1-(苯并[b]呋喃-7-基)哌嗪盐酸盐 | 115464-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(苯并[b]呋喃-7-基)哌嗪盐酸盐
• 英文名称: 1-(benzofuran-7-yl)piperazine hydrochloride
• 英文别名: 1-(7-benzofuranyl)piperazine hydrochloride；1-(benzofuran-7-yl)piperazine hydrochloride；1-(7-benzofuranyl)piperazine hydrochloride；1-benzo[b]furan-7-yl-piperazine HCl；1-(Benzo[b]furan-7-yl)-piperazine hydrochloride；1-(1-benzofuran-7-yl)piperazine;hydrochloride
• CAS: 115464-81-8
• 化学式: C₁₂H₁₄N₂O*ClH
• 分子量: 238.717
• InChiKey: MVAODIOCPQCJKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(苯并[b]呋喃-7-基)哌嗪盐酸盐 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 1-(1-苯并呋喃-7-基)哌嗪
  参考文献：
  名称：

  ARYLPIPERAZINYL-CYCLOHEXYL INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION

  摘要：

  公开号：

  EP1147083B1
• 作为产物：
  描述：

  3-硝基水杨醛 在 镍 盐酸 、 氢氧化钾 、 四丁基溴化铵 、 potassium carbonate 、 一水合肼 、 copper(II) oxide 作用下， 以 喹啉 、 甲醇 、 乙醇 、 氯苯 、 甲苯 为溶剂， 反应 94.5h， 生成 1-(苯并[b]呋喃-7-基)哌嗪盐酸盐
  参考文献：
  名称：

  2-苯基吡咯作为构象受限的苯甲酰胺类似物。一类新的潜在抗精神病药。2。

  摘要：

  合成了一系列2-苯基吡咯曼尼希碱，并在药理模型中筛选了抗精神病活性和锥体束外作用。5-（4-氟苯基）-2-[[4-（2-甲氧基苯基）-1-哌嗪基]甲基]吡咯的结构修饰（1），是新型的钠依赖性非典型多巴胺D-2拮抗剂的原型，产生2-[[[4-（7-苯并呋喃基）-1-哌嗪基]甲基] -5-（4-氟苯基）吡咯（15），它是比母体化合物更有效和选择性的D-2拮抗剂。阿朴吗啡诱导的攀爬行为具有出色的口服活性，并且有条件的回避反应测试以及没有僵住症，使得该化合物作为潜在的抗精神病药特别有前景，且诱发急性锥体外系副作用的可能性低。

  DOI：

  10.1021/jm00118a011

文献信息

• Method of treating psychotropic conditions employing substituted
  申请人：Duphar International Research B.V.

  公开号：US04782061A1

  公开（公告）日：1988-11-01

  The invention relates to a group of new bicyclic heteroarylpiperazine derivatives of formula 1. It was found that these compounds have interesting psychotropic in particular anti-psychotic properties. The compounds can be prepared according to methods known for the synthesis of analogous compounds.

  本发明涉及公式1的一组新的双环杂芳基哌嗪衍生物。发现这些化合物具有有趣的精神药理学特性，特别是抗精神病药物特性。这些化合物可以按照合成类似化合物的已知方法制备。
• New pharmaceutical compositions having anti-psychotic properties
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0190472A1

  公开（公告）日：1986-08-13

  The invention relates to a group of new bicyclic hetero- srylpiperazine derivatives of formula 1. It was found that these compounds have interesting psychotropic in particular anti-psychotic properties. The compounds can be prepared according to methods known for the synthesis of analogous compounds.

  本发明涉及一组新的式 1 双环杂芳基哌嗪衍生物。研究发现，这些化合物具有有趣的精神药物特性，尤其是抗精神病特性。 这些化合物可以按照合成类似化合物的已知方法制备。
• Structure-Affinity Relationship Studies on 5-HT1A receptor Ligands. 2. Heterobicyclic Phenylpiperazines with N4-Aralkyl Substituents
  作者：Bart J. van Steen、Ineke van Wijngaarden、Martin Th. M. Tulp、Willem Soudijn

  DOI：10.1021/jm00043a015

  日期：1994.8

  Structure-affinity relationship (SAR) studies for the 5HT(1A) receptor site are presented for two series of heterobicyclic phenylpiperazines with N4-aralkyl substituents: 4-aralkyl derivatives of 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine (3) and 1-(benzo[b]furan-7-yl)piperazine (4). Their affinities far 5-HT1A receptors range from 0.15 to 28 nM and thus emphasize the importance of N4-substitution. By combining the SAR of these N4-aralkyl series with the recently published(11) SAR of the N4-alkyl-substituted phenylpiperazines, the nature of the interaction of the N4-substituted phenylpiperazines and the 5-HT1A receptor was further examined using comparative molecular field analysis (CoMFA). To discriminate between two postulated hypotheses, CoMFA models were built and validated utilizing cross-validation, bootstrapping, and randomizing techniques. The model based on a N4-substituent alignment in which all N4-substituents are equally oriented in space was selected for further evaluation. According to the CoMFA/PLS analysis, the steric and electrostatic field properties contribute in a 98:2 ratio to the affinity found for the 5HT(1A) receptor. Increasing steric bulk was found to be positively as well as negatively related to affinity depending on the distance of the bulk's center from the N4-nitrogen. The location of these steric CoMFA contour levels are well defined in space when the defined alignment rules are followed. Because CoMFA does not take hydrogen bonding into account, this could indicate that the contribution of the amide function (its ability to interact through hydrogen bonding), as present in the N4-substituents, to affinity is of minor importance.
• Structure-affinity relationship studies on 5-HT1A receptor ligands. 1. Heterobicyclic phenylpiperazines with N4-alkyl substituents
  作者：Bart J. van Steen、Ineke van Wijngaarden、Martin T. M. Tulp、Willem Soudijn

  DOI：10.1021/jm00071a006

  日期：1993.9

  Structure-affinity relationship (SAR) studies for 5-HT1A receptor site are presented for two series of heterobicyclic phenylpiperazines with N4-alkyl substituents: 4-alkyl derivatives of 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine (3) and 1-(benzo[b]furan-7-yl)piperazine (4). The linear and branched hydrocarbon chain derivatives up to n-decyl were synthesized and evaluated for their ability to displace [H-3]-2-(di-n-propylamino)-8-hydroxytetralin from its specific binding sites in rat frontal cortex homogenates. All compounds displayed a nanomolar affinity for the 5-HT1A receptor. In both series the N-ethyl and N-n-propyl substituted derivatives have similar affinities, being slightly but statistically significantly less active than the N-methyl-substituted derivatives. Elongation of the hydrocarbon chain increases the affinity for the central 5-HT1A receptor site, reaching a local maximum for the N-n-hexyl-substituted phenylpiperazines 23 (K(i) = 0.50 nM) and 39 (K(i) = 0.54 nM). Assuming that the arylpiperazine derivatives at the 5-HT1A binding site are in the ionic state, ionization constants were determined in order to evaluate the use of the local inhibition constant, K(i)+, as a more convenient parameter to study the structure-affinity relationships. However, the K(i)+ could not account for the specific N4-substituent effects found.
• J. Med. Chem. 1988, 31, 1934-1940
  作者：

  DOI：——

  日期：——