5-phenyl-1,2,4-thiadiazole | 74466-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-phenyl-1,2,4-thiadiazole
• CAS: 74466-89-0
• 化学式: C₈H₆N₂S
• mdl: MFCD18449794
• 分子量: 162.215
• InChiKey: LQIITQSGYNMPGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 5-phenyl-1,2,4-thiadiazole 在 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 butyl N-cyanobenzenecarboximidothioate
  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：

  N-[(E)-(二甲基氨基)亚甲基]硫代苯甲酰胺 在 吡啶 作用下， 以 乙醇 为溶剂， 生成 5-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

• (Phenylalkylaminoalkyloxy) -heteroaryl-compounds, processes and
  申请人：Kali-Chemie Pharma GmbH

  公开号：US05679699A1

  公开（公告）日：1997-10-21

  3-(Phenylalkylaminoalkyloxy)-heteroaryl compounds having heart rate lowering and/or anti-ischemic effects, methods for their preparation and pharmaceutical compositions containing them are described. The compounds correspond to the general formula I ##STR1## or to the general formula XXXI ##STR2## in which the substituents have the meanings given in the specification.

  本文描述了具有降低心率和/或抗缺血作用的3-（苯基烷基氨基烷氧基）-杂环化合物，以及它们的制备方法和包含它们的药物组合物。这些化合物对应于一般式I ##STR1## 或一般式XXXI ##STR2## 其中取代基的含义如规范中所述。
• (Phenylalkylaminoalkyloxy)-heteroaryl-compounds, processes and
  申请人：Kali-Chemie Pharma GmbH

  公开号：US05547967A1

  公开（公告）日：1996-08-20

  3-(Phenylalkylaminoalkylozy)-heteroaryl compounds having heart rate lowering and/or anti-ischemic effects, methods for their preparation and pharmaceutical compositions containing them are described. The compounds correspond to the general formula I ##STR1## or to the general formula XXXI ##STR2## in which the substituents have the meanings given the specification.

  本发明涉及一种具有降低心率和/或抗缺血效果的3-(苯基烷基氨基烷氧基)-杂环化合物，以及制备它们的方法和包含它们的药物组合物。所述化合物对应于一般式I ##STR1## 或一般式XXXI ##STR2## 其中取代基的含义在说明中给出。
• New synthesis of 1,2,4-thiadiazoles
  作者：Yang-i Lin、S. A. Lang、Sharon R. Petty

  DOI：10.1021/jo01307a006

  日期：1980.9
• Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives
  作者：Ana Castro、Arantxa Encinas、Carmen Gil、Stefan Bräse、Williams Porcal、Concepción Pérez、Francisco J. Moreno、Ana Martínez

  DOI：10.1016/j.bmc.2007.09.016

  日期：2008.1

  The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3 beta inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3 beta activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated. (c) 2007 Elsevier Ltd. All rights reserved.
• Photochemistry of Phenyl-Substituted 1,2,4-Thiadiazoles. ¹⁵N-Labeling Studies
  作者：James W. Pavlik、Chuchawin Changtong、Vikki M. Tsefrikas

  DOI：10.1021/jo0340915

  日期：2003.6.1

  Irradiation of 5-phenyl-1,2,4-thiadiazole (6) resulted in the formation of benzonitrile (5), 3-phenyl-1,2,4-thiadiazole (4), phenyl- and diphenyl-1,3,5-triazines (7 and 8), and a trace quantity of diphenyl-1,2,4-thiadiazole (9). The formation of 4 5, 7, and 8 can be explained in terms of photoinduced electrocyclic ring closure resulting in the formation of an intermediate 4-phenyl-1,3-diaza-5thiabicyclo[2.1.0]pentene. N-15-labeling experiments revealed that sulfur can undergo sigmatropic shifts around all four sides of the diazetine ring. Thus, irradiation of 6-4-N-15 led to the formation of 6-2-N-15 and an equimolar mixture of 4-2-N-15 and 4-4-N-15. The thiabicyclo[2.1.0]pentene intermediate is also suggested to undergo sulfur elimination resulting in the formation of phenyldiazacyclobutadiene, which can undergo complete fragmentation to benzonitrile or [4+2] cycloaddition leading to unstable tricyclic adducts, the suggested precursors of the 1,3,5-triazine products 7 and 8. The observed N-15 distribution in 7 and 8 is consistent with this mechanism. Irradiation of 4 led only to the formation of 5. N-15-labeling experiments show that 4 does not undergo electrocyclic ring closure but reacts exclusively by photofragmentation of the thiadiazole ring.