(1R)-(+)-Camphor hydrazone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-(+)-Camphor hydrazone
• 英文别名: D-(+)-camphor hydrazone；D-(+)-(E)-camphor hydrazone；(+)-camphor hydrazone；(E)-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanylidene]hydrazine
• 化学式: C₁₀H₁₈N₂
• 分子量: 166.266
• InChiKey: PEGOJPQIBGLFFN-KSJHYXSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R)-(+)-Camphor hydrazone 在 正丁基锂 、 azidophosphonium bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以73%的产率得到2-diazocamphane
  参考文献：
  名称：

  正丁基锂和叠氮（二乙氨基）phosph将of转化为重氮化合物

  摘要：

  由与正丁基锂/己烷在-78°C下于THF反应制得的酰肼锂在约0°C下于THF中由叠氮基（二乙基氨基）efficiently有效，快速，安全地转化为相应的重氮化合物与三（二乙氨基）磷亚胺，氮和溴化锂。

  DOI：

  10.1016/s0040-4039(02)01443-0
• 作为产物：
  描述：

  白樟油 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以98%的产率得到(1R)-(+)-Camphor hydrazone
  参考文献：
  名称：

  d-(+)-樟脑基 N-酰基腙的合成及其抗病毒活性†

  摘要：

  介绍了一系列对牛痘和流感病毒具有抑制活性的新型D -(+)-樟脑N-酰基腙的设计和合成。已经开发了一种获得基于樟脑的N-酰基腙的简单途径，该途径在其结构中含有脂肪族、芳香族和杂环药效团支架。通过一整套光谱表征技术，包括二维核磁共振光谱、质谱和 X 射线衍射分析，对合成的腙的构象和构型进行了彻底的表征。对获得的化合物进行了针对牛痘病毒(VV)和流感H1N1病毒的体外活性筛选。结果表明，导出的N对于最有希望的化合物，-酰基腙表现出显着的抗病毒活性，对 VV 的选择性指数 > 280。

  DOI：

  10.1039/c8md00442k

文献信息

• New class of hantaan virus inhibitors based on conjugation of the isoindole fragment to (+)-camphor or (−)-fenchone hydrazonesv
  作者：Olga I. Yarovaya、Kseniya S. Kovaleva、Anna A. Zaykovskaya、Liudmila N. Yashina、Nadezda S. Scherbakova、Dmitry N. Scherbakov、Sophia S. Borisevich、Fedor I. Zubkov、Alexandra S. Antonova、Roman Yu. Peshkov、Ilia V. Eltsov、Oleg V. Pyankov、Rinat A. Maksyutov、Nariman F. Salakhutdinov

  DOI：10.1016/j.bmcl.2021.127926

  日期：2021.5

  This work presents the design and synthesis of camphor, fenchone, and norcamphor N-acylhydrazone derivatives as a new class of inhibitors of the Hantaan virus, which causes haemorrhagic fever with renal syndrome (HFRS). A cytopathic model was developed for testing chemotherapeutics against the Hantaan virus, strain 76–118. In addition, a study of the antiviral activity was carried out using a pseudoviral

  这项工作介绍了樟脑、茴香酮和去甲樟脑N-酰基腙衍生物的设计和合成，作为汉坦病毒的一类新抑制剂，汉坦病毒会导致肾综合征出血热 (HFRS)。开发了一种细胞病变模型，用于测试针对汉坦病毒 76-118 毒株的化疗药物。此外，使用假病毒系统进行了抗病毒活性的研究。发现命中化合物具有显着的活性 (IC 50  = 7.6 ± 2 µM) 以及低毒性 (CC 50  > 1000 µM)。使用分子对接程序，评估与汉坦病毒核蛋白的结合，并建立合成化合物的结构与抗病毒活性之间的相关性。
• Synthesis of<scp>d</scp>-(+)-camphor-based<i>N</i>-acylhydrazones and their antiviral activity
  作者：Kseniya S. Kovaleva、Fedor I. Zubkov、Nikolay I. Bormotov、Roman A. Novikov、Pavel V. Dorovatovskii、Victor N. Khrustalev、Yuriy V. Gatilov、Vladimir V. Zarubaev、Olga I. Yarovaya、Larisa N. Shishkina、Nariman F. Salakhutdinov

  DOI：10.1039/c8md00442k

  日期：——

  including 2D NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. In vitro screening for activity against vaccinia virus (VV) and influenza H1N1 virus was carried out for the obtained compounds. It was revealed that the derived N-acylhydrazones exhibited significant antiviral activity with a selectivity index >280 against VV for the most promising compound.

