3-[2-(4-Cyclohexylpiperazin-1-yl)ethyl]-1,3-benzoxazol-2-one | 1016539-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 3-[2-(4-Cyclohexylpiperazin-1-yl)ethyl]-1,3-benzoxazol-2-one
• CAS: 1016539-22-2
• 化学式: C₁₉H₂₇N₃O₂
• 分子量: 329.442
• InChiKey: CKIRCWNMBOKGBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  36
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-环己基哌嗪 、 3-(2-溴乙基)-1,3-苯并噁唑-2(3H)-酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以49%的产率得到3-[2-(4-Cyclohexylpiperazin-1-yl)ethyl]-1,3-benzoxazol-2-one
  参考文献：
  名称：

  Conversion of a Highly Selective Sigma-1 Receptor–Ligand to Sigma-2 Receptor Preferring Ligands with Anticocaine Activity

  摘要：

  Cocaine's toxicity can be mitigated by blocking its interaction with sigma-1 receptors. The involvement of sigma-2 receptors remains unclear. To investigate their potential role, we have designed compounds through a convergent synthesis utilizing a highly selective sigma-1 ligand and elements of a selective sigma-2 ligand. Among the synthesized compounds was produced a subnanomolar sigma-2 ligand with an 11-fold preference over sigma-1 receptors. These compounds may be useful in developing effective pharmacotherapies for cocaine toxicity.

  DOI：

  10.1021/jm701357m

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'。
• [EN] HIGHLY SELECTIVE SIGMA RECEPTOR LIGANDS<br/>[FR] LIGANDS DE RÉCEPTEUR SIGMA HAUTEMENT SÉLECTIFS
  申请人：UNIV MISSISSIPPI

  公开号：WO2009026227A3

  公开（公告）日：2009-04-09
• 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
• HIGHLY SELECTIVE SIGMA RECEPTOR LIGANDS
  申请人：McCurdy Christopher R.

  公开号：US20100329978A1

  公开（公告）日：2010-12-30

  Compounds having the general formula II, 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 2,3,4,5,6 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 can be either CH, CH 2 , O, S, OCH 2 , N—R, N—Ar, C—R, C—Ar; Z can be either H, O, S, S—R or NR. 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 hetercocyclic group; wherein X′ is halogen, or C 1 -C 4 haloalyl; wherein the R x is a C 1 -C 5 straight chain or branched chain alkyl or a C 1 -C 4 straight chain or branched chain haloalkyl.