酰基前体（在sp（3）-CH键上通过Pd / TBHP系统氧化）。这种脱氢的Pd催化的邻位酰化反应在温和的反应条件下进行。
• CYTOKINE PRODUCTION INHIBITORS, TRIAZEPINE COMPOUNDS, AND INTERMEDIATES THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP0934940A1

  公开（公告）日：1999-08-11

  The present invention relates to a cytokine production inhibitor comprising a compound of the formula [I] wherein R1 is aryl or heteroaryl; B is a group of the formula (a) or (b) wherein R2 is hydrogen atom, hydroxy, halogen atom and the like, R4 is hydrogen atom or halogen atom, or R2 and R4 in combination form carbonyl; R3 is lower alkoxy, cycloalkyl, aryl, heteroaryl, -X-Y and the like, wherein X is -(CH2)m-, -CO-, -COCH2-, -NHCH2-, -CH2NH-, -OCH2- and the like, Y is halogen atom, cycloalkyl, aryl or heteroaryl; R51 is -NHCONHR57 and the like; R52 is hydrogen atom or - COOR53; A is benzene ring or thiophene ring, novel triazepine compound and intermediates for the production of those triazepine compounds. The compounds of the formula [I] suppress production of cytokine such as IL-6, TNF-α, IL-8, IFNγ, IL-2, GM-CSF and the like, and are useful as cytokine production inhibitors or antiinflammatory drugs.

  本发明涉及一种细胞因子生产抑制剂，包括式[I]的化合物，其中R1为芳基或杂环基；B为式（a）或（b）的基团，其中R2为氢原子、羟基、卤原子等，R4为氢原子或卤原子，或R2和R4组成羰基；R3为较低的烷氧基、环烷基、芳基、杂环基、-X-Y等，其中X为-(CH2)m-、-CO-、-COCH2-、-NHCH2-、-CH2NH-、-OCH2-等，Y为卤原子、环烷基、芳基或杂环基；R51为-NHCONHR57等；R52为氢原子或-COOR53；A为苯环或噻吩环，以及用于生产这些三唑烷化合物的中间体。式[I]的化合物抑制细胞因子如IL-6、TNF-α、IL-8、IFNγ、IL-2、GM-CSF等的生产，可用作细胞因子生产抑制剂或抗炎药物。
• 6H-THIENO[2,3-E][1,2,4]TRIAZOLO[3,4-C][1,2,4]TRIAZEPINE DERIVATIVE
  申请人：AYUMI Pharmaceutical Corporation

  公开号：EP3640253A1

  公开（公告）日：2020-04-22

  The 6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,2,4]triazepine derivatives or salts thereof of the present invention have BRD4 inhibitory activity, and thus, they are useful as medicaments, in particular, as prophylaxis and/or therapeutic agents for diseases associated with BRD4.

  本发明的 6H-噻吩并[2,3-e][1,2,4]三唑并[3,4-c][1,2,4]三氮杂卓衍生物或其盐类具有 BRD4 抑制活性，因此可用作药物，特别是用作与 BRD4 相关疾病的预防和/或治疗药物。
• 6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,2,4]triazepine derivative
  申请人：AYUMI PHARMACEUTICAL CORPORATION

  公开号：US11186588B2

  公开（公告）日：2021-11-30

  The 6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,2,4]triazepine derivatives or salts thereof of the present invention have BRD4 inhibitory activity, and thus, they are useful as medicaments, in particular, as prophylaxis and/or therapeutic agents for diseases associated with BRD4.

  本发明的 6H-噻吩并[2,3-e][1,2,4]三唑并[3,4-c][1,2,4]三氮杂卓衍生物或其盐类具有 BRD4 抑制活性，因此可用作药物，特别是用作与 BRD4 相关疾病的预防和/或治疗药物。