4-(3-bromo-n-propyl)-1,2-dihydronaphthalene | 21568-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(3-bromo-n-propyl)-1,2-dihydronaphthalene
• 英文别名: 4-(3-Bromopropyl)-1,2-dihydronaphthalene
• CAS: 21568-71-8
• 化学式: C₁₃H₁₅Br
• 分子量: 251.166
• InChiKey: LIOYTGSHSSATBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-(3-bromo-n-propyl)-1,2-dihydronaphthalene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以90%的产率得到1-(3-溴-n-丙基)-1,2,3,4-四氢萘
  参考文献：
  名称：

  对1-芳基-4- [1-四氢]烷基]哌嗪的5-HT1A受体具有高亲和力和选择性。2。

  摘要：

  为了增加5-HT1A对D-2，α1，σ和其他5-HT受体的选择性，合成了几种在侧链末端具有四氢萘部分的4-烷基-1-芳基哌嗪。许多变化已影响先前的类型3（1-芳基-4- [3-（1,2-二氢萘-4-基）-正丙基]哌嗪的结构。遵循几种合成程序以获得最终产物，这取决于双键以及侧链上杂原子的存在与否。在第一种情况下，可以广泛使用格利雅（Grignard）反应，而在第二种情况下，可以采用常规的合成方法。通过放射受体结合试验评估最终化合物对多巴胺D-1和D-2、5-羟色胺5-HT1A，5-HT1B，5-HT1C和5-HT2，α1肾上腺素和sigma受体的体外活性。

  DOI：

  10.1021/jm00006a013
• 作为产物：
  描述：

  1-cyclopropyl-1-tetralol 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 4-(3-bromo-n-propyl)-1,2-dihydronaphthalene
  参考文献：
  名称：

  1-四氢萘酮和相关化合物的一些烷基化和格氏反应

  摘要：

  描述了产生2-单烷基-和2，2-二烷基-1-四氢萘酮的简便途径。各种1-（氨基烷基）-3，4-二氢萘和1-（氨基亚烷基）-1，2，3，4-四氢萘是通过在适当的1-四氢萘酮上进行格氏反应的方法制备的。报道了使用4-苯并二氢吡喃酮和相关化合物的类似实验。

  DOI：

  10.1039/j39690000217

文献信息

• Mixed 5-HT1A/D-2 activity of a new model of arylpiperazines: 1-aryl-4-[3-(1,2-dihydronaphthalen-4-yl)-n-propyl]piperazines. 1. Synthesis and structure-activity relationships
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Vincenzo Tortorella、Francesco Fiorentini、Vincenzo Olgiati、Ermes Vanotti、Stefano Govoni

  DOI：10.1021/jm00027a012

  日期：1994.1

  and dopaminergic activity and to pursue the recent alternative approaches to the discovery of novel antipsychotic and anxiolytic agents. Title compounds were evaluated for in vitro activity on dopamine D-2 and serotonin 5-HT1A and 5-HT2 receptors by radioreceptor binding assays. They show high nanomolar affinity for 5-HT1A, moderate affinity for D-2, and low affinity for 5-HT2 receptors, and in particular

  合成了在烷基链上包含末端二氢萘片段的4-烷基-1-芳基哌嗪的新模型，以具有混合的血清素能和多巴胺能活性，并寻求发现新型抗精神病药和抗焦虑药的最新方法。通过放射受体结合测定法评价标题化合物对多巴胺D-2和5-羟色胺5-HT1A和5-HT2受体的体外活性。它们显示出对5-HT1A的高纳摩尔亲和力，对D-2的中等亲和力，对5-HT2受体的低亲和力，尤其是两种化合物4- [3-（1,2-二氢-6-甲氧基萘-4 -基）-正丙基] -1-（2-甲氧基苯基）哌嗪（8）和4- [3-（1,2-二氢-8-甲氧基萘-4-基）-正丙基] -1-（ 2-吡啶基）哌嗪（15），显示5-HT1A的IC50 = 2.0和1.4的值（nM），D-2的IC50 = 90.6和119.3的值（nM），分别。一些体内行为研究表明化合物8是5-HT1A受体的拮抗剂。这些最初的发现使新的芳基哌嗪与阿扎斯匹隆类化合物处于同一水平，例如1-（2-甲氧基苯基）-4-
• New σ and 5-HT_1A Receptor Ligands:  ω-(Tetralin-1-yl)-<i>n</i>-alkylamine Derivatives
  作者：Francesco Berardi、Nicola A. Colabufo、Giuseppe Giudice、Roberto Perrone、Vincenzo Tortorella、Stefano Govoni、Laura Lucchi

