di-n-propyl-5,6,7,8-tetrahydro-1,7-naphtahalenediamine dichloride | 81185-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: di-n-propyl-5,6,7,8-tetrahydro-1,7-naphtahalenediamine dichloride
• 英文别名: 8-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene；N7,N7-Dipropyl-5,6,7,8-tetrahydro-1,7-naphthalenediamine；8-amino-2-dipropylamino-1,2,3,4-tetrahydronaphthalene；8-Amino-2-(di-n-propylamino)tetralin；7-N,7-N-dipropyl-5,6,7,8-tetrahydronaphthalene-1,7-diamine
• CAS: 81185-25-3
• 化学式: C₁₆H₂₆N₂
• 分子量: 246.396
• InChiKey: GKXCRUNVLJPRBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  di-n-propyl-5,6,7,8-tetrahydro-1,7-naphtahalenediamine dichloride 在 sodium nitrite 作用下， 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 硫酸 、 水 为溶剂， 以48%的产率得到(+/-)-8-cyano-2-(dipropylamino)tetralin
  参考文献：
  名称：

  8-Substituted 2-aminotetralins

  摘要：

  新的8-取代的2-氨基四氢萘可以从相应的氨基四氢萘或四氢萘酮制备而成。它们可以用于药物。

  公开号：

  US04873262A1
• 作为产物：
  描述：

  2-溴苯乙酰氯 在 盐酸 、 正丁基锂 、 三氯化铝 、 sodium azide 、 硫酸 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 80.0h， 生成 di-n-propyl-5,6,7,8-tetrahydro-1,7-naphtahalenediamine dichloride
  参考文献：
  名称：

  5-, 6-, 7- and 8-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalenes: centrally acting DA and 5-HT1A agonists

  摘要：

  5-, 6-, 7- and 8-Amino-2-(NN-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene were synthesized and compared with the corresponding phenolic compounds in vivo and in vitro for their effects on central serotonergic (5-HT1A) and dopaminergic (D2) systems. The 5- and 8-amino isomers surprisingly showed a 100-fold lower affinity for D2 and 5-HT1A receptors, respectively, than their corresponding phenols. This was also reflected in vivo. The 6-amino- and hydroxy-isomers were equipotent, while the 7-amino compound showed in vivo effects both on dopaminergic and serotonergic systems, the latter not being noticed in vitro. Intermediates 8-bromo-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene and 2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene-8-carboxylic acid methyl ester were also tested and found to be quite potent 5-HT1A agonists.

  DOI：

  10.1016/0223-5234(93)90028-d

文献信息

• 6,7,8,9-Tetrahydro-1H-benz(g)indol-8-amine derivatives
  申请人：Ayerst, McKenna & Harrison, Inc.

  公开号：US04510157A1

  公开（公告）日：1985-04-09

  Herein is disclosed compounds of the formula ##STR1## in which R.sup.1,R.sup.2,R.sup.3,R.sup.4 and R.sup.5 each is hydrogen or lower alkyl, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the compounds and pharmaceutical compositions. The compounds exhibit dopamine-receptor stimulating activity in a mammal and are useful for treating hyperprolactinemia, galactorrhea, amenorrhea, impotence, Parkinsonism, diabetes, acromegaly, hypertension and other central nervous system disorders.

  本公开了以下式的化合物##STR1##其中R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5分别是氢或较低的烷基，其治疗上可接受的酸盐，其制备方法，使用这些化合物的方法以及药物组合物。这些化合物在哺乳动物中表现出多巴胺受体刺激活性，并可用于治疗高催乳素血症、乳汁分泌、闭经、阳痿、帕金森病、糖尿病、肢端肥大症、高血压和其他中枢神经系统疾病。
• Halo substituted aminotetralins
  申请人：The Upjohn Company

  公开号：US05225596A1

  公开（公告）日：1993-07-06

  This invention is therapeutically useful tetralins and pharmaceutically acceptable acid addition salts thereof of the formula ##STR1## wherein X.sub.1 is halogen, CF.sub.3, --OR.sub.3, or --SR.sub.4 ; wherein R.sub.3 is alkyl(C.sub.1 -C.sub.8); alkenyl(C.sub.1 -C.sub.8); --CH.sub.2 -cycloalkyl(C.sub.3 -C.sub.8) or benzyl; wherein R.sub.4 is alkyl(C.sub.1 -C.sub.3); wherein X.sub.2 is hydrogen, CF.sub.3 or halogen; wherein R.sub.7 is hydrogen or methyl; wherein R.sub.1 is hydrogen, alkyl(C.sub.1 -C.sub.3), or cyclopropylmethyl; wherein R.sub.2 is --CH.sub.2 -cycloalkyl(C.sub.3 -C.sub.8), alkyl(C.sub.1 -C.sub.8), --(CH.sub.2).sub.q --R.sub.5 or --CH.sub.2 CH.sub.2 --Z--(CH.sub.2).sub.r CH.sub.3 ; wherein R.sub.5 is phenyl, 2-thiophene or 3-thiophene; wherein Z is oxygen or sulfur; and wherein p is one or 2, q is 2 or 3, and r is zero to 3; with the provisos that (1) when X.sub.1 is --OR.sub.3, X.sub.2 is halogen or CF.sub.3 ; and (2) when X.sub.1 is halogen, X.sub.2 is hydrogen, and p is 2, X.sub.1 is in a position other than the 8-position. These compounds are useful to treat central nervous system disorders.

