5-formyl-3-phenyl-1,2,4-thiadiazole | 505081-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-formyl-3-phenyl-1,2,4-thiadiazole
• 英文别名: 3-Phenyl-1,2,4-thiadiazole-5-carbaldehyde
• CAS: 505081-79-8
• 化学式: C₉H₆N₂OS
• 分子量: 190.225
• InChiKey: NAVFJQHESZICJE-UHFFFAOYSA-N

物化性质

• 沸点：
  357.2±25.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-formyl-3-phenyl-1,2,4-thiadiazole 、 N-叔丁基羟胺盐酸盐 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以82%的产率得到α(Z)-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-tert-butylnitrone
  参考文献：
  名称：

  Heteroarylnitrones as Drugs for Neurodegenerative Diseases: Synthesis, Neuroprotective Properties, and Free Radical Scavenger Properties

  摘要：

  New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, alpha-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.

  DOI：

  10.1021/jm8006432
• 作为产物：
  描述：

  5-(hydroxymethyl)-3-phenyl-1,2,4-thiadiazole 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以0.13 g的产率得到5-formyl-3-phenyl-1,2,4-thiadiazole
  参考文献：
  名称：

  Heteroarylnitrones as Drugs for Neurodegenerative Diseases: Synthesis, Neuroprotective Properties, and Free Radical Scavenger Properties

  摘要：

  New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, alpha-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.

  DOI：

  10.1021/jm8006432

文献信息

• POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
  申请人：Glinka Tomasz

  公开号：US20100152098A1

  公开（公告）日：2010-06-17

  Disclosed are compounds having polybasic functionalities. The compounds inhibit bacterial efflux pump inhibitors and are used in combination with an anti-bacterial agent to treat or prevent bacterial infections. These combinations can be effective against bacterial infections that have developed resistance to anti-bacterial agents through an efflux pump mechanism.

  本发明涉及具有多元功能的化合物。这些化合物可以抑制细菌外排泵抑制剂，并与抗菌剂结合使用，以治疗或预防细菌感染。这些组合物可以有效地对抗通过外排泵机制对抗菌剂产生抗性的细菌感染。
• US8178490B2
  申请人：——

  公开号：US8178490B2

  公开（公告）日：2012-05-15
• [EN] POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTIC USES THEREOF<br/>[FR] INHIBITEURS POLYBASIQUES DE POMPE À EFFLUX BACTÉRIENNE ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：MPEX PHARMACEUTICALS INC

  公开号：WO2010054102A2

  公开（公告）日：2010-05-14

  Disclosed are compounds having polybasic functionalities. The compounds inhibit bacterial efflux pump inhibitors and are used in combination with an anti-bacterial agent to treat or prevent bacterial infections. These combinations can be effective against bacterial infections that have developed resistance to anti-bacterial agents through an efflux pump mechanism.
• Heteroarylnitrones as Drugs for Neurodegenerative Diseases: Synthesis, Neuroprotective Properties, and Free Radical Scavenger Properties
  作者：Williams Porcal、Paola Hernández、Mercedes González、Ana Ferreira、Claudio Olea-Azar、Hugo Cerecetto、Ana Castro

  DOI：10.1021/jm8006432

  日期：2008.10.9

  New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, alpha-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.