[A] 5-mercaptothiazole | 120405-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [A] 5-mercaptothiazole
• 英文别名: 5-Thiazolethiol；1,3-thiazole-5-thiol
• CAS: 120405-09-6
• 化学式: C₃H₃NS₂
• 分子量: 117.196
• InChiKey: PKXGJLZKCTVTDR-UHFFFAOYSA-N

物化性质

• 沸点：
  208.1±13.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-nitro-6-bromo-1-indanone ethylene ketal 、 [A] 5-mercaptothiazole 在 吡啶 、 氢氧化钾 作用下， 反应 2.0h， 生成 5-(6-Nitrospiro[1,2-dihydroindene-3,2'-1,3-dioxolane]-5-yl)sulfanyl-1,3-thiazole
  参考文献：
  名称：

  Cyclooxygenase-2 Inhibitors. Synthesis and Pharmacological Activities of 5-Methanesulfonamido-1-indanone Derivatives

  摘要：

  The recent discovery of an alternative form cyclooxygenase (cyclooxygenase-2, COX-2), which has been proposed to play a significant role in inflammatory conditions, may provide an opportunity to develop anti-inflammatory drugs with fewer side effects than existing nonsteroidal anti-inflammatory drugs (NSAIDs). We have now identified 6-[(2,4-difluorophenyl)thio]-5-methanesulfonamido-1-indanone (20) (L-745,337) as a potent, selective, and orally active COX-2 inhibitor. The structure-activity relationships in this series have been extensively studied. Ortho- and para-substituted B-phenyl substitutents are optimal for in vitro potency. Replacement of this phenyl ring by a variety of heterocycles gave compounds that were less active. The methanesulfonamido group seems to be the optimal group at the 5-position of the indanone system. Compound 20 has an efficacy profile that is superior or comparable to that of the nonselective COX inhibitor indomethacin in animal models of inflammation, pain, and fever and appears to be nonulcerogenic within the dosage ranges required for functional efficacy. Although 20 and its oxygen linkage analog 2 (flosulide) are equipotent in the in vitro assays, compound 20 is more potent in the rat paw edema assay, has a longer t(1/2) in squirrel monkeys, and seems less ulcergenic than 2 in rats.

  DOI：

  10.1021/jm00025a007

文献信息

• Highly potent, non-basic 5-HT6 ligands. Site mutagenesis evidence for a second binding mode at 5-HT6 for antagonism
  作者：Ralph N. Harris、Russel S. Stabler、David B. Repke、James M. Kress、Keith A. Walker、Renee S. Martin、Julie M. Brothers、Mariola Ilnicka、Simon W. Lee、Tara Mirzadegan

  DOI：10.1016/j.bmcl.2010.03.110

  日期：2010.6

  A series of 5-HT6 ligands derived from (R)-1-(amino) methyl-6-(phenyl) sulfonyltetralin was prepared that yielded several non-basic analogs having sub-nanomolar affinity. Ligand structure-activity relationships, receptor point mutation studies, and molecular modeling of these novel ligands all combined to reveal a new alternative binding mode to 5-HT6 for antagonism. (C) 2010 Published by Elsevier Ltd.