2-hydroxy-1-adamantanomethanol | 59182-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-1-adamantanomethanol
• 英文别名: 2-hydroxy-1-adamantane methanol；1-Hydroxymethyl-2-adamantanol；2-Hydroxy-1-adamantylmethanol；1-(Hydroxymethyl)adamantan-2-ol
• CAS: 59182-38-6
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: PUFOBDWCLXCAPH-UHFFFAOYSA-N

物化性质

• 沸点：
  331.8±10.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1-adamantanomethanol 在 chromium(VI) oxide 、 硫酸 作用下， 生成 1-Carbamoyladamantan-2-on
  参考文献：
  名称：

  Solvolysis of 1-substituted-2-adamantyl sulfonates. Bridging or no bridging?

  摘要：

  DOI：

  10.1021/ja00433a041
• 作为产物：
  描述：

  4-(epoxymethylene)protoadamantane 在 硫酸 作用下， 以 丙酮 为溶剂， 生成 2-hydroxy-1-adamantanomethanol
  参考文献：
  名称：

  Solvolysis of 1-substituted-2-adamantyl sulfonates. Bridging or no bridging?

  摘要：

  DOI：

  10.1021/ja00433a041

文献信息

• APOPTOSIS-INDUCED AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
  申请人：AbbVie Inc.

  公开号：US20130096120A1

  公开（公告）日：2013-04-18

  Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-xL proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bcl-xL protein.

  揭示了抑制抗凋亡Bcl-xL蛋白活性的化合物，含有这些化合物的组合物以及治疗在其中表达抗凋亡Bcl-xL蛋白的疾病的方法。
• Synthesis of 1,2-annulated adamantane heterocycles: structural determination studies of a bioactive cyclic sulfite
  作者：Grigoris Zoidis、Dimitra Benaki、Vassilios Myrianthopoulos、Lieve Naesens、Erik De Clercq、Emmanuel Mikros、Nicolas Kolocouris

  DOI：10.1016/j.tetlet.2009.03.132

  日期：2009.6

  The novel heterocycle 3-oxatetracyclo[5.3.1.15,9.02,5]dodecane 4 is prepared by a simple and effective method, involving synthesis of the corresponding 2-hydroxy-1-adamantanomethanol followed by its intramolecular cyclization with thionyl chloride, along with 4-oxo-adamantane-3,5,4-dioxathiane 5 in yields depending on the reaction temperature. Dioxathiane 5 was markedly active against vesicular stomatitis

  新颖的杂环3-氧杂四环[5.3.1.1 5,9 0.0 2,5 ]十二烷4是通过一个简单而有效的方法制备，涉及相应的2-羟基-1- adamantanomethanol的合成，随后其分子内环化与亚硫酰氯取决于反应温度，其产率与4-氧代金刚烷-3,5,4-二氧杂环丁烷5的产率有关。Dioxathiane 5对水疱性口炎病毒具有显着活性，其效力比（S）-9-（2,3-二羟丙基）腺嘌呤高2.5倍。NMR数据和有关亚硫酸盐5和相应的二恶烷6的理论计算表明，SO是赤道取向的。
• APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES
  申请人：AbbVie Inc.

  公开号：US20150072978A1

  公开（公告）日：2015-03-12

  Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-xL proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bcl-xL protein.

  本发明涉及抑制抗凋亡Bcl-xL蛋白活性的化合物、含有该化合物的组合物以及治疗表达抗凋亡Bcl-xL蛋白相关疾病的方法。
• Chakrabarti,J.K. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1893 - 1900
  作者：Chakrabarti,J.K. et al.

  DOI：——

  日期：——
• Anti-allodynic effect of 2-(aminomethyl)adamantane-1-carboxylic acid in a rat model of neuropathic pain: A mechanism dependent on CaV2.2 channel inhibition
  作者：Grigoris Zoidis、Alejandro Sandoval、Jorge Baruch Pineda-Farias、Vinicio Granados-Soto、Ricardo Felix

  DOI：10.1016/j.bmc.2014.02.006

  日期：2014.3

  Neuropathic pain is a serious physical disabling condition resulting from lesion or dysfunction of the peripheral sensory nervous system. Despite the fact that the mechanisms underlying neuropathic pain are poorly understood, the involvement of voltage-gated calcium (Ca-V) channels in its pathophysiology has justified the use of drugs that bind the Ca-V channel alpha(2)delta auxiliary subunit, such as gabapentin (GBP), to attain analgesic and anti-allodynic effects in models involving neuronal sensitization and nerve injury. GBP binding to alpha(2)delta inhibits nerve injury-induced trafficking of the alpha(1) pore forming subunits of Ca-V channels, particularly of the N-type, from the cytoplasm to the plasma membrane of pre-synaptic terminals in dorsal root ganglion neurons and dorsal horn spinal neurons. In the search for alternative forms of treatment, in this study we describe the synthesis and pharmacological profile of a GABA derivative, 2-aminoadamantane-1-carboxylic acid (GZ4), which displays a close structure-activity relationship with GBP. Behavioral assessment using von Frey filament stimuli showed that GZ4 treatment reverted mechanical allodynia/hyperalgesia in an animal model of spinal nerve ligation-induced neuropathic pain. In addition, using the patch clamp technique we show that GZ4 treatment significantly decreased whole-cell currents through N-type Ca-V channels heterologously expressed in HEK-293 cells. Interestingly, the behavioral and electrophysiological time course of GZ4 actions reflects that its mechanism of action is similar but not identical to that of GBP. While GBP actions require at least 24 h and imply uptake of the drug, which suggests that the drug acts mainly intracellularly affecting channels trafficking to the plasma membrane, the faster time course (1-3 h) of GZ4 effects suggests also a direct inhibition of Ca2+ currents acting on cell surface channels. (C) 2014 Elsevier Ltd. All rights reserved.