(+/-)-2-(dipropylamino)tetralin-8-carboxylic acid | 117347-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-2-(dipropylamino)tetralin-8-carboxylic acid
• 英文别名: 8-carboxy-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalene；2-dipropylamino-1,2,3,4-tetrahydronaphthalene-8-carboxylic acid；8-Carboxy-2-(dipropylamino)tetralin；2-(Di-n-propylamino)-8-carboxy-1,2,3,4-tetrahydronaphthalene；7-(dipropylamino)-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid
• CAS: 117347-18-9
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: ZMAPYOVSTJPKMC-UHFFFAOYSA-N

物化性质

• 沸点：
  423.2±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(dipropylamino)tetralin-8-carboxylic acid 在 草酸氯化物 、 二环己胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 (+/-)-methyl 2-(dipropylamino)tetralin-8-carboxylate
  参考文献：
  名称：

  Novel [(diazomethyl)carbonyl]-1,2,3,4-tetrahydronaphthalene derivatives as potential photoaffinity ligands for the 5-HT1A receptor

  摘要：

  The photolabile (diazomethyl)carbonyl function was introduced into the 8-position of 2-(N,N-di-n-propyl-amino)-1,2,3,4-tetrahydronaphthalene in three ways, resulting in the ether 8-[[(diazomethyl)carbonyl]methoxy]-2-(N,N-di-n-propylamino)-1,2,3,4- tetrahydronaphthalene (2), the ester 8-(diazoacetoxy)-2-(N,N-di-n-propyl-amino)-1,2,3,4- tetrahydronaphthalene (3), and the ketone 8-[(diazomethyl)carbonyl]-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (4). Specific binding of these compounds at the 5-hydroxytryptamine1A sites in rat brain membranes labeled with 1 nM [3H]-8-hydroxy-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (8-OH-DPAT) showed IC50 values of ca. 75, 125, and 25 nM, respectively, for the three compounds. Photolysis of methanolic solutions of 2-4 in the absence of receptor proteins lead in each case to an abundance of Wolff-rearranged products. In the case of ether 2, subsequent beta-elimination to 8-OH-DPAT removed this compound from serious consideration as a photoaffinity ligand. Ester 3 and ketone 4 were photolysed in vitro. Whereas ester 3 was ineffective in decreasing the specific binding of [3H]-8-OH-DPAT, ketone 4 decreased 40% of the specific binding of [3H]-8-OH-DPAT in the presence (but not the absence) of ultraviolet light. Thus this ketone emerges from these studies as a good candidate for a photoaffinity label for the 5-hydroxytrypatamine1A receptor.

  DOI：

  10.1021/jm00165a011
• 作为产物：
  描述：

  2-溴苯乙酰氯 在 platinum(IV) oxide 正丁基锂 、 三氯化铝 、 氢气 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 98.0h， 生成 (+/-)-2-(dipropylamino)tetralin-8-carboxylic acid
  参考文献：
  名称：

  Novel [(diazomethyl)carbonyl]-1,2,3,4-tetrahydronaphthalene derivatives as potential photoaffinity ligands for the 5-HT1A receptor

  摘要：

  The photolabile (diazomethyl)carbonyl function was introduced into the 8-position of 2-(N,N-di-n-propyl-amino)-1,2,3,4-tetrahydronaphthalene in three ways, resulting in the ether 8-[[(diazomethyl)carbonyl]methoxy]-2-(N,N-di-n-propylamino)-1,2,3,4- tetrahydronaphthalene (2), the ester 8-(diazoacetoxy)-2-(N,N-di-n-propyl-amino)-1,2,3,4- tetrahydronaphthalene (3), and the ketone 8-[(diazomethyl)carbonyl]-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (4). Specific binding of these compounds at the 5-hydroxytryptamine1A sites in rat brain membranes labeled with 1 nM [3H]-8-hydroxy-2-(N,N-di-n-propylamino)- 1,2,3,4-tetrahydronaphthalene (8-OH-DPAT) showed IC50 values of ca. 75, 125, and 25 nM, respectively, for the three compounds. Photolysis of methanolic solutions of 2-4 in the absence of receptor proteins lead in each case to an abundance of Wolff-rearranged products. In the case of ether 2, subsequent beta-elimination to 8-OH-DPAT removed this compound from serious consideration as a photoaffinity ligand. Ester 3 and ketone 4 were photolysed in vitro. Whereas ester 3 was ineffective in decreasing the specific binding of [3H]-8-OH-DPAT, ketone 4 decreased 40% of the specific binding of [3H]-8-OH-DPAT in the presence (but not the absence) of ultraviolet light. Thus this ketone emerges from these studies as a good candidate for a photoaffinity label for the 5-hydroxytrypatamine1A receptor.