  本发明涉及具有治疗作用的四氢萘类化合物及其药学上可接受的酸盐，其化学式为：##STR1##其中X.sub.1为卤素、CF.sub.3、--OR.sub.3或--SR.sub.4；其中R.sub.3为烷基（C.sub.1-C.sub.8）、烯基（C.sub.1-C.sub.8）、--CH.sub.2-环烷基（C.sub.3-C.sub.8）或苄基；其中R.sub.4为烷基（C.sub.1-C.sub.3）；其中X.sub.2为氢、CF.sub.3或卤素；其中R.sub.7为氢或甲基；其中R.sub.1为氢、烷基（C.sub.1-C.sub.3）或环丙基甲基；其中R.sub.2为--CH.sub.2-环烷基（C.sub.3-C.sub.8）、烷基（C.sub.1-C.sub.8）、--（CH.sub.2）.sub.q--R.sub.5或--CH.sub.2 CH.sub.2--Z--（CH.sub.2）.sub.r CH.sub.3；其中R.sub.5为苯基、2-噻吩或3-噻吩；其中Z为氧或硫；其中p为1或2，q为2或3，r为0至3；但有以下条件：（1）当X.sub.1为--OR.sub.3时，X.sub.2为卤素或CF.sub.3；（2）当X.sub.1为卤素，X.sub.2为氢，且p为2时，X.sub.1在8位以外的位置。这些化合物可用于治疗中枢神经系统疾病。
• 7,8,9,10-Tetrahydrobenzo[h]quinolin-9-amine derivatives and compositions
  申请人：Ayerst, McKenna & Harrison, Ltd.

  公开号：US04521423A1

  公开（公告）日：1985-06-04

  7,8,9,10-Tetrahydrobenzo[h]quinolin-9-amine derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is hydrogen or lower alkyl, or R.sup.1 and R.sup.2 together form a chain of the formula --(CH.sub.2).sub.n -- where n is the integer 4, 5 or 6, are useful for treating depression.

  公式为##STR1##的7,8,9,10-四氢苯并[h]喹啉-9-胺衍生物，其中R.sup.1和R.sup.2分别独立地为氢或低碳基，或者R.sup.1和R.sup.2共同形成公式--(CH.sub.2).sub.n--的链，其中n为整数4、5或6，用于治疗抑郁症。
• 8-Substituierte 2-Aminotetraline
  申请人：BAYER AG

  公开号：EP0272534A2

  公开（公告）日：1988-06-29

  Neue 8-substituierte 2-Aminotetraline können aus den entsprechenden Aminotetralinen oder Tetralonen hergestellt werden. Sie können in Arzneimitteln verwendet werden.

  从相应的氨基四氢萘或四氢萘酮中可以制备出新的 8-取代 2-氨基四氢萘，并可用于制药。
• 6,7,8,9-Tetrahydro-N,N-di-n-propyl-3H-benzindol-8-amines. Derivatives as Potent and Orally Active Serotonin 5-HT1A Receptor Agonists
  作者：Peter Stjernloef、Thomas Elebring、Jonas Nilsson、Bengt Andersson、Soeren Lagerkvist、Kjell Svensson、Agneta Ekman、Arvid Carlsson、Haakan Wikstroem

  DOI：10.1021/jm00046a010

  日期：1994.9

  Derivatives and isosteric derivatives of the potent 5-HT1A agonist 8-(di-n-propylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole- 1-carbaldehyde (5) were prepared and evaluated in vivo and in vitro for serotonergic and dopaminergic activity. The 1-cyano analog 8 was found to be almost equipotent to 5 and the previously described 2-cyano derivative 6, while a I-chloro and 1-(1,1,1-trifluoroethyl) substituent (9 and 10, respectively) formed less potent derivatives. The isosteric 6,7,8,9-tetrahydro-1H-benz[g]indoles 4 and 12-15 showed surprisingly low affinity or activity at both serotonergic and dopaminergic systems. The interpretations of these results by means of drug-receptor interactions at the 5-HT1A subtype are discussed. Compounds 6 and 8 were found to have high oral bioavailability in the rat (63% and 54%, respectively).