(7-甲氧基-1,2,3,4-四氢-萘-2-基)-丙基-胺 | 148258-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: (7-甲氧基-1,2,3,4-四氢-萘-2-基)-丙基-胺
• 英文名称: (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine
• 英文别名: (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine；(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine；(+/-)-7-methoxy-2-(N-n-propylamino)tetralin；7-methoxy-2-(N-propylamino)tetralin；7-Methoxy-2-(R,S)-propylamino-1,2,3,4-tetrahydronaphthalene；7-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 148258-42-8
• 化学式: C₁₄H₂₁NO
• 分子量: 219.327
• InChiKey: RMRODALMKPMZFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (7-甲氧基-1,2,3,4-四氢-萘-2-基)-丙基-胺 在 吡啶 、 盐酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 2,2,2-trifluoro-N-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide
  参考文献：
  名称：

  4-PIPERIDINYL ALKYL AMINE DERIVATIVES AS MUSCARINIC RECEPTOR ANTAGONISTS

  摘要：

  本发明涉及一般为毒蕈碱受体拮抗剂的化合物，这些化合物由通式I表示： 1 其中p、R1、R2、R3和A如说明书中所定义，或为单个异构体、消旋或非消旋异构体混合物，或为其可接受的盐或溶剂合物。本发明还涉及含有此类化合物的药物组合物，以及将其作为治疗药物使用和制备的方法。

  公开号：

  US20030162780A1
• 作为产物：
  描述：

  (7-甲氧基-1,2,3,4-四氢萘-2-基)丙胺盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (7-甲氧基-1,2,3,4-四氢-萘-2-基)-丙基-胺
  参考文献：
  名称：

  Discovery of 4-(4-(2-((5-Hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)ethyl)piperazin-1-yl)quinolin-8-ol and Its Analogues as Highly Potent Dopamine D2/D3 Agonists and as Iron Chelator: In Vivo Activity Indicates Potential Application in Symptomatic and Neuroprotective Therapy for Parkinson’s Disease

  摘要：

  The role of iron in the pathogenesis of Parkinson's disease (PD) has been implicated strongly because of generation of oxidative stress leading to dopamine cell death. In our overall goal to develop bifunctional/multifunctional drugs, we designed dopamine D2/D3 agonist molecules with a capacity to bind to iron. Binding assays were carried out with HEK-293 cells expressing either D2 or D3 receptor with tritiated spiperone to evaluate inhibition constants (K-i). Functional activity of selected compounds was carried out with GTP gamma S binding assay. SAR results identified compounds (+)-19a and (-)-19b as two Potent agonists for both D2 and D3 receptors (EC50 (GTP gamma S); D2 = 4.51 and 1.69 nM and D3 = 1.58 and 0.74 nM for (-)-19b and (+)-19a, respectively). In vitro complexation Studies with 19b demonstrated efficient chelation with iron. Furthermore, the deoxyribose assay with 19b demonstrated potent antioxidant activity. In PD animal model study, (-)-19b exhibited potent in vivo activity in reversing locomotor activity in reserpinized rats and also in producing potent rotational activity in 6-OHDA lesioned rats. This reports initial development of unique lead molecules that might find potential use in Symptomatic and neuroprotective treatment of PD.

  DOI：

  10.1021/jm901618d

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.

  这项发明是治疗上有用的四氢萘和其药用可接受的酸盐，其化学式为##STR1##其中YR.sub.1是在8位处为OR.sub.1，其中R.sub.1为--CH.sub.2--(C.sub.3-8环烷基)；R.sub.2为氢或C.sub.1-3烷基；R.sub.3为--CH.sub.2--(C.sub.3-8环烷基)；R.sub.4为氢，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.n CH.sub.3；n为0至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，其带有一个或两个来自氯、溴或氟的取代基；并且，如果R.sub.3含有超过四个碳原子且R.sub.4为烷基，则所述烷基含有1至3个碳原子。或者，--YR.sub.1为芳环上的5、6、7或8位处为--S--(C.sub.1-3烷基)，或在8位处为OR.sub.1，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为氢或(C.sub.1-C.sub.3)烷基；R.sub.3为--CH.sub.2--(C.sub.3-C.sub.8)环烷基；R.sub.4为--(CH.sub.2).sub.m--(2-噻吩基或3-噻吩基)；m为2或3。
• Dopamine D-3 and serotonin (5-HT.sub.1A) receptor ligands and imaging
  申请人：The Trustees of the University of Pennsylvania

  公开号：US05690906A1

  公开（公告）日：1997-11-25

  Tetralin derivatives, such as 7-hydroxy-2-(N-n-propyl-N-3 '-iodo-2'-propenyl)-amino!tetralin and 8-hydroxy-2-(N-n-propyl-N-3 '-iodo-2'-propenyl)amino-tetralin, are disclosed which have affinity and specificity for dopamine D-3 and/or serotonin 5-HT.sub.1A receptors.

  四氢萘衍生物，如7-羟基-2-(N-丙基-N-3'-碘-2'-丙烯基)-氨基四氢萘和8-羟基-2-(N-丙基-N-3'-碘-2'-丙烯基)氨基四氢萘，具有对多巴胺D-3和/或5-HT.sub.1A受体的亲和力和特异性。
• Substituted 2-aminotetralins
  申请人：Whitby Research, Inc.

