[4-(2-methoxyphenyl)piperazin-1-yl]acetonitrile | 92043-13-5

• 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: [4-(2-methoxyphenyl)piperazin-1-yl]acetonitrile
• 英文别名: [4-(2-methoxy-phenyl)-piperazin-1-yl]-acetonitrile；2-(4-(2-Methoxyphenyl)piperazin-1-yl)acetonitrile；2-[4-(2-methoxyphenyl)piperazin-1-yl]acetonitrile
• CAS: 92043-13-5
• 化学式: C₁₃H₁₇N₃O
• mdl: MFCD01764870
• 分子量: 231.297
• InChiKey: CMNAMTJQXKKSGP-UHFFFAOYSA-N

物化性质

• 沸点：
  388.1±42.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-(2-methoxyphenyl)piperazin-1-yl]acetonitrile 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 {2-[4-(2-methoxyphenyl)piperazine-1-yl]-ethyl}carbamic acid ethyl ester
  参考文献：
  名称：

  [(4-芳基哌嗪-1-基)-烷基]-氨基甲酸乙酯衍生物作为潜在抗焦虑剂的合成和药理学评价

  摘要：

  在我们早期研究的基础上，一系列 N-{4-[4-(芳基)哌嗪-1-基]-苯基}-胺衍生物含有具有不同长度（15-20）烷基间隔基的末端氨基甲酰基片段。合成为配体，用于 5-羟色胺-1A (5-HT1A) 受体。进行分子建模研究以解释间隔长度对配体对 5-HT1A 受体的亲和力的影响。化合物 19 显示了负责识别的所有特定相互作用。配体的质子化胺与跨膜 3 螺旋 (TM3) 的带负电荷的 Asp116 形成离子氢键，而氨基甲酰基部分与 TM7 的 Asn386 和 Tyr390 相互作用。芳基参与与 Phe362 形成 CH-π 相互作用。放射性配体结合研究证实了化合物 19 与 5-HT1A 受体在对接研究中的强相互作用。化合物 19 显示出对受体的高亲和力 (Ki = 0.018 nM)。化合物 19 (3​​ mg/kg 体重) 的体内药理学测试显示开放臂进入增加，以及在 Elevated

  DOI：

  10.1007/s12272-012-0704-8
• 作为产物：
  描述：

  1-(2-甲氧苯基)哌嗪 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 生成 [4-(2-methoxyphenyl)piperazin-1-yl]acetonitrile
  参考文献：
  名称：

  N-烷基和N-芳基哌嗪的新型氰基衍生物的合成，表征和体外生物学研究。

  摘要：

  已合成了N-烷基和N-芳基哌嗪的氰基衍生物，并筛选了其抗菌和抗真菌活性。所有合成的化合物均显示出对金黄色葡萄球菌（MTCCB 737），铜绿假单胞菌（MTCCB 741），表皮链霉菌（MTCCB 1824）和大肠杆菌（MTCCB 1652）的致病菌株的抗菌活性以及对曲霉（F. 4517），黄曲霉（ITCC 5192）和黑曲霉（ITCC 5405）。所有化合物均显示轻至中度的抗菌活性。但是，化合物3c，4a和6对研究中使用的致病菌株显示出强大的抗菌活性。化合物3a，3b，4b和4d对曲霉病原菌表现出轻度至中度的抗真菌活性。使用MTT比色测定法对Hela细胞评估了该研究中报道的化合物的细胞毒性。所有化合物均显示出比对照药物庆大霉素更高的细胞生存力，其中化合物2具有最高的细胞生存力，即95％。

  DOI：

  10.1016/j.ejmech.2006.10.009

文献信息

• Phenylpiperazinylalkylamino Substituted Pyridazinones as Potent α₁ Adrenoceptor Antagonists
  作者：Daniela Barlocco、Giorgio Cignarella、Vittorio Dal Piaz、M. Paola Giovannoni、Pier G. De Benedetti、Francesca Fanelli、Federica Montesano、Elena Poggesi、Amedeo Leonardi

