3-hydroxy-4-methyl-1,2,5-thiadiazole | 5728-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-hydroxy-4-methyl-1,2,5-thiadiazole
• 英文别名: 4-methyl-[1,2,5]thiadiazol-3-ol；3-methyl-4-hydroxy-1,2,5-thiadiazole；3-Hydroxy-4-methyl-1,2,5-thiadiazol；3-Methyl-4-hydroxy-1,2,5-thiadiazol；4-Methyl-1,2,5-thiadiazol-3-ol；4-methyl-1,2,5-thiadiazol-3-one
• CAS: 5728-08-5
• 化学式: C₃H₄N₂OS
• 分子量: 116.144
• InChiKey: LAHGPTMNWMCUNX-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153 °C
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methyl-1,2,5-thiadiazole 、 3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl 在 CsF/silica 作用下， 以 乙腈 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Drug Resistance Reversal In Neoplastic Disease

  摘要：

  本发明涉及用于阻止或逆转肿瘤性疾病化疗耐药效应的化合物、组合物和方法。具体描述了羟胺的使用。

  公开号：

  US20080200405A1
• 作为产物：
  描述：

  2-氨基丙酰胺 在 二氯化二硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-hydroxy-4-methyl-1,2,5-thiadiazole
  参考文献：
  名称：

  General synthetic system for 1,2,5-thiadiazoles

  摘要：

  DOI：

  10.1021/jo01284a040

文献信息

• Thiadiazole Derivatives: Highly Potent and Specific HIV-1 Reverse Transcriptase Inhibitors
  作者：Yasuaki Hanasaki、Hiroyuki Watanabe、Kimio Katsuura、Hiromitsu Takayama、Seiichiro Shirakawa、Kentaro Yamaguchi、Shin-ichiro Sakai、Katsushi Ijichi、Masatoshi Fujiwara

  DOI：10.1021/jm00012a002

  日期：1995.6
• WO2008/103613
  申请人：——

  公开号：——

  公开（公告）日：——
• 2-Amino-3-(3-hydroxy-1,2,5-thiadiazol-4-yl)propionic acid: resolution, absolute stereochemistry and enantiopharmacology at glutamate receptors
  作者：Tommy N. Johansen、Yves L. Janin、Birgitte Nielsen、Karla Frydenvang、Hans Bräuner-Osborne、Tine B. Stensbøl、Stine B. Vogensen、Ulf Madsen、Povl Krogsgaard-Larsen

  DOI：10.1016/s0968-0896(02)00041-x

  日期：2002.7

  In order to identify new subtype-selective (S)-glutamate (Glu) receptor ligands we have synthesized (RS)-2-amino-3-(3-hydroxy-1,2,5-thiadiazol-4-yl)propionic acid [(RS)-TDPA]. Resolution of (RS)-TDPA by chiral chromatography was performed using a Crownpac CR(+) column affording (R)- and (S)-TDPA of high enantiomeric purity (enantiomeric excess=99.9%). An X-ray crystallographic analysis revealed that the early eluting enantiomer has R-configuration. Both enantiomers showed high affinity as well as high agonist activity at (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptors, determined using a [H-3]AMPA binding assay and an electrophysiological model, respectively. The affinities and agonist activities obtained for (R)-TDPA (IC50=0.265 muM and EC50-6.6 muM, respectively) and (S)-TDPA (IC50=0.0065 muM and EC50=20 muM. respectively) revealed a remarkably low AMPA receptor stereoselectivity. (S)-TDPA showing the highest affinity and (R)-TDPA the most potent agonist activity. In addition, (S)-TDPA was shown to interact with synaptosomal Glu uptake sites displacing [H-3](R)-aspartic acid (IC(50)approximate to390 muM). An enantiospecific and subtype-selective agonist activity was observed for (S)-TDPA at group I metabotropic Glu (mGlu) receptors (EC50-13 muM at mGlu(5) and EC50=95 muM at mGlu(1)). (C) 2002 Elsevier Science Ltd. All rights reserved.