2-(2-ethyl-4-methyl-thiazol-5-yl)-ethanol | 760210-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-ethyl-4-methyl-thiazol-5-yl)-ethanol
• 英文别名: 2-(2-Aethyl-4-methyl-thiazol-5-yl)-aethanol；2-(2-ethyl-4-methyl-1,3-thiazol-5-yl)ethanol
• CAS: 760210-65-9
• 化学式: C₈H₁₃NOS
• 分子量: 171.263
• InChiKey: LEJKIGXZLKOOAU-UHFFFAOYSA-N

物化性质

• 沸点：
  282.5±25.0 °C(predicted)
• 密度：
  1.130±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-ethyl-4-methyl-thiazol-5-yl)-ethanol 、 3-(chloromethyl)-6-methylpyridin-2-ylamine hydrochloride 反应 0.25h， 生成 3-(2-amino-6-methyl-pyridin-3-ylmethyl)-2-ethyl-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium chloride hydrochloride
  参考文献：
  名称：

  Synthesis, in vitro and in vivo activity of thiamine antagonist transketolase inhibitors

  摘要：

  Tumor cells extensively utilize the pentose phosphate pathway for the synthesis of ribose. Transketolase is a key enzyme in this pathway and has been suggested as a target for inhibition in the treatment of cancer. In a pharmacodynamic study, nude mice with xenografted HCT-116 tumors were dosed with 1 ('N3'-pyridyl thiamine'; 3-(6-methyl-2-amino-pyridin-3-ylmethyl)-5-(2-hydroxyethyl)-4-methyl-thiazol-3-ium chloride hydrochloride), an analog of thiamine, the co-factor of transketolase. Transketolase activity was almost completely suppressed in blood, spleen, and tumor cells, but there was little effect on the activity of the other thiamine-utilizing enzymes alpha-ketoglutarate dehydrogenase or glucose-6-phosphate dehydrogenase. Synthesis and SAR of transketolase inhibitors is described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.101
• 作为产物：
  描述：

  acetic acid 2-(2-ethyl-4-methyl-thiazol-5-yl)-ethyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以70%的产率得到2-(2-ethyl-4-methyl-thiazol-5-yl)-ethanol
  参考文献：
  名称：

  Synthesis, in vitro and in vivo activity of thiamine antagonist transketolase inhibitors

  摘要：

  Tumor cells extensively utilize the pentose phosphate pathway for the synthesis of ribose. Transketolase is a key enzyme in this pathway and has been suggested as a target for inhibition in the treatment of cancer. In a pharmacodynamic study, nude mice with xenografted HCT-116 tumors were dosed with 1 ('N3'-pyridyl thiamine'; 3-(6-methyl-2-amino-pyridin-3-ylmethyl)-5-(2-hydroxyethyl)-4-methyl-thiazol-3-ium chloride hydrochloride), an analog of thiamine, the co-factor of transketolase. Transketolase activity was almost completely suppressed in blood, spleen, and tumor cells, but there was little effect on the activity of the other thiamine-utilizing enzymes alpha-ketoglutarate dehydrogenase or glucose-6-phosphate dehydrogenase. Synthesis and SAR of transketolase inhibitors is described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.101

文献信息

• Thiazole-based nitric oxide donors having aryl substituent(s) and uses thereof
  申请人：Assaf Peter

  公开号：US20060183718A1

  公开（公告）日：2006-08-17

  Disclosed are novel NO-donating compounds, designed such that when NO is released from the compound a residue which is a naturally occurring metabolite is formed, and thus a development of tolerance to the compounds upon repetitive administration is prevented or decreased. Also disclosed are methods of preparing such NO-donating compounds, pharmaceutical compositions and medical devices containing such compounds and methods utilizing such compounds in the treatment of various medical conditions.