  介绍了一系列对牛痘和流感病毒具有抑制活性的新型D -(+)-樟脑N-酰基腙的设计和合成。已经开发了一种获得基于樟脑的N-酰基腙的简单途径，该途径在其结构中含有脂肪族、芳香族和杂环药效团支架。通过一整套光谱表征技术，包括二维核磁共振光谱、质谱和 X 射线衍射分析，对合成的腙的构象和构型进行了彻底的表征。对获得的化合物进行了针对牛痘病毒(VV)和流感H1N1病毒的体外活性筛选。结果表明，导出的N对于最有希望的化合物，-酰基腙表现出显着的抗病毒活性，对 VV 的选择性指数 > 280。
• Gream,G.E. et al., Australian Journal of Chemistry, 1974, vol. 27, p. 603 - 628
  作者：Gream,G.E. et al.

  DOI：——

  日期：——
• Preparation of α-diazines and α-2-pyridylazines containing (1R)-(+)-camphor or (1R)-(–)-fenchone residues and their complexes with Group 6 metal carbonyls
  作者：Bernard L. Shaw、Mark Thornton-Pett、Jonathan D. Vessey

  DOI：10.1039/dt9940003597

  日期：——

  New 2,3,6,7-tetraaza-1,3,5,7-octatetraene (alpha-diazine) derivatives camph=N-N=CH-CH=N-N=camph II where camph is a (1R)-(+)-camphor residue, C10H16, and fench=N-N=CH-CH=N-N=fench II, where fench is a 1R-(-)-fenchone residue. C10H16, have been obtained together with the 2'-pyridyl derivatives camph=N-N=CHC5H4N III and fench=N-N=CHC5H4N IV. The configurations around the four C=N bonds of I or II are E.E.E.E whilst those around the two azine C=N bonds in III and IV are E,E. Complexes of the types [M(CO)(4)L] (M = Cr, Mo or W; L = I-IV), [Mo(CO)(3)LL'] (L = I, L' = NCMe, PPh(3) or AsPh(3); L = II-IV, L' = PPh(3)), [Mo(CO)(2)L(PPh(3))(2)] (L = III or IV) and [Mo(CO)2Br (eta(3)-CH2C H=CH2) L] (L = I, III or IV) containing these azines as ligands have also been obtained. Complexes of II arethe most unstable and these together.with tetracarbonyl complexes-of IV appear to show restricted rotation around the N-N bond(s) caused by the steric requirements of the methyl groups on the fenchone residue(s). All the complexes have been characterised by multinuclear NMR (H-1, C-13 and P-31), IR and UV/VIS spectroscopies and mass spectrometry. The crystal structures of camph=N-N=CH-CH=N-N=camph I and fench=N-N=CH C5H4N IV have been determined.
• Conversions of hydrazones to diazo compounds by n-butyllithium and azidotris(diethylamino)phosphonium bromide
  作者：Mark McGuiness、Harold Shechter

  DOI：10.1016/s0040-4039(02)01443-0

  日期：2002.11

  Lithium hydrazonides, prepared by reactions of hydrazones with n-BuLi/hexane in THF at −78°C, are converted by azidotris(diethylamino)phosphonium bromide in THF at ∼0°C efficiently, rapidly, and safely to their corresponding diazo compounds along with tris(diethylamino)phosphorimine, nitrogen, and lithium bromide.

  由与正丁基锂/己烷在-78°C下于THF反应制得的酰肼锂在约0°C下于THF中由叠氮基（二乙基氨基）efficiently有效，快速，安全地转化为相应的重氮化合物与三（二乙氨基）磷亚胺，氮和溴化锂。