1-[2-(2-甲氧基苯氧基)乙基]哌嗪 | 117132-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-[2-(2-甲氧基苯氧基)乙基]哌嗪
• 英文名称: 4-<2-(2-methoxyphenoxy)ethyl>piperazine
• 英文别名: 1-[2-(2-methoxy-phenoxy)-ethyl]-piperazine；o-Methoxy-phenoxyethyl-piperazin；1-[2-(2-methoxyphenoxy)ethyl]piperazine
• CAS: 117132-45-3
• 化学式: C₁₃H₂₀N₂O₂
• mdl: MFCD00438753
• 分子量: 236.314
• InChiKey: XSOPYTCTNDPWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  1-[2-(2-甲氧基苯氧基)乙基]哌嗪 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 37.0h， 生成 4-chloro-2-(7-bromoheptyl)-5-<4-<2-(2-methoxyphenoxy)ethyl>-1-piprazinyl>-3(2H)-pyridazinone
  参考文献：
  名称：

  Alpha1-肾上腺素受体拮抗剂。6.哒嗪酮-芳基哌嗪的结构优化。研究对哒嗪酮环上的环状取代基和芳基哌嗪部分上的烷氧基的亲和力和选择性的影响。

  摘要：

  在继续寻找选择性的α（1）-肾上腺素能受体（AR）拮抗剂时，我们合成了新的烷氧基芳基哌嗪基烷基吡啶并嗪酮衍生物。测试了新化合物对α（1）-和α（2）-AR以及对5-HT（1A）受体的亲和力。alpha（1）-AR亲和力数据在亚纳摩尔范围内，其中3表示亲和力为0.052 nM，比哌唑嗪高约5倍。没有一个研究的化合物被发现是具有alpha（1）/ alpha（2）选择性的，但是8个化合物显示出有趣的5-HT（1A）/ alpha（1）亲和比为119。

  DOI：

  10.1021/jm0307842
• 作为产物：
  描述：

  哌嗪 、 2-(2-溴乙氧基)苯甲醚 以 乙腈 为溶剂， 生成 1-[2-(2-甲氧基苯氧基)乙基]哌嗪
  参考文献：
  名称：

  盐酸沙泊格雷酯的实用合成及其类似物的体外血小板凝集抑制活性

  摘要：

  开发了一种方便的制备盐酸沙格格雷酯的方法。设计和合成了两个系列的盐酸沙普格雷酯类似物以提高其血小板聚集抑制活性，生物学测试表明这些化合物在一定程度上具有血小板聚集抑制活性。

  DOI：

  10.1016/j.cclet.2009.11.030

文献信息

• Synthesis, &#945;-adrenoceptors affinity and &#945;1-adrenoceptor antagonistic properties of some 1,4-substituted piperazine derivatives
  作者：Marona、Kubacka、Filipek、Siwek、Dybala、Szneler、Pociecha、Gunia、Waszkielewicz, Anna M.

  DOI：10.1691/ph.2011.1543

  日期：——

  A series of different 1,4-substituted piperazine derivatives (1–11) was synthesized. It comprised 1-(substituted-phenoxyalkyl)-4-(2-methoxyphenyl)piperazine derivatives (1–5); 1,4-bis(substituted-phenoxyethyl)piperazine derivatives (6–8) and 1-(substituted-phenoxy)-3-(substituted-phenoxyalkylpiperazin-1-yl)propan-2-ol derivatives (9–11). All compounds were evaluated for affinity toward α1- and α2-receptors by radioligand binding assays on rat cerebral cortex using [3H]prazosin and [3H]clonidine as specific radioligand, respectively. Furthermore α1-antagonistic properties were checked for most promising compounds (1–5 and 10) by means of inhibition of phenylephrine induced contraction in isolated rat aorta. Antagonistic potency stayed in agreement with radioligand binding results. The most active compounds (1–5) displaced [3H]prazosin from cortical binding sites in low nanomolar range (Ki = 2.1–13.1 nM). Compound 10 showed slightly lower affinity for α1-adrenoceptor (Ki = 781 nM). Compounds 2–5 displayed the strongest antagonistic activity with pA2 values ranging from 8.441 to 8.807. Compound 1 gave a pA2 value of 7.868, while compound 10 showed the weakest antagonistic potency, giving a pA2 value of 6.374. 1-[3-(2-Chloro-6-methylphenoxy)propyl]-4-(2-methoxyphenyl)piperazine hydrochloride (5) showed the best α1- affinity properties with a Ki(α1) value of 2.1 nM and it was 61.05 fold more selective toward α1 than α2-receptors. The best properties showed 1-[3-(2,6-dimethylphenoxy)propyl]-4-(2-methoxyphenyl)piperazine hydrochloride (4) with a Ki(α1) value of 2.4 nM, a 142.13 fold better selectivity to α1- over α2-adrenoceptors and the best antagonistic potency (pA2 = 8.807). It is worth to emphasized that all most promising compounds possessed an 1-(o-methoxyphenyl)piperazine moiety which probably plays an important role in the affinity to α-adrenoceptors.