  DOI：10.1021/jm0009336

  日期：2001.7.1

  QSAR models have been used for designing a series of compounds characterized by a N-phenylpiperazinylalkylamino moiety linked to substituted pyridazinones, which have been synthesized. Measurements of the binding affinities of the new compounds toward the alpha (1a)-, alpha (1b)-, and alpha (1d)-AR cloned subtypes as well as the 5-HT1A receptor have been done validating, at least in part, the estimations of the theoretical models. This study provides insight into the structure activity relationships of the alpha (1)-ARs ligands and their alpha (1)-AR/5-HT1A selectivity.
• N-(4-[18F]-fluoropyridin-2-yl)-N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}carboxamides as analogs of WAY100635. New PET tracers of serotonin 5-HT1A receptors
  作者：Gonzalo García、Valentina Abet、Ramón Alajarín、Julio Álvarez-Builla、Mercedes Delgado、Luis García-García、Pablo Bascuñana-Almarcha、Carmen Peña-Salcedo、James Kelly、Miguel A. Pozo

  DOI：10.1016/j.ejmech.2014.07.096

  日期：2014.10

  N-(4-[F-18]-fluoropyridin-2-yl)-N-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}carboxamides were prepared by labeling their 4-nitropyridin-2-yl precursors through nitro substitution by the F-18 anion. In vitro and in vivo tests showed that the cyclohexanecarboxamide derivative is a reversible, selective and high affinity 5-HT1A receptor antagonist (IC50 = 0.29 nM, k(i) = 0.18 nM) with high brain uptake, slow brain clearance and stability to defluorination when compared with conventional standards. This PET radioligand is a promising candidate for an improved in vivo quantification of 5-HT1A receptors in neuropsychiatric disorders. (C) 2014 Published by Elsevier Masson SAS.
• Novel 5-HT₇ Receptor Inverse Agonists. Synthesis and Molecular Modeling of Arylpiperazine- and 1,2,3,4-Tetrahydroisoquinoline-Based Arylsulfonamides
  作者：Erik S. Vermeulen、Marjan van Smeden、Anne W. Schmidt、Jeffrey S. Sprouse、Håkan V. Wikström、Cor J. Grol

  DOI：10.1021/jm049743b

  日期：2004.10.1

  A series of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides was synthesized and evaluated for their interactions with the constitutively active 5-HT7 receptor. Effects on basal adenylate cyclase activity were measured using HEK-293 cells expressing the rat 5-HT7. All ligands produced a decrease of adenylate cyclase activity, indicative of their inverse agonism. Additionally, computational studies with a set of 22 inverse agonists, including these novel inverse agonists and inverse agonists known from literature, resulted in a pharmacophore model and a CoMFA model (R-2 = 0.97, SE = 0.18). Docking of inverse agonists at the binding site of a model of the helical parts of the 5-HT7 receptor, based on the a carbon template for 7-TM GPCRs, revealed interesting molecular interactions and a possible explanation for observed structure-activity relationships.
• 4-bromo-1-methoxy-N-[2-(4-aryl-1-piperazinyl)ethyl]-2-naphthalenecarboxamides: Selective dopamine D3 receptor partial agonists
  作者：Shelly A. Glase、Hyacinth C. Akunne、Thomas G. Heffner、Stephen J. Johnson、Suzanne R. Kesten、Robert G. MacKenzie、Peter J. Manley、Thomas A. Pugsley、Jon L. Wright、Lawrence D. Wise

  DOI：10.1016/0960-894x(96)00231-4

  日期：1996.6

  A series of 4-bromo-1-methoxy-N-[2-(4-aryl-1-piperazinyl)ethyl]-2-naphthalenecarboxamide dopamine (DA) D-3 receptor agonists has been identified. These compounds were found to be selective for DA D-3 over D-2 receptors and were shown to be partial to full agonists as measured by stimulation of mitogenesis in D-3-transfected CHO p-5 cells. Copyright (C) 1996 Elsevier Science Ltd
• Zhuang, Z.-P.; Kung, M.-P.; Mu, M., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 88 - 90
  作者：Zhuang, Z.-P.、Kung, M.-P.、Mu, M.、Kung, H. F.

  DOI：——

  日期：——