5-(1H-吡咯-2-基)-1,3,4-恶二唑-2-硫醇 | 10551-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 5-(1H-吡咯-2-基)-1,3,4-恶二唑-2-硫醇
• 英文名称: 5-(1H-pyrrol-2-yl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5--1,3,4-oxadiazol-2-thiol；5-pyrrol-2-yl-3H-[1,3,4]oxadiazole-2-thione；5-mercapto-2-(pyrrol-2-yl)-1,3,4-oxadiazole；5-(1H-pyrrol-2-yl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 10551-16-3
• 化学式: C₆H₅N₃OS
• 分子量: 167.191
• InChiKey: LPUDVYUQYFEDPY-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208 °C (decomp)
• 沸点：
  296.7±32.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2,6-二氯氯苄 、 5-(1H-吡咯-2-基)-1,3,4-恶二唑-2-硫醇 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到2-((2,6-dichlorobenzyl)thio)-5-(1H-pyrrol-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Yoda1 analogue (Dooku1) which antagonizes Yoda1-evoked activation of Piezo1 and aortic relaxation

  摘要：

  Background and PurposeThe mechanosensitive Piezo1 channel has important roles in vascular physiology and disease. Yoda1 is a small‐molecule agonist, but the pharmacology of these channels is otherwise limited.Experimental ApproachYoda1 analogues were generated by synthetic chemistry. Intracellular Ca2+ and Tl+ measurements were made in HEK 293 or CHO cell lines overexpressing channel subunits and in HUVECs, which natively express Piezo1. Isometric tension recordings were made from rings of mouse thoracic aorta.Key ResultsModification of the pyrazine ring of Yoda1 yielded an analogue, which lacked agonist activity but reversibly antagonized Yoda1. The analogue is referred to as Dooku1. Dooku1 inhibited 2 μM Yoda1‐induced Ca2+‐entry with IC50s of 1.3 μM (HEK 293 cells) and 1.5 μM (HUVECs) yet failed to inhibit constitutive Piezo1 channel activity. It had no effect on endogenous ATP‐evoked Ca2+ elevation or store‐operated Ca2+ entry in HEK 293 cells or Ca2+ entry through TRPV4 or TRPC4 channels overexpressed in CHO and HEK 293 cells. Yoda1 caused dose‐dependent relaxation of aortic rings, which was mediated by an endothelium‐ and NO‐dependent mechanism and which was antagonized by Dooku1 and analogues of Dooku1.Conclusion and ImplicationsChemical antagonism of Yoda1‐evoked Piezo1 channel activity is possible, and the existence of a specific chemical interaction site is suggested with distinct binding and efficacy domains.

  DOI：

  10.1111/bph.14188
• 作为产物：
  描述：

  2-吡咯甲酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-(1H-吡咯-2-基)-1,3,4-恶二唑-2-硫醇
  参考文献：
  名称：

  10.1021/acs.jmedchem.4c00322

  摘要：

  DOI：

  10.1021/acs.jmedchem.4c00322

文献信息

• [EN] DIAZABICYCLONONYL OXADIAZOLE COMPOUNDS AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS<br/>[FR] COMPOSÉS DIAZABICYCLONONYLOXADIAZOLE ET LEUR UTILISATION EN TANT QUE MODULATEURS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：NEUROSEARCH AS

  公开号：WO2011073296A1

  公开（公告）日：2011-06-23

  This invention relates to diazabicyclononyl oxadiazolyl derivatives, which are found to-be modulators of 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. Ar1 represents a pyrrolyl group, optionally substituted with alkyl or halo-alkyl.

  这项发明涉及二氮杂双环壬酰胺基氧代二唑基衍生物，发现它们是尼古丁型乙酰胆碱受体的调节剂。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）的胆碱能系统、周围神经系统（PNS）、平滑肌收缩、内分泌疾病、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各种疾病或紊乱具有用处。Ar1代表一种吡咯基团，可选地取代为烷基或卤代烷基。
• [EN] LABELLED AND UN-LABELLED METHYL-PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL USE<br/>[FR] DÉRIVÉS MÉTHYL-PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE MARQUÉS ET NON MARQUÉS ET LEUR APPLICATION MÉDICALE
  申请人：NEUROSEARCH AS

  公开号：WO2012139925A1

  公开（公告）日：2012-10-18

  The present invention relates to certain labelled or un-labelled pyrrolyl-oxadizolyl-diazabicyclononane derivatives and their medical use. Furthermore, the present invention relates to the use of said derivatives in their labelled form in diagnostic methods, in particular for in vivo receptor imaging (neuroimaging).

  本发明涉及某些标记或未标记的吡咯基-噁唑基-二氮杂双环壬烷衍生物及其医学用途。此外，本发明还涉及使用所述衍生物的标记形式在诊断方法中的应用，特别是用于体内受体成像（神经成像）。
• LABELLED PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR USE IN DIAGNOSTIC METHODS
  申请人：Peters Dan

  公开号：US20120288443A1

  公开（公告）日：2012-11-15

  The present invention relates to certain labelled pyrrolyl-oxadizolyl-diazabicyclononane derivatives. Furthermore, the present invention relates to the use of said derivatives in their labelled form in diagnostic methods, in particular for in vivo receptor imaging (neuroimaging).

  本发明涉及某些标记的吡咯基-噁唑基-二氮杂双环壬烷衍生物。此外，本发明涉及所述衍生物在其标记形式下在诊断方法中的使用，特别是用于体内受体成像（神经成像）。
• LABELLED AND UN-LABELLED METHYL-PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL USE
  申请人：Peters Dan

  公开号：US20140030190A1

  公开（公告）日：2014-01-30

  The present invention relates to certain labelled or un-labelled pyrrolyl-oxadizolyl-diazabicyclononane derivatives and their medical use. Furthermore, the present invention relates to the use of said derivatives in their labelled form in diagnostic methods, in particular for in vivo receptor imaging (neuroimaging).

  本发明涉及某些带标记或未标记的吡咯基-噁唑基-二氮杂双环壬烷衍生物及其医药用途。此外，本发明涉及在其标记形式下使用所述衍生物的诊断方法，特别是用于体内受体成像（神经影像学）。
• DIAZABICYCLONONYL OXADIAZOLE COMPOUNDS AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS
  申请人：Peters Dan

  公开号：US20130004428A1

  公开（公告）日：2013-01-03

  This invention relates to diazabicyclononyl oxadiazolyl derivatives, which are found to-be modulators of 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 1 represents a pyrrolyl group, optionally substituted with alkyl or halo-alkyl.

  本发明涉及二氮杂双环壬基噁唑衍生物，其被发现是乙酰胆碱受体的调节剂。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）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩有关的疾病或紊乱、内分泌疾病或紊乱、神经退行性疾病或紊乱、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各种疾病或紊乱有用。其中Ar1代表一个吡咯基团，可选地被烷基或卤代烷基取代。