  DOI：

  10.1021/jm00165a011

文献信息

• 8-Substituted 2-aminotetralins
  申请人：Bayer Aktiengesellschaft

  公开号：US04873262A1

  公开（公告）日：1989-10-10

  New 8-substituted 2-aminotetralins can be prepared from the corresponding aminotetralins or tetralones. They can be used in medicaments.

  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。
• 8-substituted-2-aminotetralins
  申请人：Astra Aktiebolag

  公开号：US05635537A1

  公开（公告）日：1997-06-03

  A compound of the formula ##STR1## Z is hydrogen or halogen, Q is COR.sup.1 or 5-or 6-membered aryl which may contain 1 or 2 heteroatoms selected from N, 0 or S and may be substituted or fused wherein R is hydrogen or C.sub.1 -methyl (cis-configuration), R.sup.1 is C.sub.1 -C.sub.6 alkyl or an aromatic ring which may contain heteroatoms selected from O and S and may be substituted or fused to an optionally substituted benzene ring, R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sup.3 may be different groups defined in claim 1, and enantiomers/salts thereof, processes for preparation of said compounds, pharmaceutical preparations containing said compounds, use of and method of treatment of disorders in CNS by using said compounds.

  公式##STR1##的化合物，其中Z是氢或卤素，Q是COR.sup.1或5-或6-成环的芳基，其中芳基可能含有1或2个杂原子，杂原子选自N、O或S，并且芳基可能是取代的或与一个可选地取代的苯环融合；R是氢或C.sub.1 -甲基（顺式构型），R.sup.1是C.sub.1 -C.sub.6烷基或含有杂原子的芳香环，杂原子选自O和S，并且芳香环可能是取代的或与一个可选地取代的苯环融合；R.sup.2是氢或C.sub.1 -C.sub.6烷基；R.sup.3可以是权利要求1中定义的不同基团，以及它们的对映体/盐，制备所述化合物的方法，含有所述化合物的药物制剂，以及使用所述化合物治疗中枢神经系统疾病的方法。
• Derivatives of 2-(dipropylamino)tetralin: effect of the C8-substituent on the interaction with 5-HT1A receptors
  作者：Ye Liu、Hong Yu、Bjoern E. Svensson、Lourdes Cortizo、Tommy Lewander、Uli Hacksell

  DOI：10.1021/jm00078a012

  日期：1993.12

  devoid of 5-HT1A receptor affinity, the compounds have moderate to high affinities (K(i) values range from 0.7 to 130 nM) for 5-HT1A receptors. Surprisingly, several of the derivatives do not produce any apparent effects in vivo although they have fairly high 5-HT1A receptor affinities. However, the methoxycarbonyl- and acetyl-substituted derivatives are potent 5-HT1A receptor agonists in vivo and exhibit

  制备了一系列其中C8取代基不同的2-（二丙基氨基）四氢萘衍生物，并进行了药理学评价，以探讨C8取代基在基于2-氨基四氢萘的配体与血清素（5-HT1A）受体相互作用中的重要性。通过8-羟基-2-（二丙基氨基）四氢化萘（8-OH-DPAT，1）的对映异构体的三平面的钯催化反应制备对映纯衍生物。通过与[3H] -8-OH-DPAT在大鼠海马和皮层组织中的竞争实验，评估了化合物对5-HT1A受体的亲和力。另外，通过在大鼠中使用生化和行为测定，评估了化合物在体内对中心5-HT和多巴胺受体的刺激活性。除了没有5-HT1A受体亲和力的羧基取代的衍生物外，这些化合物对5-HT1A受体具有中等至高的亲和力（K（i）值在0.7到130 nM之间）。出乎意料的是，尽管几种衍生物具有相当高的5-HT1A受体亲和力，但它们在体内没有产生任何明显的作用。但是，甲氧基羰基和乙酰基取代的衍生物在体内是有效的5-HT1A受
• 5-, 6-, 7- and 8-amino-2-(N,N-di-n-propylamino)-1,2,3,4-tetrahydronaphthalenes: centrally acting DA and 5-HT1A agonists
  作者：P Stjernlöf、T Elebring、B Andersson、A Svensson、K Svensson、A Ekman、A Carlsson、H Wikström

  DOI：10.1016/0223-5234(93)90028-d

  日期：1993.1

  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.
• KLINE, TONI B.;NELSON, DAVID L.;NAMBOODIRI, KRISHNAN, J. MED. CHEM., 33,(1990) N, C. 950-955
  作者：KLINE, TONI B.、NELSON, DAVID L.、NAMBOODIRI, KRISHNAN

  DOI：——

  日期：——