7-Octylamino-5,6,7,8-tetrahydro-naphthalen-1-ol; hydrobromide | 81185-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 7-Octylamino-5,6,7,8-tetrahydro-naphthalen-1-ol; hydrobromide
• 英文别名: 7-(Octylamino)-5,6,7,8-tetrahydronaphthalen-1-ol;hydrobromide
• CAS: 81185-36-6
• 化学式: BrH*C₁₈H₂₉NO
• 分子量: 356.346
• InChiKey: MXCOTJFFMAGZRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  32.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (8-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-octyl-amine; hydrochloride 在 氢溴酸 作用下， 反应 3.0h， 生成 7-Octylamino-5,6,7,8-tetrahydro-naphthalen-1-ol; hydrobromide
  参考文献：
  名称：

  Synthesis and Antifungal Activities of Novel 2-Aminotetralin Derivatives

  摘要：

  Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoli ne ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14 alpha-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

  DOI：

  10.1021/jm0701167

文献信息

• 8-Hydroxy-2-(alkylamino)tetralins and related compounds as central 5-hydroxytryptamine receptor agonists
  作者：Lars Erik Arvidsson、Uli Hacksell、Anette Johansson、J. Lars G. Nilsson、Per Lindberg、Domingo Sanchez、Haakan Wikstroem、Kjell Svensson、Stephan Hjorth、Arvid Carlsson

  DOI：10.1021/jm00367a009

  日期：1984.1

  series of 2-(alkylamino)tetralins related to 8-hydroxy-2-(di-n-propylamino)tetralin (21) were prepared and tested as dopamine (DA) and 5-hydroxytryptamine (5-HT) receptor agonists. Several of the compounds were potent 5-HT agonists devoid of DA-mimetic effects. N-Ethyl or N-propyl substitution of 8-hydroxy-2-aminotetralin gave the most potent agonists. It was shown that the most potent compound, (+)-21

  制备了一系列与8-hydroxy-2-（di-n-丙基氨基）tetralin（21）相关的2-（烷基氨基）tetralins，并作为多巴胺（DA）和5-hydroxytryptamine（5-HT）受体激动剂进行了测试。这些化合物中有几种是有效的5-HT激动剂，没有DA模拟作用。8-羟基-2-氨基四氢萘的N-乙基或N-丙基取代产生最有效的激动剂。结果表明，最有效的化合物（+）-21具有2R构型。发现5,8-二甲氧基-2-（二正丙基氨基）四氢化萘（31）是一种弱的DA激动剂，没有5-HT活性。据报道，相应的茚满衍生物4,7-二甲氧基-2-（di-n-丙基氨基）茚满（39）对DA和5-HT受体均具有活性。
• Synthesis and Antifungal Activities of Novel 2-Aminotetralin Derivatives
  作者：Bin Yao、Haitao Ji、Yongbin Cao、Youjun Zhou、Jü Zhu、Jiaguo Lü、Yaowu Li、Jun Chen、Canhui Zheng、Yuanying Jiang、Rongmei Liang、Hui Tang

  DOI：10.1021/jm0701167

  日期：2007.11.1

  Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoli ne ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14 alpha-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.