  合成了一系列不同的 1,4 取代哌嗪衍生物 (1-11)。其中包括 1-（取代的苯氧基烷基）-4-（2-甲氧基苯基）哌嗪衍生物（1-5）、1,4-双（取代的苯氧基乙基）哌嗪衍生物（6-8）和 1-（取代的苯氧基）-3-（取代的苯氧基烷基哌嗪-1-基）丙-2-醇衍生物（9-11）。通过在大鼠大脑皮层分别使用[3H]哌唑嗪和[3H]氯尼丁作为特异性放射性配体进行放射性配体结合试验，评估了所有化合物对α1-和α2-受体的亲和力。此外，通过抑制离体大鼠主动脉中由苯肾上腺素引起的收缩，检测了最有希望的化合物（1-5 和 10）的α1-拮抗特性。拮抗效力与放射性配体结合结果保持一致。活性最强的化合物（1-5）在低纳摩尔范围内（Ki = 2.1-13.1 nM）将[3H]哌唑嗪从皮质结合位点移出。化合物 10 对 α1 肾上腺素受体的亲和力稍低（Ki = 781 nM）。化合物 2-5 显示出最强的拮抗活性，pA2 值在 8.441 到 8.807 之间。化合物 1 的 pA2 值为 7.868，而化合物 10 的拮抗效力最弱，pA2 值为 6.374。1-[3-(2- 氯-6-甲基苯氧基)丙基]-4-(2-甲氧基苯基)哌嗪盐酸盐（5）显示出最佳的 α1 亲和性，Ki(α1) 值为 2.1 nM，它对α1 受体的选择性比对α2 受体的选择性高 61.05 倍。性能最好的是 1-[3-(2,6-二甲基苯氧基)丙基]-4-(2-甲氧基苯基)哌嗪盐酸盐（4），其 Ki(α1) 值为 2.4 nM，对α1-的选择性比对α2-肾上腺素受体的选择性高 142.13 倍，拮抗效力最好（pA2 = 8.807）。值得强调的是，所有最有前途的化合物都具有 1-（邻甲氧基苯基）哌嗪分子，这可能对α-肾上腺素受体的亲和力起着重要作用。
• Chemical mechanical planarization for tungsten-containing substrates
  申请人：AIR PRODUCTS AND CHEMICALS, INC.

  公开号：EP2779217A2

  公开（公告）日：2014-09-17

  Chemical mechanical polishing (CMP) compositions for polishing tungsten or tungsten-containing substrates comprise an abrasive, at least one solid catalyst, a chemical additive selected from the groups consisting of piperazine derivatives, salts of cyanate, and combinations thereof; and a liquid carrier. Systems and processes use the aqueous formulations for polishing tungsten or tungsten-containing substrates.

  用于抛光钨或含钨基材的化学机械抛光（CMP）组合物包括磨料、至少一种固体催化剂、一种选自哌嗪衍生物、氰酸盐及其组合的化学添加剂；以及一种液体载体。系统和工艺使用水性制剂抛光钨或含钨基材。
• α1-Adrenoceptor antagonists. 5. Pyridazinone-arylpiperazines. Probing the influence on affinity and selectivity of both ortho-Alkoxy groups at the arylpiperazine moiety and cyclic substituents at the pyridazinone nucleus
  作者：Laura Betti、Monia Floridi、Gino Giannaccini、Fabrizio Manetti、Giovannella Strappaghetti、Andrea Tafi、Maurizio Botta

  DOI：10.1016/s0960-894x(02)00932-0

  日期：2003.1

  Our previous work on pyridazinone-arylpiperazine derivatives suggested some structural features that a compound should have to show high affinity and good selectivity for alpha(1) adrenoceptors (AR) with respect to alpha(2)-AR. Accordingly, two classes of new alkoxyphenylpiperazinylheptylpyridazinones were designed and synthesized to evaluate the effect of the alkoxy substituent on affinity and selectivity. As expected, affinity increased with larger alkoxy groups. Affinity values are all comparable with that of the reference compound (prazosin), with the exception of compound 1c found 4.5-fold more active than prazosin. (C) 2002 Elsevier Science Ltd. All rights reserved.
• DIHYDROPYRIDINE CALCIUM ANTAGONIST COMPOUNDS, PREPARATION METHODS AND MEDICAL USES THEREOF
  申请人：Cosunter Pharmaceutical Company

  公开号：EP2251337B1

  公开（公告）日：2013-11-20
• Novel and highly selective postsynaptic α-adrenoreceptor antagonists: synthesis and structure-activity relationships of alkane-bridged [4-(phenoxyethyl)-1-piperazinyl]-3(2H)-pyridazinones
  作者：S Corsano、R Scapicchi、G Strappaghetti、G Marucci、F Paparelli

  DOI：10.1016/0223-5234(96)88211-0

  日期：1995.1

  The synthesis of selected 4-[4-(phenoxyethyl)-1-piperazinyl]-3(2H)-pyridazinones and alkane-bridged dimers of 4-, 5- and 6-[4-(phenoxyethyl)-1-piperazinyl]-3(2H)-pyridazinones is reported, The blocking activity of these compounds was determined on the pre- and postsynaptic a-adrenoreceptors of isolated rat vas deferens.