(1-adamantan-1-ylethyl)butyl amine | 88313-73-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1-adamantan-1-ylethyl)butyl amine
• 英文别名: N-[1-(1-adamantyl)ethyl]butan-1-amine
• CAS: 88313-73-9
• 化学式: C₁₆H₂₉N
• mdl: MFCD11123300
• 分子量: 235.413
• InChiKey: YEQNLZLVXKPLFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-金刚烷甲酮 在 三氢化钐 、 碘 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 20.0h， 生成 (1-adamantan-1-ylethyl)butyl amine
  参考文献：
  名称：

  Banik; Ghatak; Samajdar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1134 - 1139

  摘要：

  DOI：

文献信息

• Titanium(IV) mediated reductive aminations of 1-adamantyl methyl ketone: facile preparation of potential antiviral agents rimantadine and its analogues
  作者：Sukanta Bhattacharyya

  DOI：10.1039/p19950001845

  日期：——

  A preparatively efficient, mild method for the synthesis of rimantadine and its analogues via novel reductive aminations of 1-adamantyl methyl ketone using titanium(IV) isopropoxide and sodium borohydride is reported.

  报道了一种使用异丙醇钛（IV）和硼氢化钠通过1-金刚烷基甲基酮的新型还原胺化反应合成金刚烷胺及其类似物的制备有效且温和的方法。
• Symmetric dimeric adamantanes for exploring the structure of two viroporins: influenza virus M2 and hepatitis C virus p7
  作者：Yasmine Magdy Mandour、Ulrike Breitinger、Chunlong Ma、Jun Wang、Frank Boeckler、Hans-Georg Breitinger、Darius Ziotos

  DOI：10.2147/dddt.s157104

  日期：——

  Background: Adamantane-based compounds have been identified to interfere with the ionchannel activity of viroporins and thereby inhibit viral infection. To better understand the difference in the inhibition mechanism of viroporins, we synthesized symmetric dimeric adamantane analogs of various alkyl-spacer lengths.Methods: Symmetric dimeric adamantane derivatives were synthesized where two amantadine or rimantadine molecules were linked by various alkyl-spacers. The inhibitory activity of the compounds was studied on two viroporins: the influenza virus M2 protein, expressed in Xenopus oocytes, using the two-electrode voltage-clamp technique, and the hepatitis C virus (HCV) p7 channels for five different genotypes (1a, 1b, 2a, 3a, and 4a) expressed in HEK293 cells using whole-cell patch-clamp recording techniques.Results: Upon testing on M2 protein, dimeric compounds showed significantly lower inhibitory activity relative to the monomeric amantadine. The lack of channel blockage of the dimeric amantadine and rimantadine analogs against M2 wild type and M2-S31N mutant was consistent with previously proposed drug-binding mechanisms and further confirmed that the pore-binding model is the pharmacologically relevant drug-binding model. On the other hand, these dimers showed similar potency to their respective monomeric analogs when tested on p7 protein in HCV genotypes 1a, 1b, and 4a while being 700-fold and 150-fold more potent than amantadine in genotypes 2a and 3a, respectively. An amino group appears to be important for inhibiting the ion-channel activity of p7 protein in genotype 2a, while its importance was minimal in all other genotypes.Conclusion: Symmetric dimeric adamantanes can be considered a prospective class of p7 inhibitors that are able to address the differences in adamantane sensitivity among the various genotypes of HCV.
• Banik; Zegrocka; Becker, Journal of Chemical Research - Part S, 2000, # 7, p. 321 - 323
  作者：Banik、Zegrocka、Becker

  DOI：——

  日期：——
• Kozlov, N. G.; Vyalimyae, T. K., Journal of general chemistry of the USSR, 1985, vol. 55, # 3, p. 539 - 542
  作者：Kozlov, N. G.、Vyalimyae, T. K.

  DOI：——

  日期：——
• Synthesis and antiviral activity of some derivatives of remantadine
  作者：I. Ya. Grava、Ya. Yu. Polis、M. Yu. Lidak、M. K. Indulen、N. A. Zamyatina

  DOI：10.1007/bf00765659

  日期：1980.10