5-苯并[1,3]二氧代-5-基-[1,3,4]噁二唑-2-硫醇 | 63698-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 5-苯并[1,3]二氧代-5-基-[1,3,4]噁二唑-2-硫醇
• 英文名称: 2-mercapto-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole
• 英文别名: 5-(benzo[d][1,3]dioxol-5-yl)-1,3,4-oxadiazole-2-thiol；5-(3,4-methylene-dioxyphenyl)-1,3,4-oxadiazol-2-thiol；5-benzo[1,3]dioxol-5-yl-3H-[1,3,4]oxadiazole-2-thione；5-benzo[1,3]dioxol-5-yl-[1,3,4]oxadiazole-2-thiol；5-(1,3-benzodioxol-5-yl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 63698-52-2
• 化学式: C₉H₆N₂O₃S
• mdl: MFCD03988520
• 分子量: 222.224
• InChiKey: JPZJNDJPRJSGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-苯并[1,3]二氧代-5-基-[1,3,4]噁二唑-2-硫醇 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 2-phenoxymethyl-5-(3,4-methylenedioxyphenyl)-s-triazolo<3,4-b>-1,3,4-thiadiazole
  参考文献：
  名称：

  Prasad, A. R.; Ramalingam, T.; Rao, A. Bhaskar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 566 - 568

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒酸 在 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 5-苯并[1,3]二氧代-5-基-[1,3,4]噁二唑-2-硫醇
  参考文献：
  名称：

  Synthesis, Characterization and Urease Inhibiting Derivatives of 5-(3,4-Methylenedioxyphenyl)-1,3,4-Oxadiazol-2-thiol

  摘要：

  在本研究中，评估了含有1,3,4-噁二唑基团的化合物的尿素酶抑制活性，发现它们具有潜在的抑制作用。通过一系列步骤，使用3,4-亚甲二氧基苯甲酸（1）合成了5-(3,4-亚甲二氧基苯基)-1,3,4-噁二唑-2-硫醇（4）。进一步通过与烷基/芳烷基卤化物（5a-h）在DMF中使用LiH作为活化剂反应，生成了S-取代的5-(3,4-亚甲二氧基苯基)-1,3,4-噁二唑衍生物（6a-h）。所有合成的化合物均通过IR、1H NMR和EIMS光谱分析得到良好支持。对尿素酶的酶抑制活性显示这些分子是该酶的强效抑制剂。

  DOI：

  10.14233/ajchem.2014.16132

文献信息

• [EN] NOVEL 1,4-DIAZA-BICYCLO[3.2.1]OCTANE DERIVATIVES USEFUL AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS DE 1,4-DIAZABICYCLO[3.2.1]OCTANE UTILES COMME MODULATEURS DU RÉCEPTEUR NICOTINIQUE À L'ACÉTYLCHOLINE
  申请人：NEUROSEARCH AS

  公开号：WO2010130768A1

  公开（公告）日：2010-11-18

  This invention relates to novel 1,4-diaza-bicyclo[3.2.1]octane 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 and modulators of the monoamine receptors and transporters. 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.

  这项发明涉及新颖的1,4-二氮杂双环[3.2.1]辛烷衍生物及其在制备药物组合物中的应用。该发明的化合物被发现是胆碱能受体的胆碱能配体，并且是单胺受体和转运体的调节剂。由于它们的药理特性，该发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩、内分泌疾病或紊乱、神经退行性疾病、炎症、疼痛以及由于滥用化学物质终止而引起的戒断症状等多种疾病或紊乱有用。
• [EN] NOVEL 1,4-DIAZA-BICYCLO[3.2.2]NONYL OXADIAZOLYL DERIVATIVES USEFUL AS MODULATOR OF NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] NOUVEAUX DÉRIVÉS DE 1,4-DIAZA-BICYCLO[3.2.2]NONYLOXADIAZOLYLE UTILES EN TANT QUE MODULATEURS DE RÉCEPTEURS D'ACÉTYLCHOLINE NICOTINIQUES
  申请人：NEUROSEARCH AS

  公开号：WO2009112460A1

  公开（公告）日：2009-09-17

  This invention relates to novel N-oxides of a 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyl derivative 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.

  这项发明涉及一种新颖的1,4-二氮杂双环[3.2.2]壬基噁二唑衍生物的N-氧化物及其在制备药物组合物中的应用。该发明的化合物被发现是胆碱能受体的胆碱能配体。由于它们的药理特性，该发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩、内分泌疾病或紊乱、神经退行性疾病、炎症、疼痛以及由于滥用化学物质终止而引起的戒断症状等多种疾病或紊乱有用。
• Anticonvulsant and Antiproteolytic Properties of 3,5-Disubstituted Oxadiazole-2-thiones and Their Inhibition of Respiration in Rat Brain Homogenates
  作者：Sunil K. Chaudhary、Mahima Chaudhary、Anshumali Chaudhari、Surendra S. Parmar

  DOI：10.1002/jps.2600671104

  日期：1978.11

  succinate by rat brain homogenates. Antiproteolytic activity of these substituted oxadiazole-2-thiones was reflected by their ability to inhibit trypsin hydrolysis of bovine serum albumin. These results indicated that the inhibition of cellular respiration and antiproteolytic activity of these substituted oxadiazole-2-thiones is not the biochemical basis for their anticonvulsant activity.

  合成了八种5-（3,4-亚甲基二氧基苯基）-3-芳基氨基甲基-I，3,4-恶二唑-2-硫酮，以其敏锐的熔点，元素分析和IR光谱为特征，并评估了其抗惊厥活性。所有取代的恶二唑-2-硫酮都具有抗惊厥活性，这是由于它们能够以100 mg / kg ip的剂量提供对戊烯四唑诱发的小鼠惊厥的10-70％的保护能力。这些化合物抑制大鼠脑匀浆的体外烟酰胺腺嘌呤二核苷酸（NAD）依赖的丙酮酸，α-酮戊二酸酯和NADH的氧化，以及大鼠脑匀浆的琥珀酸的NAD独立的氧化。这些取代的恶二唑-2-硫酮的抗蛋白水解活性反映在它们抑制胰蛋白酶水解牛血清白蛋白的能力上。
• 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。
• NOVEL 1,4-DIAZA-BICYCLO[3.2.1]OCTANE DERIVATIVES USEFUL AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
  申请人：Peters Dan

  公开号：US20120071469A1

  公开（公告）日：2012-03-22

  This invention relates to novel 1,4-diaza-bicyclo[3.2.1]octane 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 and modulators of the monoamine receptors and transporters. 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[3.2.1]辛烷衍生物及其在制造药物组合物方面的用途。本发明化合物被发现是乙酰胆碱受体的胆碱能配体和单胺受体和转运体的调节剂。由于其药理特性，本发明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，与平滑肌收缩有关的疾病或疾病，内分泌疾病或疾病，与神经退行性有关的疾病或疾病，与炎症、疼痛和化学物质滥用终止引起的戒断症状有关的疾病或疾病具有用处。