1-cyano-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene | 97352-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-cyano-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: 1-cyano-5,6-dimethoxytetralin；1-Cyano-5,6-dimethoxy-(1,2,3,4-tetrahydronaphthalene)；5,6-Dimethoxy-1,2,3,4-tetrahydro-1-naphthalenecarbonitrile；5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-carbonitrile
• CAS: 97352-15-3
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: ZLXZKBRPXNTGHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyano-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene 在 platinum(IV) oxide 、 镍 ammonium hydroxide 、 氢气 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 8.5h， 生成 1-<(N-isopropylamino)methyl>-5,6-dimethoxytetralin hydrochloride
  参考文献：
  名称：

  构象定义的肾上腺素能药物。1.新型α2选择性肾上腺素能药物的设计和合成：基于静电排斥的构象原型。

  摘要：

  先前关于2-和6-氟去甲肾上腺素的肾上腺素选择性的报道促使我们提出一个假设，该假设基于由芳族氟原子和侧链羟基之间的静电排斥引起的构象偏爱来解释这种选择性。制备了一系列氮取代的邻苯二酚（氨基甲基）苯并环丁烯，茚满，四氢化萘和苯并环庚烯，并确定了它们的放射性配体结合亲和力时，发现结合亲和力结果的整体模式支持静电排斥假设。放射性配体结合测定还揭示了这些化合物中几种高度α2选择性肾上腺素能药物，

  DOI：

  10.1021/jm00148a005
• 作为产物：
  描述：

  5,6-二甲氧基-1,2,3,4-四氢1-萘酮 在 盐酸 、 sodium tetrahydroborate 、 三氯化铝 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.0h， 生成 1-cyano-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  构象定义的肾上腺素能药物。2.儿茶酚咪唑啉衍生物：对α1和α2肾上腺素能受体的生物作用。

  摘要：

  描述了非常有效的α-肾上腺素能激动剂2-（5,6-二羟基-1,2,3,4-四氢-1-萘基）咪唑啉（A-54741，4）的合成和药理作用。提出了由于碳环尺寸从4个变化到七个（2-5）从4个变化而引起的生物活性变化，并给出了解释这种活性变化的解释，其中考虑了它们的“拟合精确性” α1和α2肾上腺素受体的化合物。在体外发现化合物4是一种完全激动剂，对α2受体（ED50去甲肾上腺素（NE）/ ED50 4 = 188 +/- 22）的效力比对α1受体（ED50 NE / ED50 4 = 13 + /-2）。

  DOI：

  10.1021/jm00154a006

文献信息

• Conformationally defined adrenergic agents. 2. Catechol imidazoline derivatives: biological effects at .alpha.1 and .alpha.2 adrenergic receptors
  作者：John F. DeBernardis、John J. Kyncl、Fatima Z. Basha、David L. Arendsen、Yvonne C. Martin、Martin Winn、Daniel J. Kerkman

  DOI：10.1021/jm00154a006

  日期：1986.4

  The synthesis and pharmacology of 2-(5,6-dihydroxy-1,2,3,4-tetrahydro-1-naphthyl)imidazoline (A-54741, 4), a very potent alpha-adrenergic agonist, are described. The change in biological activity resulting from variation of the carbocyclic ring size of 4 from four through seven members (2-5) is presented, as well as an explanation that accounts for this change in activity by considering the "exactness

  描述了非常有效的α-肾上腺素能激动剂2-（5,6-二羟基-1,2,3,4-四氢-1-萘基）咪唑啉（A-54741，4）的合成和药理作用。提出了由于碳环尺寸从4个变化到七个（2-5）从4个变化而引起的生物活性变化，并给出了解释这种活性变化的解释，其中考虑了它们的“拟合精确性” α1和α2肾上腺素受体的化合物。在体外发现化合物4是一种完全激动剂，对α2受体（ED50去甲肾上腺素（NE）/ ED50 4 = 188 +/- 22）的效力比对α1受体（ED50 NE / ED50 4 = 13 + /-2）。
• Adrenergic amidines
  申请人：Abbott Laboratories

  公开号：US04634705A1

  公开（公告）日：1987-01-06

  Disclosed herein are adrenergic compounds represented by the formula ##STR1## wherein m is 0, 1 or 2; R.sub.1, R.sub.2, R.sub.3 and R.sub.7 are taken from the group consisting of hydrogen, hydroxy, loweralkyl, loweralkoxy, halo, amino, acetamido or NHSO.sub.2 R wherein R is taken from the group consisting of hydrogen or loweralkyl, provided that R.sub.1, R.sub.2, R.sub.3 and R.sub.7 cannot simultaneously be hydrogen or halo, and provided that when one of R.sub.1, R.sub.2, R.sub.3 and R.sub.7 is halo, the others cannot simultaneously be hydrogen and when two of R.sub.1, R.sub.2, R.sub.3 and R.sub.7 are halo, the other two cannot simultaneously be hydrogen and provided that R.sub.1 and R.sub.7 cannot simultaneously be methoxy each when R.sub.2 and R.sub.3 are hydrogen; R.sub.1 and R.sub.2 or R.sub.2 and R.sub.3 or R.sub.3 and R.sub.7 taken together can form a methylenedioxy or ethylenedioxy bridge; or R.sub.1 and R.sub.2 or R.sub.2 and R.sub.3 or R.sub.3 and R.sub.7 taken together with the aromatic ring can form a benzimidazole or indole bridge; and R.sub.4 and R.sub.5 are hydrogen or taken together form a closed ring of the formula ##STR2## wherein n is 1 or 2, and the combined solid and dashed line represents a single or double bond when n is 1, and R.sub.6 is taken from the group consisting of hydrogen or loweralkyl, and the pharmaceutically acceptable salts thereof.

