4-(3-bromo-n-propyl)-4,5,6,7-tetrahydrobenzothiophene | 161923-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4-(3-bromo-n-propyl)-4,5,6,7-tetrahydrobenzothiophene
• 英文别名: 4-(3-Bromopropyl)-4,5,6,7-tetrahydro-1-benzothiophene
• CAS: 161923-66-6
• 化学式: C₁₁H₁₅BrS
• 分子量: 259.21
• InChiKey: SASCNUPMXYBQNU-UHFFFAOYSA-N

物化性质

• 沸点：
  330.5±22.0 °C(predicted)
• 密度：
  1.343±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(3-bromo-n-propyl)-4,5,6,7-tetrahydrobenzothiophene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 以26%的产率得到4-(3-bromopropyl)-1-benzothiophene
  参考文献：
  名称：

  Synthesis and binding assays of novel 3,3-dimethylpiperidine derivatives with various lipophilicities as σ1 receptor ligands

  摘要：

  Starting from two carbocyclic analogs, a series of 3,3-dimethylpiperidine derivatives was prepared and tested in radioligand binding assays at sigma(1) and sigma(2) receptors, and at Delta(8)-Delta(7) sterol isomerase (SI) site. The novel compounds mostly bear heterocyclic rings or bicyclic nucleus of differing lipophilicities. Compounds 18a and 19a,b demonstrated the highest sigma(1) affinity (K-i = 0.14-0.38 nM) with a good selectivity versus sigma(2) binding. Among them, 18a had the lowest C log D value (3.01) and only 19b was selective versus SI too. Generally, it was observed that more planar and hydrophilic heteronuclei conferred a decrease in affinity for both sigma receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.023
• 作为产物：
  描述：

  4,5,6,7-四氢-4-苯并噻吩 、 溴代环丙烷 在 magnesium 作用下， 生成 4-(3-bromo-n-propyl)-4,5,6,7-tetrahydrobenzothiophene
  参考文献：
  名称：

  Synthesis and binding assays of novel 3,3-dimethylpiperidine derivatives with various lipophilicities as σ1 receptor ligands

  摘要：

  Starting from two carbocyclic analogs, a series of 3,3-dimethylpiperidine derivatives was prepared and tested in radioligand binding assays at sigma(1) and sigma(2) receptors, and at Delta(8)-Delta(7) sterol isomerase (SI) site. The novel compounds mostly bear heterocyclic rings or bicyclic nucleus of differing lipophilicities. Compounds 18a and 19a,b demonstrated the highest sigma(1) affinity (K-i = 0.14-0.38 nM) with a good selectivity versus sigma(2) binding. Among them, 18a had the lowest C log D value (3.01) and only 19b was selective versus SI too. Generally, it was observed that more planar and hydrophilic heteronuclei conferred a decrease in affinity for both sigma receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.023

文献信息

• Novel Potent σ₁ Ligands:  <i>N</i>-[ω-(Tetralin-1-yl)alkyl]piperidine Derivatives
  作者：Francesco Berardi、Giuseppe Giudice、Roberto Perrone、Vincenzo Tortorella、Stefano Govoni、Laura Lucchi

  DOI：10.1021/jm9508898

  日期：1996.1.1

  N-[(tetralin-1-yl)alkyl]piperidines and a number of related N-di-n-propyl-[(tetralin-1-yl)alkyl]amines were prepared. Structural modifications such as piperidine substitutions, intermediate chain lengthening, and the nature of the aromatic ring were explored in order to identify structural requirements for selective sigma 1 affinity. They were tested in radioligand binding assays on sigma 1, 5-HT1A and 5-HT2

  制备了一系列取代的N-[（四氢-1-基）烷基]哌啶和许多相关的N-二-正丙基-[（四氢-1-基）烷基]胺。为了确定选择性sigma 1亲和力的结构要求，对诸如哌啶取代，中间链加长和芳环性质等结构修饰进行了研究。在放射性配体结合测定中对它们进行了测试，其中包括sigma 1、5-HT1A和5-HT2血清素能，PCP（苯环利定）和D-2多巴胺能受体。此处报道的几乎所有化合物均显示出高至超强的sigma 1亲和力，并且某些化合物还表现出比其他受体广泛的选择性。在[3H]-（+）-戊唑啉结合中，3,3-二甲基-1- [3-（5-甲氧基-1,2,3,4-四氢萘-1-基）-正丙基]哌啶（24 ）和3,3-二甲基-1- [4-（1,2,3，4-四氢萘-1-基）正丁基哌啶（26）达到最低的Ki值（分别为0.4和0.8 nM）。化合物24还表现出相当大的PCP亲和力（Ki = 34.2 nM），而化合物26
• High Affinity and Selectivity on 5-HT1A Receptor of 1-Aryl-4-[(1-tetralin)alkyl]piperazines. 2
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Marcello Leopoldo、Vincenzo Tortorella、Francesco Fiorentini、Vincenzo Olgiati、Alberto Ghiglieri、Stefano Govoni

  DOI：10.1021/jm00006a013

  日期：1995.3

  in order to increase the selectivity on the 5-HT1A versus D-2, alpha 1, sigma, and other 5-HT receptors. Many changes have been effected on previous structures of type 3(1-aryl-4-[3-(1,2-dihydronaphthalen-4-yl)-n-propyl]piperazines). Several synthetic procedures were followed to obtain the final products, depending on the presence or absence of a double bond, as well as of a heteroatom on the side chain

  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。