2-(benzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole | 959698-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-(benzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole
• 英文别名: 2-Benzylsulfanyl-5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3,4-oxadiazole
• CAS: 959698-04-5
• 化学式: C₁₇H₁₄N₂O₃S
• 分子量: 326.376
• InChiKey: JMRMEWXQQQSRHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-二氢-1,4-苯并二噁烷-6-羧酸 在 硫酸 、 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 2-(benzylthio)-5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, biological evaluation, and molecular docking studies of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan moiety as potential anticancer agents

  摘要：

  In present study, a series of new 1,3,4-oxadiazole derivatives containing 1,4-benzodioxan moiety (6a-6s) as potential telomerase inhibitors were synthesized. The bioassay tests demonstrated that compounds 6k, 6l, 6m, 6n and 6s exhibited broad-spectrum antitumor activity with IC50 concentration range from 7.21 mu M to 25.87 mu M against the four cancer cell lines, HEPG2, HELA, SW1116 and BGC823. Moreover, all the title compounds were assayed for telomerase inhibition using the TRAP-PCR-ELISA assay. The results showed compound 6k possessed the most potent telomerase activity (IC50 = 1.27 +/- 0.05 mu M). Docking simulation was performed to position compound 6k into the active site of telomerase (3DU6) to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.013

文献信息

• NOVEL 1,4-DIAZA-BICYCLO[3.2.2]NONYL OXADIAZOLYL DERIVATIVES AND THEIR MEDICAL USE
  申请人：Peters Dan

  公开号：US20090118266A1

  公开（公告）日：2009-05-07

  This invention relates to novel 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyl derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  本发明涉及新型1,4-二氮杂双环[3.2.2]壬基噁二唑衍生物及其用于制造药物组合物。本发明的化合物被发现是乙酰胆碱受体的胆碱能配体。由于它们的药理特性，本发明的化合物可能对治疗与中枢神经系统（CNS）和外周神经系统（PNS）的胆碱能系统有关的疾病或疾病，平滑肌收缩有关的疾病或疾病，内分泌疾病或疾病，神经退行性疾病或疾病，炎症、疼痛以及由于滥用化学物质的终止而引起的戒断症状可能有用。
• 1,4-DIAZA-BICYCLO[3.2.2]NONYL OXADIAZOLYL DERIVATIVES AND THEIR MEDICAL USE
  申请人：Peters Dan

  公开号：US20100317654A1

  公开（公告）日：2010-12-16

  This invention relates to novel 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyl derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  本发明涉及新型1,4-二氮杂双环[3.2.2]壬基噁唑基衍生物及其在制造药物组合物方面的应用。本发明中的化合物被发现是胆碱能受体的烟碱酸乙酰胆碱受体配体。由于它们的药理特性，本发明中的化合物可能对治疗与中枢神经系统（CNS）和周围神经系统（PNS）的胆碱能系统相关的疾病或障碍，平滑肌收缩相关的疾病或障碍，内分泌疾病或障碍，神经退行性疾病或障碍，炎症相关的疾病或障碍，疼痛和化学物质滥用终止引起的戒断症状等疾病或障碍有用。
• US7807667B2
  申请人：——

  公开号：US7807667B2

  公开（公告）日：2010-10-05
• US8101598B2
  申请人：——

  公开号：US8101598B2

  公开（公告）日：2012-01-24
• [EN] NOVEL 1,4-DIAZA-BICYCLO[3.2.2]NONYL OXADIAZOLYL DERIVATIVES AND THEIR MEDICAL USE<br/>[FR] NOUVEAUX DÉRIVÉS DE 1,4-DIAZA-BICYCLO[3.2.2]NONYL OXADIAZOLYLE ET LEUR UTILISATION MÉDICALE
  申请人：NEUROSEARCH AS

  公开号：WO2007138038A1

  公开（公告）日：2007-12-06

  [EN] This invention relates to novel 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyl derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances. Ar represents a phenyl group, which phenyl is substituted with methylenedioxy or ethylenedioxy.
  [FR] Nouveaux dérivés de 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyle et leur utilisation dans la fabrication de compositions pharmaceutiques. Il est apparu que les composés de l'invention étaient des ligands cholinergiques au niveau des récepteurs de l'acétylcholine nicotinique et des modulateurs des récepteurs et des transporteurs de la monoamine. Compte tenu de leur profil pharmacologique, ces composés peuvent convenir pour le traitement de maladies et de troubles aussi divers que celles et ceux en rapport avec le système cholinergique du système nerveux central, du système nerveux périphérique, de maladies ou de troubles associés à la contraction des muscles lisses, de maladies et de troubles d'origine endocrinienne, de maladies et de troubles associés à la neuro-dégénérescence, de maladies et de troubles en rapport avec l'inflammation, la douleur et les symptômes de sevrage dus à l'arrêt de l'abus de substances chimiques. Ar représente un groupe phényle, lequel phényle est substitué par un méthylènedioxy ou un éthylènedioxy.