  DOI：10.1021/jm950409c

  日期：1996.1.1

  Two series of compounds that are structurally related to benzomorphans, derived by structural modification of arylpiperazines with high 5-HT1A affinity and moderate a affinity, were prepared in order to increase a affinity and selectivity. All new compounds are N-substituted-omega-(1,2,3,4-tetrahydronaphthalen-1-yl)- or -omega-(1,2-dihydronaphthalen-4-yl)-n-alkylamines with, in some cases, a methoxy group on the tetralin moiety. They were tested in radioligand binding assays on sigma ([H-3]DTG and [H-3]-(+)-pentazocine), D-2 dopaminergic, 5-HT1A and 5-HT2 serotonergic, and PCP (phencyclidine) receptors. A first set of compounds bearing a 4-(1-substituted)piperazine moiety as terminal fragment on the alkyl chain showed moderate to high sigma affinity (K-i = 5.3-139 nM), the most active and selective being 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-proyl]piperazine (14), with probable pronounced alpha(2) affinity (K-i = 5.3 nM on [H-3]DTG and K-i = 71 nM on [H-3]-(+)-pentazocine). Moreover, compound 13, a 1-benzylpiperazine analogue of 14, preserved a dual high 5-HT1A and sigma affinity (K-i = 3.6 nM on [H-3]-5-HT and K-i = 7.0 nM on [H-3]DTG). The second set of compounds includes some N-phenylalkyl derivatives of 3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propylamine that can be considered. to be open-chain derivatives of 4-substituted-1-arylpiperazines. Among these compounds that had a lower activity toward sigma binding sites, a high 5-HT1A affinity was found for the N-(3-phenylpropyl) derivative 21 (K-i = 4.4 nM) which demonstrated very good selectivity.
• Perrone, Roberto; Berardi, Francesco; Colabufo, Nicola A., Medicinal Chemistry Research, 1997, vol. 7, # 2, p. 76 - 86
  作者：Perrone, Roberto、Berardi, Francesco、Colabufo, Nicola A.、Leopoldo, Marcello、Lograno, Marcello D.、Tortorella, Vincenzo

  DOI：——

  日期：——
• [EN] VERAPAMIL ANALOGUES WITH INHIBITION ACTIVITY ON ABC (ATP BINDING CASSETTE) CELL EXTRUSION PUMPS<br/>[FR] Analogues du vérapamil ayant une activité d'inhibition des pompes d'extrusion cellulaire d'ABC (cassette de liaison à l'ATP)
  申请人：ISTITUTO TUMORI GIOVANNI PAOLO

  公开号：WO2008017588A1

  公开（公告）日：2008-02-14

  [EN] The invention relates to a new class of compounds able to inhibit in a dose-dependent manner Glycoprotein-P (P-gp) activity in cell lines in which the expression of said glycoprotein is very high, like Caco-2 (human colon cancer) cells and MCF7/Adr (adriamycin-resistant human breast carcinoma) cells. The invention also relates to the use of such compounds as medicaments useful in the treatment of states linked to the difficulty for some drugs to cross the blood-brain barrier (BBB) and generally within the context of the problems of drug resistance induced by chemotherapy agents.
  [FR] L'invention concerne une nouvelle classe de composés capables d'inhiber de manière dépendante de la dose l'activité de la glycoprotéine P (P-gp) dans des lignées cellulaires dans lesquelles l'expression de cette glycoprotéine est très élevée, par exemple les cellules Caco-2 (cancer du côlon humain) et les cellules MCF7/Adr (cancer du sein humain résistant à l'adriamycine). L'invention concerne également l'utilisation de ces composés en tant que médicaments utiles dans le traitement d'états liés à la difficulté qu'ont certaines substances médicamenteuses à franchir la barrière hémato-encéphalique (BHE) et en général dans le contexte des problèmes de la résistance aux médicaments induite par des agents chimiothérapeutiques.
• Some alkylation and Grignard reactions with 1-tetralones and related compounds
  作者：P. J. Hattersley、I. M. Lockhart、M. Wright

  DOI：10.1039/j39690000217

  日期：——

  2-monoalkyl- and 2,2-dialkyl-1-tetralones are described. Various 1-(aminoalkyl)-3,4-dihydronaphthalenes and 1-(aminoalkylidene)-1,2,3,4-tetrahydronaphthalenes have been prepared by routes involving a Grignard reaction on the appropriate 1-tetralone. Similar experiments with 4-chromanone and related compounds are reported.

  描述了产生2-单烷基-和2，2-二烷基-1-四氢萘酮的简便途径。各种1-（氨基烷基）-3，4-二氢萘和1-（氨基亚烷基）-1，2，3，4-四氢萘是通过在适当的1-四氢萘酮上进行格氏反应的方法制备的。报道了使用4-苯并二氢吡喃酮和相关化合物的类似实验。