  本发明涉及一种新型的NO供体化合物，其设计使得当NO从该化合物中释放时，会形成一种天然代谢产物的残留物，从而防止或减少反复使用该化合物时产生耐药性。同时还揭示了制备这种NO供体化合物的方法，包括含有该化合物的制药组合物和医疗器械，以及利用这种化合物治疗各种医疗状况的方法。
• Thiazole-based nitric oxide donors having acyl substuent(s) and uses thereof
  申请人：Assaf Peter

  公开号：US20060183913A1

  公开（公告）日：2006-08-17

  Disclosed are novel NO-donating compounds, designed such that when NO is released from the compound a residue which is a naturally occurring metabolite is formed, and thus a development of tolerance to the compounds upon repetitive administration is prevented or decreased. Also disclosed are methods of preparing such NO-donating compounds, pharmaceutical compositions and medical devices containing such compounds and methods utilizing such compounds in the treatment of various medical conditions.

  本发明涉及新型NO供体化合物，其设计是当NO从化合物释放时，形成一种天然代谢产物的残留物，从而防止或减少反复给药时对化合物的耐受性发展。本发明还涉及制备这种NO供体化合物的方法，含有这种化合物的药物组合物和医疗器械，以及利用这种化合物治疗各种医疗状况的方法。
• Thiazole-based nitric oxide donors having at least two thiazole moieties and uses thereof
  申请人：Assaf Peter

  公开号：US20060183912A1

  公开（公告）日：2006-08-17

  Disclosed are novel NO-donating compounds, designed such that when NO is released from the compound a residue which is a naturally occurring metabolite is formed, and thus a development of tolerance to the compounds upon repetitive administration is prevented or decreased. Also disclosed are methods of preparing such NO-donating compounds, pharmaceutical compositions and medical devices containing such compounds and methods utilizing such compounds in the treatment of various medical conditions.

  本发明涉及一种新型的NO供体化合物，其设计使得当NO从化合物中释放出来时，形成一个天然代谢物残留物，从而预防或减少反复使用这些化合物时的耐受性发展。同时还揭示了制备这种NO供体化合物的方法，包括含有这种化合物的药物组合物和医疗器械以及利用这种化合物治疗各种医疗状况的方法。
• Thiazole-based nitric oxide donors capable of releasing two or more nitric oxide molecules and uses thereof
  申请人：Assaf Peter

  公开号：US20060069139A1

  公开（公告）日：2006-03-30

  Disclosed are novel NO-donating compounds, designed such that when NO is released from the compound a residue which is a naturally occurring metabolite is formed, and thus a development of tolerance to the compounds upon repetitive administration is prevented or decreased. Also disclosed are methods of preparing such NO-donating compounds, pharmaceutical compositions and medical devices containing such compounds and methods utilizing such compounds in the treatment of various medical conditions.

  本发明涉及新型NO供体化合物，其设计是当NO从化合物释放时，形成一种天然代谢产物残留物，从而防止或减少重复给药时对化合物的耐受性的发展。本发明还涉及制备这种NO供体化合物的方法、包含这种化合物的药物组合物和医疗器械，以及利用这种化合物治疗各种医疗状况的方法。
• Thiazole-based nitric oxide donors having alkyl substuent(s) and uses thereof
  申请人：Assaf Peter

  公开号：US20060069138A1

  公开（公告）日：2006-03-30

  Disclosed are novel NO-donating compounds, designed such that when NO is released from the compound a residue which is a naturally occurring metabolite is formed, and thus a development of tolerance to the compounds upon repetitive administration is prevented or decreased. Also disclosed are methods of preparing such NO-donating compounds, pharmaceutical compositions and medical devices containing such compounds and methods utilizing such compounds in the treatment of various medical conditions.

  本发明涉及新型NO供体化合物，其设计是当NO从化合物释放时，形成一个天然存在的代谢产物残留物，从而防止或减少在重复给药时对化合物的耐受性的发展。同时还揭示了制备这种NO供体化合物的方法，含有这种化合物的制药组合物和医疗器械以及利用这种化合物治疗各种医疗状况的方法。