1,2-二氢-1-(金刚烷-1-基)-5H-四唑-5-硫酮 | 58473-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,2-二氢-1-(金刚烷-1-基)-5H-四唑-5-硫酮
• 英文名称: 1-((3s,5s,7s)-adamantan-1-yl)-1H-tetrazole-5-thiol
• 英文别名: 1-(adamantan-1-yl)-1H-tetrazole-5-thiol；1-(1-adamantyl)-2H-tetrazole-5-thione
• CAS: 58473-97-5
• 化学式: C₁₁H₁₆N₄S
• 分子量: 236.341
• InChiKey: IFZAAQJJFQHGIG-UHFFFAOYSA-N

物化性质

• 熔点：
  179-181℃ (isopropanol )

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.909
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-二氢-1-(金刚烷-1-基)-5H-四唑-5-硫酮 在 三乙胺 作用下， 以 乙腈 为溶剂， 以95%的产率得到1-(1-adamantyl)-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazole
  参考文献：
  名称：

  1-取代的5-[（3,5-二硝基苄基）硫烷基] -1 H-四唑及其等排类似物：一类新型的选择性抗结核药，对药物敏感和耐多药分枝杆菌有活性

  摘要：

  在这项工作中，描述了一类新型的高效抗结核药，即1-取代的5-[（3,5-二硝基苄基）硫烷基] -1 H-四唑及其氧杂和硒基类似物。最小抑菌浓度（MIC）值达到了1μM（0.36-0.44微克/毫升）对结核分枝杆菌CNCTC我八十八分之三百三十一和0.25-1μM针对六个多药耐药性临床分离菌株的结核分枝杆菌。这些化合物的抗分枝杆菌作用具有高度特异性，因为它们对所研究的所有八种细菌菌株和八种真菌菌株均无效。此外，这些化合物在四种哺乳动物细胞系中均表现出较低的体外毒性（IC 50 > 30μM）。我们还检查了化合物的结构-活性关系，特别是硝基基团的数量和位置，四唑和苄基部分之间的连接基以及四唑本身对抗分枝杆菌活性的影响。在不对分枝杆菌活性产生负面影响的情况下，四唑上取代基R 1的相对较高的变异性可进一步优化毒性，并进一步优化1-取代的5-[（3,5-二硝基苄基）硫烷基]-的ADME性质。 1 H-四唑化合物。

  DOI：

  10.1016/j.ejmech.2014.05.069
• 作为产物：
  描述：

  1-nitroxyadamantane 在 sodium azide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 10.0h， 生成 1,2-二氢-1-(金刚烷-1-基)-5H-四唑-5-硫酮
  参考文献：
  名称：

  笼式基质与硫亲核试剂的反应

  摘要：

  摘要 金刚烷系列的醇和硝酸金刚烷-1-基硝酸盐与硫亲核试剂在94％的硫酸中的反应提供了许多新的含硫金刚烷衍生物，如氨基甲硫醇盐，异硫氰酸盐和氨基脲二硫酸盐。通过将硝酸金刚烷-1-基与九水合硫化钠在94％的硫酸中反应合成二硫化金（金刚烷-1-基）。

  DOI：

  10.1134/s1070428021030052

文献信息

• Modified Julia–Kocienski Reagents for a Stereoselective Introduction of Trisubstituted Double Bonds: A Formal Total Synthesis of Limazepine E and Barmumycin
  作者：Guna Sakaine、Gints Smits

  DOI：10.1021/acs.joc.8b00643

  日期：2018.5.4

  A formal total synthesis of pyrrolo[1,4]benzodiazepine anticancer antibiotic family member limazepine E is described. The synthesis features a stereoselective introduction of a trisubstituted double bond using novel sterically demanding Julia–Kocienski reagents, allowing the number of linear steps to be significantly reduced. The potential of the newly developed reagents has also been demonstrated

  描述了吡咯并[1,4]苯并二氮杂anti抗癌抗生素家族成员利马西平E的正式全合成。该合成的特征是使用新颖的对空间要求苛刻的Julia-Kocienski试剂立体选择性地引入三取代双键，从而大大减少了线性步骤的数量。巴莫霉素的正式全合成也证明了新开发试剂的潜力。
• 5-((3-Bromoallyl)Sulfonyl)-1H-Tetrazoles for Bromodiene Synthesis
  作者：Shigeki Matsunaga、Takuro Suzuki、Seiya Fukagawa、Tatsuhiko Yoshino、Masahiro Anada

  DOI：10.3987/com-18-s(t)90

  日期：——

  Reagents for one-step construction of conjugated bromodienes from aldehydes are described. Various 1-alkyl- and 1-aryl-tetrazoyl bromoallylic sulfones were synthesized and evaluated in bromodiene synthesis. 1-Alkyl-tetrazoyl sulfones selectively afforded (1E,3Z)-bromodienes, while 1-aryl-tetrazoyl sulfones resulted in low selectivity.
• Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus
  作者：Vladimir V. Zarubaev、Efim L. Golod、Pavel M. Anfimov、Anna A. Shtro、Victor V. Saraev、Alexey S. Gavrilov、Alexander V. Logvinov、Oleg I. Kiselev

  DOI：10.1016/j.bmc.2009.11.047

  日期：2010.1

  Chemotherapy and chemoprophylaxis of influenza is one of the most important directions of health protection activity. Due to the high rate of drug-resistant strains of influenza virus, there is a need for the search and further development of new potent antivirals against influenza with a broad spectrum of activity. In the present study, a set of di-, tri- and tetrazole derivatives of adamantane was efficiently prepared and their anti-influenza activities evaluated against rimantadine-resistant strain A/Puerto Rico/8/34. In general, derivatives of tetrazole possessed the highest virus-inhibiting activity. We demonstrated that several compounds of this set exhibited much higher activity than the currently used antiviral rimantadine, a compound of related structure. Moreover, we showed that these azolo-adamantanes were significantly less toxic. This study demonstrates that influenza viruses can be inhibited by adamantylazoles and thus have potential for developing antiviral agents with an alternate mechanism of action. (C) 2009 Elsevier Ltd. All rights reserved.
• Adamantylazoles: XIII. Specificity of acid-catalyzed alkylation of 1-(1-adamantyl)-4,5-dihydro-1H-tetrazole-5-thione
  作者：A. V. Logvinov、I. N. Polyakova、E. L. Golod

  DOI：10.1134/s1070363209100247

  日期：2009.10

  In the reaction of 1-(1-adamantyl)-4,5-dihydro-1H-tetrazole-5-thione with 1-adamantyl in sulfuric acid 2-(1-adamantyl)-5-(1-adamantylsulfanyl)-2H-tetrazole and 1,3-bis(1-adamantyl)-5-(1-adamantylsulfanyl)-1H-tetrazolium salt are formed. Methylation of 1-(1-adamantyl)-4,5-dihydro-1H-tetrazole-5-thione in alkaline medium affords 1-(1-adamantyl)-5-methylsulfanyl-1H-tetrazole while its interaction with formaldehyde affoeds 1-(1-adamanttl)-4-(hydroxymethyl)-4,5-dihydro-1H-tetrazole-5-thione.
• Hrabalek; Kunes; Pour, Russian Journal of Organic Chemistry, <hi>2000</hi>, vol. 36, # 5, p. 761 - 762
  作者：Hrabalek、Kunes、Pour、Waisser

  DOI：——

  日期：——