2-(R,S)-丙基氨基-1,2,3,4-四氢萘 | 19485-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2-(R,S)-丙基氨基-1,2,3,4-四氢萘
• 英文名称: 2-(R,S)-Propylamino-1,2,3,4-tetrahydronaphthalene
• 英文别名: N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine；2-(N-propyl)amino-1,2,3,4-tetrahydronaphthalene；propyl-(1,2,3,4-tetrahydro-[2]naphthyl)-amine；Propyl-(1,2,3,4-tetrahydro-[2]naphthyl)-amin；propyl-(1,2,3,4-tetrahydro-naphthalen-2-yl)-amine
• CAS: 19485-87-1
• 化学式: C₁₃H₁₉N
• mdl: MFCD12146412
• 分子量: 189.301
• InChiKey: CHNZNFYUKYAHER-UHFFFAOYSA-N

物化性质

• 沸点：
  294.6±29.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(R,S)-丙基氨基-1,2,3,4-四氢萘 在 盐酸 、 palladium 10% on activated carbon 、 水 、 氢气 、 硝酸 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， -50.0~140.0 ℃ 、482.64 kPa 条件下， 反应 74.0h， 生成 N-(2-(4-phenylpiperazin-1-yl)ethyl)-N-propyl-5,6,7,8-tetrahydro-1H-naphtho[2,3-d]imidazol-6-amine
  参考文献：
  名称：

  Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: Impact on functional activity and selectivity for dopamine D2/D3 receptors

  摘要：

  The goal of the present study was to explore, in our previously developed hybrid template, the effect of introduction of additional heterocyclic rings (mimicking catechol hydroxyl groups as bioisosteric replacement) on selectivity and affinity for the D-3 versus D-2 receptor. In addition, we wanted to explore the effect of derivatization of functional groups of the agonist binding moiety in compounds developed by us earlier from the hybrid template. Binding affinity (K-i) of the new compounds was measured with tritiated spiperone as the radioligand and HEK-293 cells expressing either D-2 or D-3 receptors. Functional activity of selected compounds was assessed in the GTP gamma S binding assay. In the imidazole series, compound 10a exhibited the highest D-3 affinity whereas the indole derivative 13 exhibited similar high D-3 affinity. Functionalization of the amino group in agonist (+)-9d with different sulfonamides derivatives improved the D-3 affinity significantly with (+)-14f exhibiting the highest affinity. However, functionalization of the hydroxyl and amino groups of 15 and (+)-9d, known agonist and partial agonist, to sulfonate ester and amide in general modulated the affinity. In both cases loss of agonist potency resulted from such derivatization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.059
• 作为产物：
  描述：

  β-四氢萘酮 在 甲醇 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 生成 2-(R,S)-丙基氨基-1,2,3,4-四氢萘
  参考文献：
  名称：

  Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: Impact on functional activity and selectivity for dopamine D2/D3 receptors

  摘要：

  The goal of the present study was to explore, in our previously developed hybrid template, the effect of introduction of additional heterocyclic rings (mimicking catechol hydroxyl groups as bioisosteric replacement) on selectivity and affinity for the D-3 versus D-2 receptor. In addition, we wanted to explore the effect of derivatization of functional groups of the agonist binding moiety in compounds developed by us earlier from the hybrid template. Binding affinity (K-i) of the new compounds was measured with tritiated spiperone as the radioligand and HEK-293 cells expressing either D-2 or D-3 receptors. Functional activity of selected compounds was assessed in the GTP gamma S binding assay. In the imidazole series, compound 10a exhibited the highest D-3 affinity whereas the indole derivative 13 exhibited similar high D-3 affinity. Functionalization of the amino group in agonist (+)-9d with different sulfonamides derivatives improved the D-3 affinity significantly with (+)-14f exhibiting the highest affinity. However, functionalization of the hydroxyl and amino groups of 15 and (+)-9d, known agonist and partial agonist, to sulfonate ester and amide in general modulated the affinity. In both cases loss of agonist potency resulted from such derivatization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.059

