Benzyl-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: Benzyl-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine
• 英文别名: N-benzyl-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: HAYFJPWCPAZXME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Benzyl-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以48%的产率得到8-甲氧基-1.2.3.4-四氢萘-2-胺
  参考文献：
  名称：

  Radioligand binding study of a series of 5-HT1A receptor agonists and definition of a steric model of this site

  摘要：

  DOI：

  10.1016/0223-5234(89)90160-8
• 作为产物：
  描述：

  1,7-二羟基萘 在 platinum(IV) oxide 盐酸 、 sodium hydroxide 、 乙醇 、 氢气 、 sodium 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 55.0 ℃ 、202.65 kPa 条件下， 反应 25.0h， 生成 Benzyl-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine
  参考文献：
  名称：

  2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents

  摘要：

  A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to compete for 2-[I-125]iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of [H-3]dopamine from rabbit retina. The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (K(i) = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor. The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows. First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor. We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.

  DOI：

  10.1021/jm00072a008

文献信息

• Therapeutically useful tetralin derivatives
  申请人：The Upjohn Company

  公开号：US05214156A1

  公开（公告）日：1993-05-25

  This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula ##STR1## wherein YR.sub.1 is OR.sub.1 at the 8 position where R.sub.1 is --CH.sub.2 --(C.sub.3-8 cycloalkyl); R.sub.2 is hydrogen or C.sub.1-3 alkyl; R.sub.3 is --CH.sub.2 --(C.sub.3-8 cycloalkyl); R.sub.4 is hydrogen, C.sub.1-8 alkyl, --CH.sub.2 --(C.sub.3-4 cycloalkyl), --(CH.sub.2).sub.m --R.sub.5 or --CH.sub.2 --CH.sub.2 --X--(CH.sub.2).sub.n CH.sub.3 ; n is zero to 3 and m is 2 or 3; X is oxygen or sulfur; R.sub.5 is phenyl, C.sub.1-3 alkoxy, C.sub.1-3 alkyl, 2-thiophene, 3-thiophene, or phenyl substituted with one or two substituent groups selected from chlorine, bromine or fluorine; and with the proviso that when R.sub.3 contains more than four carbon atoms and R.sub.4 is alkyl, said alkyl contains from 1 to 3 carbon atoms. Alternatively, --YR.sub.1 is --S--(C.sub.1-3 alkyl) at the 5, 6, 7 or 8 position of the aromatic ring or OR.sub.1 at the 8 position where R.sub.1 is selected from the group consisting of C.sub.1-8 alkyl, C.sub.2-8 alkenyl, --CH.sub.2 --(C.sub.3-8 cycloalkyl) or benzyl; R.sub.2 is hydrogen or (C.sub.1 -C.sub.3) alkyl; R.sub.3 is --CH.sub.2 --(C.sub.3 -C.sub.8) cycloalkyl; R.sub.4 is --(CH.sub.2).sub.m --(2-thiophenyl or 3-thiophenyl); and m is 2 or 3.

  该发明是具有治疗用途的四环烷类化合物及其药学上可接受的酸盐，其化学式为##STR1##其中YR.sub.1在8位处是OR.sub.1，其中R.sub.1是--CH.sub.2--（C.sub.3-8环烷基）; R.sub.2是氢或C.sub.1-3烷基; R.sub.3是--CH.sub.2--（C.sub.3-8环烷基）; R.sub.4是氢、C.sub.1-8烷基、--CH.sub.2--（C.sub.3-4环烷基）、--（CH.sub.2）.sub.m--R.sub.5或--CH.sub.2--CH.sub.2--X--（CH.sub.2）.sub.nCH.sub.3; n为0到3，m为2或3; X为氧或硫; R.sub.5为苯基、C.sub.1-3烷氧基、C.sub.1-3烷基、2-噻吩、3-噻吩或苯基，所述苯基被选自氯、溴或氟中的一种或两种取代基取代; 前提是当R.sub.3含有超过四个碳原子且R.sub.4为烷基时，所述烷基含有1到3个碳原子。或者，--YR.sub.1在芳香环的5、6、7或8位上是--S--（C.sub.1-3烷基）或OR.sub.1在8位处，其中R.sub.1选自C.sub.1-8烷基、C.sub.2-8烯基、--CH.sub.2--（C.sub.3-8环烷基）或苄基; R.sub.2是氢或（C.sub.1-C.sub.3）烷基; R.sub.3是--CH.sub.2--（C.sub.3-C.sub.8）环烷基; R.sub.4是--（CH.sub.2）.sub.m--（2-噻吩基或3-噻吩基）; m为2或3。
• Novel compounds for the treatment of migraine
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0450238A1

  公开（公告）日：1991-10-09

  This invention relates to novel 8-methoxy-2-amino-1,2,3,4-tetrahydronaphthalenes, to the methods for their preparation and to their use in the treatment of migraine and related disorders.

  本发明涉及新型的8-甲氧基-2-氨基-1,2,3,4-四氢萘烯，其制备方法以及它们在治疗偏头痛和相关疾病中的应用。
• Substituted 2-amidotetralins as melatonin agonists and antagonists
  申请人：NORTHWESTERN UNIVERSITY

  公开号：EP0420064A2

  公开（公告）日：1991-04-03

  The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as therapeutic and diagnostic reagents.

  本发明一般涉及具有褪黑激素受体活性的化合物，特别是取代的 2-脒基四氢萘衍生物；涉及包含这些化合物的药物制剂；以及涉及将这些化合物用作治疗和诊断试剂的方法。
• Procédé enzymatique pour la préparation de dérivés tétraliniques optiquement actifs
  申请人：SANOFI

  公开号：EP0683236A1

  公开（公告）日：1995-11-22

  La présente invention concerne un procédé enzymatique pour la préparation d'acides 2-tétrahydronaphtoïques optiquement actifs à partir des esters acémates correspondants par réaction avec une lipase.

  本发明涉及一种酶法工艺，通过与脂肪酶反应，从相应的醋酸酯制备光学活性 2-四氢萘酸。
• 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.