1-(4-(4-cyclohexylpiperazin-1-yl)butyl)-1H-indole | 1121931-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(4-(4-cyclohexylpiperazin-1-yl)butyl)-1H-indole
• 英文别名: 1-(4-(4-cyclohexylpiperazin-1-yl)butyl)indole；1-[4-(4-Cyclohexylpiperazin-1-yl)butyl]indole
• CAS: 1121931-12-1
• 化学式: C₂₂H₃₃N₃
• 分子量: 339.524
• InChiKey: QTVZKXTYXRRYBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  11.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 在 四丁基碘化铵 、 potassium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-(4-(4-cyclohexylpiperazin-1-yl)butyl)-1H-indole
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of indole-based sigma receptor ligands

  摘要：

  A series of novel indole-based analogs were prepared and their affinities for sigma receptors were determined using in vitro radioligand binding assays. The results of this study identified several compounds with nanomolar sigma-2 affinity and significant selectivity over sigma-1 receptors. In particular, 2-(4-(3-(4-fluorophenyl)indol-1-yl)butyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (9f) was found to display high affinity at sigma-2 receptors with good selectivity (sigma-1/sigma-2 = 395). The pharmacological binding profile for this compound was established with other relevant non-sigma sites. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.031

文献信息

• HIGHLY SELECTIVE SIGMA RECEPTOR RADIOLIGANDS
  申请人：McCurdy Christopher R.

  公开号：US20110280804A1

  公开（公告）日：2011-11-17

  Compounds having the general formula III′, or IV′ wherein R 1 can be a radical of an optionally substituted C-4 to C-7 N-containing heterocycle or a radical of an optionally substituted cyclic or acyclic tertiary amine or isoindoline-1,3-dione: R 2,4,5,6 can each independently be any one or combinations of the following moieties, cyano, nitro, acyl, alkyl, amido, azido, isothiocyanate, isocyanate, optionally substituted anilino, halogens, ethers, sulfonamides, thioacyl, nitro, aromatic, heterocyclic, olefinic, acetylene, deuterium, or tritium; Y is S; Z can be either H, O, S, S—R or NR where R groups can be either H, aryls, alkyls, or cycloalkyls; “n” can be 1 to 5 carbons in length and stereoisomers, functional analogs, and pharmaceutically acceptable salts thereof and wherein the moiety bridging R 1 and N can be a substituted alkylene, optionally substituted alkenylene or optionally substituted alkynylene and where the alkylene group can include an inserted C 3 -C 5 cycloalkyl group, aromatic, and heterocyclic group; and wherein X is C 1 -C 4 radiohaloalkyl.

  具有通式III'或IV'的化合物，其中R1可以是一个可选取代的C-4到C-7含氮杂环的基团，或者是一个可选取代的环状或非环状三级胺或异吲哚啉-1,3-二酮的基团；R2、4、5、6可以各自独立地是以下任何一种或组合：氰基、硝基、酰基、烷基、酰胺基、偶氮基、异硫氰酸酯基、异氰酸酯基、可选取代的苯胺基、卤素、醚、磺酰胺基、硫代酰基、芳香族、杂环、烯烃、乙炔、氘或氚；Y是S；Z可以是H、O、S、S-R或NR，其中R基团可以是H、芳基、烷基或环烷基；“n”可以是1到5个碳原子，包括立体异构体、功能类似物和药物可接受的盐；其中桥接R1和N的基团可以是取代的烷基、可选取代的烯基或可选取代的炔基，其中烷基可以包括插入的C3-C5环烷基、芳香族和杂环基团；X为C1-C4放射性卤代烷基。
• HIGHLY SELECTIVE SIGMA RECEPTOR LIGANDS AND RADIOLIGANDS AS PROBES IN NOCICEPTIVE PROCESSING AND THE PATHPHYSIOLOGICAL STUDY OF MEMORY DEFICITS AND COGNITIVE DISORDERS
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20140328755A1

  公开（公告）日：2014-11-06

  A method for localizing and quantifying S1R role in nociceptive processing; for providing a guide to providing an analgesic therapy; of using an S1R selective ligand as a biomarker for pathphysiological study of memory deficits and cognitive disorders; or of detecting increased S1R density at the site of nerve injury arising from neuropathic pain comprising using as a probe at least one SR1 selective compound or radioligand of the general formula III′, or IV′:

  一种定位和量化S1R在伤害处理中的作用的方法；为提供镇痛疗法提供指导；使用S1R选择性配体作为记忆缺陷和认知障碍的病理生理研究的生物标志物；或者使用至少一种SR1选择性化合物或放射性配体作为探针，检测神经病理性疼痛引起的神经损伤部位的S1R密度增加，其化学结构为通式III'或IV'。
• USE OF BENZO FIVE-MEMBERED NITROGEN HETEROCYCLIC PIPERAZINE OR PIPERIDINE DERIVATIVES
  申请人：LIAONING EMMY BIOLOGICAL PHARMACEUTICAL CO., LTD.

  公开号：US20150297586A1

  公开（公告）日：2015-10-22

  This invention relates to the use of a compound in formula (I) and its salts acceptable pharmaceutically in preparation of vasodilative drugs: Wherein, R 1 , R 2 , X, Y, A and B are defined in the invention.

  本发明涉及使用式(I)中的化合物及其在制备扩血管药物时可接受的药用盐：其中，R1、R2、X、Y、A和B在本发明中有定义。
• Multifunctional thiosemicarbazones and deconstructed analogues as a strategy to study the involvement of metal chelation, Sigma-2 (σ2) receptor and P-gp protein in the cytotoxic action: In vitro and in vivo activity in pancreatic tumors
  作者：Maria Laura Pati、Mauro Niso、Dirk Spitzer、Francesco Berardi、Marialessandra Contino、Chiara Riganti、William G. Hawkins、Carmen Abate

  DOI：10.1016/j.ejmech.2017.12.024

  日期：2018.1

  The aggressiveness of pancreatic cancer urgently requires more efficient treatment options. Because the sigma-2 (sigma(2)) receptor was recently proposed as a promising target for pancreatic cancer therapy, we explored our previously developed multifunctional thiosemicarbazones, designed to synergistically impair cell energy levels, by targeting sigma(2) and P-gp proteins and chelating Iron. A deconstruction approach was herein applied by removing one function at a time from the potent multifunctional thiosemicarbazones 1 and 2, to investigate the contribution to cytotoxicity of each target involved. The results from in vitro (panel of pancreatic tumor cells) and in vivo experiments (C57BL/6 bearing KP02 tumor), suggest that while the multifunctional activity was not required for the antitumor activity of these thiosemicarbazones, sigma(2)-targeting appeared to allow alternative tumor cell death mechanisms, leading to potent and less toxic off-targets toxicities compared to other thiosemicarbazones devoid of sigma(2)-targeting. (C) 2017 Elsevier Masson SAS. All rights reserved.
• HIGHLY SELECTIVE SIGMA 1 RECEPTOR LIGANDS AND RADIOLIGANDS AS PROBES IN NOCICEPTIVE PROCESSING AND THE PATHOPHYSIOLOGICAL STUDY OF MEMORY DEFICITS AND COGNITIVE DISORDERS
  申请人：The University Of Mississippi

  公开号：EP3102204B1

  公开（公告）日：2021-05-05