ethyl 2-nitro-2-adamantanepropanoate | 158832-99-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-nitro-2-adamantanepropanoate
• 英文别名: Ethyl 3-(2-nitro-2-adamantyl)propanoate
• CAS: 158832-99-6
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: XYGXGAVMTBDPLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-nitro-2-adamantanepropanoate 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 24.75h， 生成 2-(3-chloropropyl)-2-nitrotricyclo[3.3.1.1^3,7]decane
  参考文献：
  名称：

  Synthesis and Antiviral Activity Evaluation of Some New Aminoadamantane Derivatives. 2

  摘要：

  The synthesis of some new aminoadamantane derivatives is described. The new compounds were evaluated against a wide range of viruses [influenza A H1N1, influenza A H2N2, influenza A H3N2, influenza B, parainfluenza 3, herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), thymidine kinase-deficient (TK-) HSV-1, vaccinia, vesicular stomatitis, polio 1, Coxsackie B4, Sindbis, Semliki forest, Reo 1, varicella-zoster virus (VZV), TK- VZV, human cytomegalo-virus (HCMV),,and human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2)]. Some of them proved markedly active against the influenza A H2N2 (compounds 4a,b, 5a, 6a, and 7a), H3N2 (compounds 5a, 6a, and 7a), and H1N1 (compounds 4b,c and 6d). Since compounds 5a, 6a, and 7a, amantadine, and rimantadine showed the same comparative pattern of potency against influenza strains H2N2, H3N2, and B, it may postulated that they act according to a similar mechanism, with regard to their ''amine'' effect, on the M2 ion channel of influenza A (H1N1, H2N2, or H3N2). In general, no significant activity was noted with any of the new compounds against any of the other viruses tested, making their activity against influenza virus more specific and striking. Borderline activity was noted with some of the compounds (4b,c, 5a-c, and 8a) against HIV-1.

  DOI：

  10.1021/jm950891z
• 作为产物：
  描述：

  2-Adamantanone oxime 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 硝酸 、 苄基三甲基氢氧化铵 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 Petroleum ether 、 叔丁醇 为溶剂， 反应 2.33h， 生成 ethyl 2-nitro-2-adamantanepropanoate
  参考文献：
  名称：

  一些氨基金刚烷衍生物的合成和抗病毒活性评估。

  摘要：

  描述了一些螺[环丙烷-1，2'-金刚烷] -2-胺和甲胺和一些螺[吡咯烷-2,2'-金刚烷]的合成。对标题化合物进行了广泛的病毒评估（甲型流感，乙型流感，副流感3，RSV，HSV-1，TK-HSV-1，HSV-2，牛痘，水疱性口炎，脊髓灰质炎1，柯萨奇B4，辛德比斯， semliki森林，Reo 1，HIV-1和HIV-2）以及其中一些（化合物6b，6c，9a，16a，16b和17）以明显低于其浓度的浓度抑制了甲型流感病毒的细胞病变。金刚烷胺也明显低于证明对宿主细胞有细胞毒性的浓度。新的氨基金刚烷衍生物都没有抗乙型流感病毒或任何其他测试病毒的活性，这表明它们作为抗甲型流感病毒的特异性。

  DOI：

  10.1021/jm00044a010

文献信息

• Kolocouris Nicolas, Foscolos George B., Kolocouris Antonios, Marakos Pana+, J. Med. Chem, 37 (1994) N 18, S 2896-2902
  作者：Kolocouris Nicolas, Foscolos George B., Kolocouris Antonios, Marakos Pana+

  DOI：——

  日期：——
• Synthesis and Antiviral Activity Evaluation of Some New Aminoadamantane Derivatives. 2
  作者：Nicolas Kolocouris、Antonios Kolocouris、George B. Foscolos、George Fytas、Johan Neyts、Elisabeth Padalko、Jan Balzarini、Robert Snoeck、Graciela Andrei、Erik De Clercq

  DOI：10.1021/jm950891z

  日期：1996.1.1

  The synthesis of some new aminoadamantane derivatives is described. The new compounds were evaluated against a wide range of viruses [influenza A H1N1, influenza A H2N2, influenza A H3N2, influenza B, parainfluenza 3, herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), thymidine kinase-deficient (TK-) HSV-1, vaccinia, vesicular stomatitis, polio 1, Coxsackie B4, Sindbis, Semliki forest, Reo 1, varicella-zoster virus (VZV), TK- VZV, human cytomegalo-virus (HCMV),,and human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2)]. Some of them proved markedly active against the influenza A H2N2 (compounds 4a,b, 5a, 6a, and 7a), H3N2 (compounds 5a, 6a, and 7a), and H1N1 (compounds 4b,c and 6d). Since compounds 5a, 6a, and 7a, amantadine, and rimantadine showed the same comparative pattern of potency against influenza strains H2N2, H3N2, and B, it may postulated that they act according to a similar mechanism, with regard to their ''amine'' effect, on the M2 ion channel of influenza A (H1N1, H2N2, or H3N2). In general, no significant activity was noted with any of the new compounds against any of the other viruses tested, making their activity against influenza virus more specific and striking. Borderline activity was noted with some of the compounds (4b,c, 5a-c, and 8a) against HIV-1.
• Synthesis and Antiviral Activity Evaluation of Some Aminoadamantane Derivatives
  作者：Nicolas Kolocouris、George B. Foscolos、Antonios Kolocouris、Panayotis Marakos、Nicole Pouli、George Fytas、Satoru Ikeda、Erik De Clercq

  DOI：10.1021/jm00044a010

  日期：1994.9

  The synthesis of some spiro[cyclopropane-1,2'-adamantan]-2-amines and methanamines and some spiro[pyrrolidine-2,2'-adamantanes] is described. The title compounds were evaluated against a wide range of viruses (influenza A, influenza B, parainfluenza 3, RSV, HSV-1, TK- HSV-1, HSV-2, vaccinia, vesicular stomatitis, polio 1, coxsackie B4, sindbis, semliki forest, Reo 1, HIV-1, and HIV-2), and some of them

  描述了一些螺[环丙烷-1，2'-金刚烷] -2-胺和甲胺和一些螺[吡咯烷-2,2'-金刚烷]的合成。对标题化合物进行了广泛的病毒评估（甲型流感，乙型流感，副流感3，RSV，HSV-1，TK-HSV-1，HSV-2，牛痘，水疱性口炎，脊髓灰质炎1，柯萨奇B4，辛德比斯， semliki森林，Reo 1，HIV-1和HIV-2）以及其中一些（化合物6b，6c，9a，16a，16b和17）以明显低于其浓度的浓度抑制了甲型流感病毒的细胞病变。金刚烷胺也明显低于证明对宿主细胞有细胞毒性的浓度。新的氨基金刚烷衍生物都没有抗乙型流感病毒或任何其他测试病毒的活性，这表明它们作为抗甲型流感病毒的特异性。