Homoadamantanonoxim | 26770-89-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Homoadamantanonoxim
• 英文别名: N-(4-tricyclo[4.3.1.13,8]undecanylidene)hydroxylamine
• CAS: 26770-89-8；26770-90-1；26775-81-5
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: ZHDRQJWVVAYIQP-UHFFFAOYSA-N

物化性质

• 沸点：
  310.4±11.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Homoadamantanonoxim 在 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(4-homoadamantyl)phthalimide
  参考文献：
  名称：

  Evaluation of Antiproliferative Effect of N-(alkyladamantyl)phthalimides In vitro

  摘要：

  A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.

  DOI：

  10.1111/j.1747-0285.2011.01305.x
• 作为产物：
  描述：

  三环[4.3.1.13,8]十一烷-4-酮 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 生成 Homoadamantanonoxim
  参考文献：
  名称：

  METHODS OF USE OF ANTIVIRAL COMPOUNDS

  摘要：

  本发明涉及部分与治疗、预防和抑制病毒性疾病的方法有关。在一个方面，本发明涉及抑制流感病毒（例如流感A病毒）的M2质子通道以及其他类似的病毒孔蛋白（例如埃博拉和马尔堡病毒的VP24；以及蓝舌病的NS3蛋白）。此外，本发明还涉及已被证明具有抗病毒活性的化合物，特别是抑制流感病毒的M2质子通道。

  公开号：

  US20110065762A1

文献信息

• METHODS OF USE OF ANTIVIRAL COMPOUNDS
  申请人：Wang Jizhou

  公开号：US20110065762A1

  公开（公告）日：2011-03-17

  The present invention relates, in part, to methods of treatment, prevention, and inhibition of viral disorders. In one aspect, the present invention relates to inhibition of the M2 proton channel of influenza viruses (e.g. influenza A virus) and other similar viroporins (e.g., VP24 of Ebola and Marburg viruses; and NS3 protein of Bluetongue). The present invention further relates, inter alia, to compounds which have been shown to possess antiviral activity, in particular, inhibiting the M2 proton channel of influenza viruses.

  本发明涉及部分与治疗、预防和抑制病毒性疾病的方法有关。在一个方面，本发明涉及抑制流感病毒（例如流感A病毒）的M2质子通道以及其他类似的病毒孔蛋白（例如埃博拉和马尔堡病毒的VP24；以及蓝舌病的NS3蛋白）。此外，本发明还涉及已被证明具有抗病毒活性的化合物，特别是抑制流感病毒的M2质子通道。
• Evaluation of Antiproliferative Effect of N-(alkyladamantyl)phthalimides In vitro
  作者：Margareta Horvat、Lidija Uzelac、Marko Marjanović、Nikola Cindro、Oliver Franković、Kata Mlinarić-Majerski、Marijeta Kralj、Nikola Basarić

  DOI：10.1111/j.1747-0285.2011.01305.x

  日期：2012.4

  A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.