2-(1-金刚烷)乙酰肼 | 19026-80-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(1-金刚烷)乙酰肼
• 中文别名: 金刚烷-1-基-乙酰肼；2-(1-金刚烷基)乙酰肼；2-(1-金刚烷基)乙烷肼
• 英文名称: 1-tricyclo[3.3.1.1^3,7]decaneacetohydrazide
• 英文别名: 2-[4-(tricyclo[3.3.1.1^3,7]dec-1-yl)phenyl]acetohydrazide；Adamantan-1-acetohydrazid；Adamantyl-1-acetohydrazid；2-(1-Adamantyl)acetohydrazide
• CAS: 19026-80-3
• 化学式: C₁₂H₂₀N₂O
• mdl: MFCD00185799
• 分子量: 208.304
• InChiKey: ZORPHDZMMHDLAM-UHFFFAOYSA-N

物化性质

• 沸点：
  389.0±11.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.916
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  5-硝基糠醛 、 2-(1-金刚烷)乙酰肼 以 乙醇 为溶剂， 反应 12.0h， 以78%的产率得到N²-(5-nitro-2-furanmethylene)-1-tricyclo[3.3.1.1^3,7]decanoacetohydrazide
  参考文献：
  名称：

  5-硝基-2-呋喃甲醛与金刚烷烷酰肼的新：合成和体外锥虫活性† ‡

  摘要：

  Nifurtimox是5-硝基-2-呋喃甲醛的，可用于治疗布鲁氏锥虫和克氏锥虫感染。利用我们先前的观察，金刚烷衍生物显示出锥虫杀虫活性，我们设计并合成了一系列5-硝基-2-呋喃with与金刚烷烷酰肼。最有前途的化合物具有大于20倍的活性（IC 50比尼呋替莫斯约100 nM），选择性指数为20-80。SAR研究表明，活性与亲脂性增加有关，并受构象柔韧性影响。缺乏硝基的衍生物实际上对两种寄生虫均无活性。所描述的方法证明了增强具有已知锥虫杀灭活性的化学实体效力的可行性。

  DOI：

  10.1039/c6md00035e
• 作为产物：
  描述：

  1-金刚烷乙酸 生成 2-(1-金刚烷)乙酰肼
  参考文献：
  名称：

  Synthesis of Adamantane Derivatives. II. Preparation of Some Derivatives from Adamantylacetic Acid

  摘要：

  DOI：

  10.1246/bcsj.41.238

文献信息

• Synthesis and Evaluation of Nifurtimox–Adamantane Adducts with Trypanocidal Activity
  作者：Angeliki‐Sofia Foscolos、Ioannis Papanastasiou、Andrew Tsotinis、Martin C. Taylor、John M. Kelly

  DOI：10.1002/cmdc.201900165

  日期：2019.7.3

  The synthesis and pharmacological evaluation of C1‐substituted adamantane hydrazones, their C2‐substituted isomers, and C1‐substituted adamantane furanoic carboxamides is described. These new adamantane derivatives exhibited an interesting pharmacological profile in terms of trypanocidal activity and selectivity. The most active adduct with the best selectivity in this study was found to be the phenylacetoxy

  描述了C1取代的金刚烷，它们的C2取代的异构体以及C1取代的金刚烷呋喃甲酸羧酰胺的合成和药理学评价。这些新的金刚烷衍生物在锥虫杀伤活性和选择性方面表现出有趣的药理作用。在这项研究中，活性最高，选择性最佳的加合物是苯乙酰氧基1 b（2- [4-（三环[3.3.1.1 3,7 ] dec-1-基）苯基] -N' -[（ 5-硝基呋喃-2-基）亚甲基]乙酰肼; EC 50 = 11±0.9 n m，SI Tb = 770）。
• 11-Beta-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia
  申请人：Balkovec M. James

  公开号：US20050070720A1

  公开（公告）日：2005-03-31

  Compounds having Formula (I), including pharmaceutically acceptable salts and prodrugs thereof: are selective inhibitors of the 11β-HSD1 enzyme. They inhibit the 11β-HSD1-mediated conversion of cortisone and other 11-keto-glucocorticoids to cortisol and other 11β-hydroxy-glucocorticoids. The 11β-HSD1 inhibitors therefore decrease the amount of cortisol in target tissues, thereby modulating the effects of cortisol. Modulation of cortisol may be effective in controlling non-insulin-dependent diabetes (NIDDM), hyperglycemia, obesity, insulin resistance, dyslipidemia, hyperlipidemia, hypertension, Syndrome X, and other symptoms associated with NIDDM or with excess cortisol in the body.

