(2R,3R,4S,5S,6R)-2-(5-benzylthiazol-2-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol | 1242654-20-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6R)-2-(5-benzylthiazol-2-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2R,3R,4S,5S,6R)-2-(5-Benzylthiazol-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2R,3R,4S,5S,6R)-2-(5-benzyl-1,3-thiazol-2-yl)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1242654-20-1
• 化学式: C₁₆H₁₉NO₅S
• 分子量: 337.397
• InChiKey: BSYYGZFJQIYYIE-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  phenyl(2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)thiazol-5-yl)methanol 在 碘代三甲硅烷 、 甲醇 作用下， 生成 (2R,3R,4S,5S,6R)-2-(5-benzylthiazol-2-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors

  摘要：

  With anticipation of the improvement in biological aspects in our SGLT2 program, novel pyridazinyl and thiazolyl analogs were designed and efficiently synthesized. The installation of the pyridazine ring at the anomeric carbon of D-glucopyranose was carried out in a stereoselective fashion. On the other hand, a series of thiazolyl analogs was also synthesized through a coupling reaction between perbenzyl gluconolactone 9 and 2-lithiothiazole. Biological activities of the compounds thus prepared were evaluated by the in vitro SGLT2 inhibition assay. Considering assay results, the novel benzylpyridazinyl and benzyl-thiazolyl analogs, disclosed in this article, could be a quick reference to prospective SGLT2 inhibitors useful for pharmacotherapy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.076

文献信息

• Synthesis of pyridazine and thiazole analogs as SGLT2 inhibitors
  作者：Suk Youn Kang、Kwang-Seop Song、Junwon Lee、Sung-Han Lee、Jinhwa Lee

  DOI：10.1016/j.bmc.2010.06.076

  日期：2010.8

  With anticipation of the improvement in biological aspects in our SGLT2 program, novel pyridazinyl and thiazolyl analogs were designed and efficiently synthesized. The installation of the pyridazine ring at the anomeric carbon of D-glucopyranose was carried out in a stereoselective fashion. On the other hand, a series of thiazolyl analogs was also synthesized through a coupling reaction between perbenzyl gluconolactone 9 and 2-lithiothiazole. Biological activities of the compounds thus prepared were evaluated by the in vitro SGLT2 inhibition assay. Considering assay results, the novel benzylpyridazinyl and benzyl-thiazolyl analogs, disclosed in this article, could be a quick reference to prospective SGLT2 inhibitors useful for pharmacotherapy. (C) 2010 Elsevier Ltd. All rights reserved.