文献信息

• 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。
• Comparison of biological effects of N-alkylated congeners of .beta.-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene
  作者：Joseph G. Cannon、Julio A. Perez、Jonathan P. Pease、John Paul Long、Jan R. Flynn、David B. Rusterholz、Stuart E. Dryer

  DOI：10.1021/jm00181a009

  日期：1980.7

  semirigid congeners of beta-phenethylamine have been prepared for evaluation of the effect of ring size (and of concomitant conformational variation) on biological activity in a variety of assays for adrenergic and dopaminergic actions. Pharmacologic activity was associated with 2-aminotetralin and 2-aminoindan derivateves, but was not found with 6-aminobenzocycloheptene derivatives. Noteworthy is the

  已经准备了三个系列的β-苯乙胺双环，半刚性同源物，用于评估在各种肾上腺素能和多巴胺能作用的测定中环大小（以及伴随的构象变化）对生物活性的影响。药理活性与2-氨基四氢萘和2-氨基茚满衍生物有关，但与6-氨基苯并环庚烯衍生物未发现。值得注意的是几种氨基四氢化萘和氨基茚满在不引起多巴胺能作用的情况下增加热板反应时间的能力。纳洛酮预处理不阻止该作用。
• 2-Propylamino-tetralin derivatives for reducing intraocular pressure
  申请人：Whitby Research Incorporated

  公开号：EP0230629A2

  公开（公告）日：1987-08-05

  This invention provides a method for reducing the intraocular pressure in mammals which comprises administering an effective amount of a compound selected from the group consisting of compounds represented by the general formula: where R2, R3 and R4 are each selected from the group consisting of H, and OA; A is H or -Rs; R5 is selected from the group consisting of alkyl and aromatic residues; n is 2 or 3; and R, is selected from the group consisting of 3-hydroxyphenyl, 4-hydroxyphenyl, 3-pyridyl, 4-pyridyl, where X is S, O or NH, with the proviso that at least one of R2, R3 and R4 is H, that at least one of R2, R3 and R4 is not H and that R2 and R4 are not both OA; and pharmaceutically-acceptable salts thereof. This invention further provides compositions useful in such method of reducing the intraocular pressure in mammals.

  本发明提供了一种降低哺乳动物眼内压的方法，该方法包括施用有效量的选自通式所代表化合物组成的组的化合物： 其中R2、R3和R4各自选自由H和OA组成的组；A为H或-Rs；R5选自由烷基和芳香残基组成的组；n为2或3；R选自由3-羟基苯基、4-羟基苯基、3-吡啶基、4-吡啶基组成的组、 其中 X 是 S、O 或 NH，但 R2、R3 和 R4 中至少有一个是 H，R2、R3 和 R4 中至少有一个不是 H，且 R2 和 R4 不是都是 OA；及其药学上可接受的盐。本发明进一步提供了在这种降低哺乳动物眼内压的方法中有用的组合物。
• Dérivés de 4-(aminométhyl)pipéridine, leur préparation et leur application en thérapeutique
  申请人：SYNTHELABO

  公开号：EP0447292A1

  公开（公告）日：1991-09-18

  Composés de formule générale (I) dans laquelle n représente le nombre 1 ou 2, et R représente un groupe alkyle linéaire ou ramifié en C1-C3 et X représente un ou plusieurs substituants choisis parmi les atomes d'hydrogène et d'halogène et les groupes alkyles en C1-C3 et alcoxy en C1-C3. Application en thérapeutique.

  通式(I)化合物 其中 n 代表数字 1 或 2，以及 R 代表直链或支链 C1-C3 烷基，以及 X 代表一个或多个取代基，选自氢、卤素原子、C1-C3 烷基和 C1-C3 烷氧基。 治疗应用。
• Cymerman Craig et al., Australian Journal of Chemistry, 1959, vol. 12, p. 447,450,451
  作者：Cymerman Craig et al.

  DOI：——

  日期：——