  本公开涉及的肾上腺素类化合物由以下式表示：其中m为0、1或2；R.sub.1、R.sub.2、R.sub.3和R.sub.7取自氢、羟基、较低烷基、较低烷氧基、卤素、氨基、乙酰胺基或NHSO.sub.2 R的群，其中R取自氢或较低烷基，但要求R.sub.1、R.sub.2、R.sub.3和R.sub.7不能同时为氢或卤素，且当R.sub.1、R.sub.2、R.sub.3和R.sub.7中的一个为卤素时，其他的不能同时为氢，当R.sub.1、R.sub.2、R.sub.3和R.sub.7中有两个为卤素时，其他两个不能同时为氢，而且当R.sub.1和R.sub.7同时为甲氧基时，R.sub.2和R.sub.3为氢；R.sub.1和R.sub.2或R.sub.2和R.sub.3或R.sub.3和R.sub.7结合在一起可以形成甲二氧基或乙二氧基桥；或者R.sub.1和R.sub.2或R.sub.2和R.sub.3或R.sub.3和R.sub.7与芳香环结合在一起可以形成苯并咪唑或吲哚桥；R.sub.4和R.sub.5为氢或结合在一起形成下式的闭环：其中n为1或2，组合的实线和虚线代表单键或双键，当n为1时，R.sub.6取自氢或较低烷基，以及其药用可接受的盐。
• Spirotetrahydronaphthalene analogues of sympathomimetic catecholamines. Synthesis and adrenergic activity of 5,6- and 6,7-dihydroxy-3,4-dihydrospiro[naphthalen-1(2<i>H</i>)-3′ -piperidines]
  作者：Bruno Macchia、Clementina Manera、Adriano Martinelli、Susanna Nencetti、Elisabetta Orlandini、Maria Cristina Breschi、Claudia Martini、Enrica Martinotti

  DOI：10.1211/0022357021778961

  日期：2010.2.18

  The 5,6- (5a) and 6,7-dihydroxy-3,4-dihydrospiro[naphthalen-1 (2H)-3'-piperidine] (6a) and their N-isopropyl derivatives (5b and 6b), DDSNPs, were synthesized. These compounds can be viewed as the result of the combination of the structure of the 3-(3,4-dihydroxyphenyl)-piperidine 2a or 2b, with the structure of the corresponding 1-(aminomethyl)-5,6-dihydroxy-(3a or 3b) or 1-(aminomethyl)-6,7-dihydroxy-1

  5,6-（5a）和6,7-二羟基-3,4-二氢螺[萘-1（2H）-3'-哌啶]（6a）及其N-异丙基衍生物（5b和6b），DDSNP，被合成。可以将这些化合物视为3-（3,4-二羟基苯基）-哌啶2a或2b的结构与相应的1-（氨基甲基）-5,6-二羟基-（ 3a或3b）或1-（氨基甲基）-6,7-二羟基-1,2,3,4-四氢萘（4a或4b），1-AMDTNs。通过结合实验和功能测试分析了新化合物（5a，b和6a，b）的α和β肾上腺素能，并将结果与​​儿茶酚胺1a，b和先前所述的3-（3）进行了比较。 ，4-二羟基苯基）哌啶（3-DPP； 2）和1-AMDTN（3、4）。
• Inhibitors of blood platelet aggregation. Activity of some 1H-benz[de]isoquinolinecarboximidamides on the in vivo blood platelet aggregation induced by collagen
  作者：Tom Beetz、Dick G. Meuleman、Joop H. Wieringa

  DOI：10.1021/jm00348a020

  日期：1982.6

  A series of 33 1H-benz[de]isoquinolinecarboximidamides has been prepared and tested in the rat after intraperitoneal (ip) and/or oral (po) administration for their ability to inhibit the in vivo blood platelet aggregation induced by collagen. In this aggregation test, a considerable number of active compounds were found. Fourteen compounds were active when administered in [0.2 (mmol/kg)/day], five of which also exhibited significant po activity. One compound was toxic after ip administration but was found to be active after po administration without apparent toxicity. It is thought that the solubility of the drug in water is an important factor for the resorption after oral administration and, hence, for its oral activity.
• Adrenergic compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0166937B1

  公开（公告）日：1991-08-28