(Z)-1-Naphthylacetamidoxim | 925252-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-Naphthylacetamidoxim
• 英文别名: 1-naphthyl-acetamidoxime；N'-hydroxy-2-naphthalen-1-ylethanimidamide
• CAS: 925252-83-1
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: NWWCOKUDFCFADE-UHFFFAOYSA-N

物化性质

• 熔点：
  108-111
• 沸点：
  385.8±35.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  15.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 储存条件：
  存储条件：2-8°C，干燥且密封。

反应信息

• 作为反应物：
  描述：

  (Z)-1-Naphthylacetamidoxim 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 Phosphoric acid mono-(4-{(S)-2-acetylamino-2-[(S)-3-carbamoyl-1-(3-naphthalen-1-ylmethyl-[1,2,4]oxadiazol-5-yl)-propylcarbamoyl]-ethyl}-phenyl) ester
  参考文献：
  名称：

  Discovery of Potent and Selective SH2 Inhibitors of the Tyrosine Kinase ZAP-70

  摘要：

  A series of 1,2,4-oxadiazole analogues has been shown to be potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70, a potential therapeutic target for immune suppression. These compounds typically are 200-400-fold more potent than the native, monophosphorylated tetrapeptide sequences. When compared with the high-affinity xi-1-ITAM peptide (Ac-NQL-pYNELNLGRREE-pYDVLD-NH2, wherein pY refers to phosphotyrosine) some of the best 1,2,4-oxadiazole analogues are approximately 1 order of magnitude less active. This series of compounds displays an unprecedented level of selectivity over the closely related tyrosine kinase Syk, as well as other SH2-containing proteins such as Src and Grb2. Gel shift studies using a protein construct consisting only of C-terminal ZAP-70 SH2 demonstrate that these compounds can effectively engage this particular SH2 domain.

  DOI：

  10.1021/jm990229t
• 作为产物：
  描述：

  1-萘乙腈 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以42%的产率得到(Z)-1-Naphthylacetamidoxim
  参考文献：
  名称：

  Lessel; Herfs, Pharmazie, 2000, vol. 55, # 1, p. 22 - 26

  摘要：

  DOI：

文献信息

• New O-(3-amino-2-hydroxy-propyl)-amidoxime derivatives, process for the
  申请人：Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.

  公开号：US04187220A1

  公开（公告）日：1980-02-05

  A compound effective in the treatment of diabetic angiopathy, i.e. a selective .beta.-receptor blocker has the formula ##STR1## wherein: R.sup.2 is a hydrogen or alkyl having one to five carbon atoms, R.sup.3 is alkyl having one to five carbon atoms, cycloalkyl or phenyl optionally substituted with hydroxyl or phenyl, or R.sup.2 and R.sup.3 together form a five- to eight-membered ring optionally containing also other heteroatoms and/or fused with an other ring, preferably phenyl, naphthyl, quinolyl, isoquinolyl, pyridyl, pyrazolyl, R.sup.5 is hydrogen or alkyl having one to four carbon atoms, cycloalkyl or phenyl optionally substituted with halogen, alkoxy having one to four carbon atoms or alkyl having one to four carbon atoms, R.sup.6 is hydrogen, alkyl having one to four carbon atoms or phenyl, m=0, 1 or 2, and n=0, 1 or 2.

  一种用于治疗糖尿病血管病的复合物，即一种选择性β受体阻滞剂，其化学式为##STR1##其中：R.sup.2是氢或具有一到五个碳原子的烷基，R.sup.3是具有一到五个碳原子的烷基，环烷基或苯基，可选择性地用羟基或苯基取代，或者R.sup.2和R.sup.3共同形成一个五到八元环，也可以含有其他杂原子和/或与其他环融合，优选苯基，萘基，喹啉基，异喹啉基，吡啶基，吡唑基，R.sup.5是氢或具有一到四个碳原子的烷基，环烷基或苯基，可选择性地用卤素，具有一到四个碳原子的烷氧基或烷基取代，R.sup.6是氢，具有一到四个碳原子的烷基或苯基，m=0，1或2，n=0，1或2。
• Synthesis and evaluation of 1,2,4-oxadiazole derivatives as potential anti-inflammatory agents by inhibiting NF-κB signaling pathway in LPS-stimulated RAW 264.7 cells
  作者：Yu-Ying Zhang、Qian-Qian Zhang、Juan Zhang、Jia-Li Song、Jia-Cheng Li、Ke Han、Jin-Tian Huang、Cheng-Shi Jiang、Hua Zhang

  DOI：10.1016/j.bmcl.2020.127373

  日期：2020.9

  In this study, a series of compounds with 1,2,4-oxadiazole core was designed and synthesized for the optimi-zation of JC01, an anti-inflammatory hit identified from our in-house compound library using NF-xB pathway luciferase assay and NO production assay. All the synthetic compounds 1-29 have been screened for their anti-inflammatory effects by evaluating their inhibition against LPS-induced NO release, and compound 17 exhibited the highest activity. Western blotting and immunofluorescence analysis revealed that 17 prominently inhibited LPS-induced activation of NF-kappa B in RAW264.7 cells and blocked the phosphorylation of p65. Consistent with these results, it was found that 17 prevented the nuclear translocation of NF-kappa B induced by LPS. These data highlighted 17 as a promising anti-inflammatory agent by inhibiting NF-kappa B activity.
• US4187220A
  申请人：——

  公开号：US4187220A

  公开（公告）日：1980-02-05
• US4308399A
  申请人：——

  公开号：US4308399A

  公开（公告）日：1981-12-29
• Discovery of Potent and Selective SH2 Inhibitors of the Tyrosine Kinase ZAP-70
  作者：Chi B. Vu、Evelyn G. Corpuz、Taylor J. Merry、Selvaluxmi G. Pradeepan、Catherine Bartlett、Regine S. Bohacek、Martyn C. Botfield、Charles J. Eyermann、Berkley A. Lynch、Ian A. MacNeil、Mary K. Ram、Marie Rose van Schravendijk、Shelia Violette、Tomi K. Sawyer

  DOI：10.1021/jm990229t

  日期：1999.10.1

  A series of 1,2,4-oxadiazole analogues has been shown to be potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70, a potential therapeutic target for immune suppression. These compounds typically are 200-400-fold more potent than the native, monophosphorylated tetrapeptide sequences. When compared with the high-affinity xi-1-ITAM peptide (Ac-NQL-pYNELNLGRREE-pYDVLD-NH2, wherein pY refers to phosphotyrosine) some of the best 1,2,4-oxadiazole analogues are approximately 1 order of magnitude less active. This series of compounds displays an unprecedented level of selectivity over the closely related tyrosine kinase Syk, as well as other SH2-containing proteins such as Src and Grb2. Gel shift studies using a protein construct consisting only of C-terminal ZAP-70 SH2 demonstrate that these compounds can effectively engage this particular SH2 domain.