1-chroman-5-yl-piperazine | 105685-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-chroman-5-yl-piperazine
• 英文别名: 1-(3,4-dihydro-2H-chromen-5-yl)piperazine
• CAS: 105685-39-0
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: MEIFUSPWFWXMBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chroman-5-yl-piperazine 、 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 7-[4-(4-chroman-5-ylpiperazin-1-yl)butoxy]-3,4-dihydro-1H-[1,8]naphthyridin-2-one
  参考文献：
  名称：

  Discovery of PF-00217830: Aryl piperazine napthyridinones as D2 partial agonists for schizophrenia and bipolar disorder

  摘要：

  The synthesis and structure-activity relationship (SAR) of a novel series of aryl piperazine napthyridinone D-2 partial agonists is described. Our goal was to optimize the affinities for the D-2, 5-HT2A and 5-HT1A receptors, such that the D-2/5-HT2A ratio was greater than 5 to ensure maximal occupancy of these receptors when the D-2 occupancy reached efficacious levels. This strategy led to identification of PF-00217830 (2) with robust inhibition of sLMA (MED = 0.3 mg/kg) and DOI-induced head twitches in rats (31% and 78% at 0.3 and 1 mg/kg) with no catalepsy observed at the highest dose tested (10 mg/kg). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.059
• 作为产物：
  描述：

  3-nitro-2-vinylphenol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium on activated charcoal 氢气 、 potassium carbonate 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 氯苯 、 丙酮 、 正己醇 为溶剂， 反应 28.1h， 生成 1-chroman-5-yl-piperazine
  参考文献：
  名称：

  Synthesis of chromanyl and dihydrobenzofuranyl piperazines

  摘要：

  The synthesis of a series of regioisomeric chromanyl and dihydrobenzofuranyl piperazines is described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.02.121

文献信息

• [1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia
  申请人：Clark D. Jerry

  公开号：US20050043309A1

  公开（公告）日：2005-02-24

  This invention relates to compounds of the formula 1 wherein G, D, A, Z, Q, X, Y, R 1 , and R 4 through R 7 are defined as in the specification, processes for preparing the same and intermediates used in making the same, and pharmaceutical compositions containing such compounds and their use in the treatment of central nervous system disorders and other disorders.

  这项发明涉及公式1的化合物 其中G、D、A、Z、Q、X、Y、R 1 和R 4 至R 7 的定义如规范中所述，制备这些化合物的方法以及用于制备这些化合物的中间体，以及含有这些化合物的药物组合物及其在治疗中枢神经系统疾病和其他疾病中的用途。
• Synthesis, Structure−Activity Relationships, and Biological Properties of 1-Heteroaryl-4-[ω-(1<i>H</i>-indol-3-yl)alkyl]piperazines, Novel Potential Antipsychotics Combining Potent Dopamine D₂ Receptor Antagonism with Potent Serotonin Reuptake Inhibition
  作者：Pieter Smid、Hein K. A. C. Coolen、Hiskias G. Keizer、Rolf van Hes、Jan-Peter de Moes、Arnold P. den Hartog、Bob Stork、Rob H. Plekkenpol、Leonarda C. Niemann、Cees N. J. Stroomer、Martin Th. M. Tulp、Herman H. van Stuivenberg、Andrew C. McCreary、Mayke B. Hesselink、Arnoud H. J. Herremans、Chris G. Kruse

  DOI：10.1021/jm050148z

  日期：2005.11.1

  A series of novel bicyclic 1-heteroaryl-4-[omega-(1H-indol-3-yl)alkyl]piperazines was synthesized and evaluated on binding to dopamine D(2) receptors and serotonin reuptake sites. This class of compounds proved to be potent in vitro dopamine D(2) receptor antagonists and in addition were highly active as serotonin reuptake inhibitors. Some key representatives showed potent pharmacological in vivo activities

  合成了一系列新颖的双环1-杂芳基-4- [ω-（1H-吲哚-3-基）烷基]哌嗪，并评估了与多巴胺D（2）受体和5-羟色胺再摄取位点的结合。这类化合物被证明是有效的体外多巴胺D（2）受体拮抗剂，此外还具有作为5-羟色胺再摄取抑制剂的高活性。一些主要代表在口服阿扑吗啡诱导的爬升的拮抗作用和5-HTP诱导的小鼠行为的拮抗作用中均显示出口服给药后体内的有效药理活性。根据临床前数据，8- 4- [3-（5-氟-1H-吲哚-3-基）丙基]哌嗪-1-基} -4H-苯并[1,4]恶嗪-（R选择）-2-甲基-3-酮（45c，SLV314）进行临床开发。体外和体内研究表明45c具有良好的药代动力学特性和较高的CNS血浆比例。
• Benzdioxane piperazine derivatives with a combination of affinity for dopamine-D2 receptors and serotonin reuptake sites
  申请人：Hes van Roelof

  公开号：US20060122175A1

  公开（公告）日：2006-06-08

  The present invention relates to a group of novel 3-(2-piperidin-4-yl-ethyl)-1H-indole derivatives with a dual mode of action: serotonin reuptake inhibition and affinity for dopamine-D 2 receptors and to methods for the preparation of these compounds. The invention also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. The compounds have the general formula (1) wherein the symbols have the meanings given in the specification.

  本发明涉及一组新型3-(2-哌啶-4-基乙基)-1H-吲哚衍生物，具有双重作用方式：抑制5-羟色胺再摄取和对多巴胺-D2受体的亲和力，并涉及制备这些化合物的方法。该发明还涉及利用本文所披露的化合物制造具有有益效果的药物。这些化合物具有一般式（1），其中符号的含义如规范中所述。
• [EN] [1,8]NAPHTHYRIDIN-2-ONES AND RELATED COMPOUNDS FOR THE TREATMENT OF SCHIZOPHRENIA<br/>[FR] [1,8]NAPHTYRIDIN-2-ONES ET COMPOSES APPARENTES DESTINES AU TRAITEMENT DE LA SCHIZOPHRENIE
  申请人：WARNER LAMBERT CO

  公开号：WO2005019215A1

  公开（公告）日：2005-03-03

  This invention relates to compounds of the Formula (1) wherein G, A, Z, Q, X, Y, and R1 and R2 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.

  本发明涉及式（1）的化合物，其中G，A，Z，Q，X，Y和R1和R2如规范中所定义，包含它们的制药组合物以及它们在治疗中枢神经系统和其他疾病中的应用。
• [1,8]NAPHTHYRIDIN-2-ONES AND RELATED COMPOUNDS FOR THE TREATMENT OF SCHIZOPHRENIA
  申请人：Clark D. Jerry

  公开号：US20060287310A1

  公开（公告）日：2006-12-21

  This invention relates to compounds of the formula 1 wherein G, D, A, Z, Q, X, Y, R 1 , and R 4 through R 7 are defined as in the specification, processes for preparing the same and intermediates used in making the same, and pharmaceutical compositions containing such compounds and their use in the treatment of central nervous system disorders and other disorders.

  本发明涉及式1的化合物，其中G、D、A、Z、Q、X、Y、R1和R4至R7如规范中所定义，制备该化合物的过程以及用于制备该化合物的中间体，以及含有该化合物的制药组合物及其在治疗中枢神经系统疾病和其他疾病中的应用。