  公开号：US05274003A1

  公开（公告）日：1993-12-28

  Optically active or racemic compounds are provided having the formula ##STR1## where R.sub.2, R.sub.3 and R.sub.4 are each selected from the group consisting of H and OH with the provision that at least one of R.sub.2, R.sub.3 and R.sub.4 is H, that R.sub.2 and R.sub.4 are not both OH; X is oxygen; and R.sub.1 is selected from the group consisting of ##STR2## wherein Z is oxygen, nitrogen or sulfur, wherein Y is selected from the group consisting of hydroxy, nitro, cyano, azido, amino, acylamino, carboxyamido, trifluoromethyl, sulfate, sulfonamido, halogen, hydrocarbyl and heteroatom-substituted hydrocarbyl radicals, wherein said heteroatoms are selected from the group consisting of halogen, nitrogen, oxygen, sulfur and phosphorus and said hydrocarbyl radicals comprise from 1 to 12 carbon atoms, and a is an integer of from zero to 3. These compounds are capable of binding selectivity of one or more dopamine D.sub.2 receptors, for instance, in humans. They are useful in treatment of disorders of the central nervous, cardiovascular, and endocrine systems, such as elevated intraocular pressure, schizophrenia and Parkinsonism, and for inducing anorexia and weight loss in humans and other mammals.

  提供具有以下公式的光学活性或拉克米化合物##STR1##其中R.sub.2、R.sub.3和R.sub.4分别从H和OH组成的组中选择，但至少其中一个为H，且R.sub.2和R.sub.4不能同时为OH；X为氧；R.sub.1从以下组成的组中选择##STR2##其中Z为氧、氮或硫，Y从羟基、硝基、氰基、叠氮基、氨基、酰胺基、羧胺基、三氟甲基、硫酸盐、磺酰胺基、卤素、烃基和杂原子取代的烃基基团组成的组中选择，其中这些杂原子从卤素、氮、氧、硫和磷组成的组中选择，而这些烃基基团由1至12个碳原子组成，a为0至3的整数。这些化合物能够选择性结合一个或多个多巴胺D.sub.2受体，例如在人类中。它们在治疗中枢神经、心血管和内分泌系统的疾病方面有用，如提高眼内压、精神分裂症和帕金森病，以及诱导人类和其他哺乳动物产生厌食和体重减轻。
• Benzocycloalkylenylamine derivatives as muscarinic receptor antagonists
  申请人：——

  公开号：US20020004494A1

  公开（公告）日：2002-01-10

  This invention relates to compounds which are generally muscarinic M2/M3 receptor antagonists and which are represented by Formula I: 1 wherein X, Y, and Z are O, S, or NR 4 , and the other substituents are as defined in the specification; and prodrugs, individual isomers, racemic or non-racemic mixtures of isomers, and pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds and methods for their use as therapeutic agents.

  本发明涉及一般为肌胆碱M2/M3受体拮抗剂的化合物，其由式I表示：其中X、Y和Z为O、S或NR4，其他取代基如规范中定义；以及这些化合物的前药、单体异构体、外消旋或非外消旋异构体混合物，以及其药用可接受的盐或溶剂合物。该发明还涉及含有这些化合物的药物组合物以及它们作为治疗剂的使用方法。
• Affinity for Dopamine D₂, D₃, and D₄ Receptors of 2-Aminotetralins. Relevance of D₂ Agonist Binding for Determination of Receptor Subtype Selectivity
  作者：L. Alexander van Vliet、Pieter G. Tepper、Durk Dijkstra、Geert Damsma、Håkan Wikström、Thomas A. Pugsley、Hyacinth C. Akunne、Thomas G. Heffner、Shelly A. Glase、Lawrence D. Wise

  DOI：10.1021/jm960345l

  日期：1996.1.1

  D3 DA receptors, as exemplified by compounds 11-15 and 21-26, while some had a reasonable selectivity for the DA D3 receptors. The affinities of the 2-aminotetralins for the D21, receptor depended on the type of radioligand (agonist or antagonist) used. The agonist affinity data, obtained by using the agonist ligand [3H]N-0437, are thought to be more relevant for calculating DA receptor subtype selectivity

  制备了一系列2-氨基四氢化萘，在5-或7位上被甲氧基或羟基取代，并具有不同的N-烷基或N-芳基烷基取代基，并在人多巴胺（DA）D2的结合测定中进行了评估，D3和D4受体。该系列的某些成员是在以前的研究中准备的，但从未在体外用单受体亚型进行测试，因此再次进行了检查。所测试的2-氨基四氢化萘均未显示出对多巴胺D4受体的高亲和力。但是，如化合物11-15和21-26所示，许多2-氨基四氢萘林对D2和D3 DA受体均显示出高亲和力，而有些对DA D3受体具有合理的选择性。2-氨基四氢萘林对D21受体的亲和力取决于所用放射性配体（激动剂或拮抗剂）的类型。激动剂亲和力数据，