  化合物公式为（I）的化合物，包括其药学上可接受的盐和前药：是11β-HSD1酶的选择性抑制剂。它们抑制11β-HSD1介导的可的松和其他11-酮基-糖皮质激素转化为皮质醇和其他11β-羟基-糖皮质激素的过程。因此，11β-HSD1抑制剂减少了目标组织中皮质醇的含量，从而调节了皮质醇的效应。调节皮质醇可能对控制非胰岛素依赖性糖尿病（NIDDM）、高血糖、肥胖症、胰岛素抵抗、血脂异常、高脂血症、高血压、X综合征和与体内过多皮质醇有关的其他症状有效。
• 2-Adamantyl hydrazines and pharmaceutical compositions containing them
  申请人：Teva Pharmaceutical Industries Limited

  公开号：EP0002066A1

  公开（公告）日：1979-05-30

  The invention provides novel 2-adamantyl hydrazine derivatives of the general formula A In this formula R, is hydrogen or a lower alkyl group of 1-4 carbon atoms; R2 and R3 are the same or different and are each hydrogen, an unsubstituted or substituted radical being a lower alkyl of 1-4 carbon atoms, a lower alkanoic acid radical of 2-4 carbon atoms or a lower alkyl ester thereof, adamantyl, aryl, aralkyl, in which the alkyl moiety has from 1-4 carbon atoms or an unsubstituted or substituted heterocyclic radical of aromatic character; or R2 and R3 together with the nitrogen atom to which they are attached form an unsubstituted or substituted non-aromatic cyclic radical. The invention further provides pharmaceutically acceptable acid addition salts of the above compounds. Several methods of preparation of the new compounds are described. The novel compounds according to the invention possess valuable antifungal (human and plant), antiviral, antiprotozoal and antimicrobial properties.

  本发明提供了通式 A 的新型 2-金刚烷基肼衍生物 在该式中，R为氢或1-4个碳原子的低级烷基；R2和R3相同或不同，各自为氢、未取代或取代的1-4个碳原子的低级烷基、2-4个碳原子的低级烷酸基或其低级烷基酯、金刚烷基、芳基、芳烷基（其中烷基具有1-4个碳原子）或未取代或取代的芳香杂环基；或 R2 和 R3 与它们所连接的氮原子一起形成未取代或取代的非芳香环基。 本发明进一步提供了上述化合物的药学上可接受的酸加成盐。 本发明描述了几种新化合物的制备方法。 本发明的新型化合物具有宝贵的抗真菌（人类和植物）、抗病毒、抗原虫和抗微生物特性。
• Adamantyl triazoles as selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1
  作者：Steven Olson、Susan D. Aster、Kai Brown、Linda Carbin、Donald W. Graham、Anne Hermanowski-Vosatka、Cheryl B. LeGrand、Steven S. Mundt、Michael A. Robbins、James M. Schaeffer、Llnon H. Slossberg、Michael J. Szymonifka、Rolf Thieringer、Samuel D. Wright、James M. Balkovec

  DOI：10.1016/j.bmcl.2005.06.040

  日期：2005.10

  Adamantyl triazoles were identified as selective inhibitors of 11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1). They are active both in in vitro and in in vivo pharmacodynamic models. The synthesis and structure-activity relationships of these inhibitors are presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Statistical molecular design of a focused salicylidene acylhydrazide library and multivariate QSAR of inhibition of type III secretion in the Gram-negative bacterium Yersinia
  作者：Markus K. Dahlgren、Caroline E. Zetterström、Åsa Gylfe、Anna Linusson、Mikael Elofsson

  DOI：10.1016/j.bmc.2010.02.022

  日期：2010.4

  A combined application of statistical molecular design (SMD), quantitative structure-activity relationship (QSAR) modeling and prediction of new active compounds was effectively used to develop salicylidene acylhydrazides as inhibitors of type III secretion (T3S) in the Gram-negative pathogen Yersinia pseudotuberculosis. SMD and subsequent synthesis furnished 50 salicylidene acylhydrazides in high purity. Based on data from biological evaluation in T3S linked assays 18 compounds were classified as active and 25 compounds showed a dose-dependent inhibition. The 25 compounds were used to compute two multivariate QSAR models and two multivariate discriminant analysis models were computed from both active and inactive compounds. Three of the models were used to predict 4416 virtual compounds in consensus and eight new compounds were selected as an external test set. Synthesis and biological evaluation of the test set in Y. pseudotuberculosis and the intracellular pathogen Chlamydia trachomatis validated the models. Y. pseudotuberculosis and C. trachomatis cell-based infection models showed that compounds identified in this study are selective and non-toxic inhibitors of T3S dependent virulence. (C) 2010 Elsevier Ltd. All rights reserved.