(2S,3R,4R,5S,6R)-2-(2-(allyloxymethyl)-4-chloro-5-((5-(furan-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol | 1313513-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-2-(2-(allyloxymethyl)-4-chloro-5-((5-(furan-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2S,3R,4R,5S,6R)-2-[4-chloro-5-[[5-(furan-3-yl)-1,3-thiazol-2-yl]methyl]-2-(prop-2-enoxymethyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1313513-54-0
• 化学式: C₂₄H₂₆ClNO₇S
• 分子量: 507.992
• InChiKey: RWGWXKKFPBIKSP-MWFZDGHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-氨基-4-甲基苯甲酸 在 劳森试剂 、 N-甲基吗啉 、 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 氯化亚砜 、 lithium hydroxide monohydrate 、 偶氮二异丁腈 、 dimethyl sulfide borane 、 四丁基氟化铵 、 三氯化硼 、 三溴化磷 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 82.42h， 生成 (2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(furan-3-yl)thiazol-2-yl)methyl)-2-(hydroxymethyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol 、 (2S,3R,4R,5S,6R)-2-(2-(allyloxymethyl)-4-chloro-5-((5-(furan-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Thiazolylmethyl ortho-substituted phenyl glucoside library as novel C-aryl glucoside SGLT2 inhibitors

  摘要：

  In order to investigate SAR regarding proximal phenyl ring in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on proximal phenyl ring was conducted. During a series of lead optimization efforts, ortho-allyloxyphenyl 10p or ortho-hydroxyphenyl ha showed subnanomolar inhibitory activity against hSGLT2. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.052

文献信息

• Thiazole Derivatives as SGLT2 Inhibitors and Pharmaceutical Composition Comprising Same
  申请人：Lee Jinhwa

  公开号：US20130090298A1

  公开（公告）日：2013-04-11

  The present invention relates to a novel compound with thiazole ring having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney, and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly diabetes.

  本发明涉及一种新型含有噻唑环的化合物，具有对存在于肠和肾中的钠依赖性葡萄糖共转运体2（SGLT2）的抑制活性，以及包含该化合物作为活性成分的制药组合物，用于预防或治疗代谢性疾病，特别是糖尿病。
• US8586550B2
  申请人：——

  公开号：US8586550B2

  公开（公告）日：2013-11-19
• [EN] THIAZOLE DERIVATIVES AS SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME<br/>[FR] DÉRIVÉS DE THIAZOLE EN TANT QU'INHIBITEURS DE SGLT2 ET COMPOSITION PHARMACEUTIQUE COMPRENANT CEUX-CI
  申请人：GREEN CROSS CORP

  公开号：WO2011159067A2

  公开（公告）日：2011-12-22

  The present invention relates to a novel compound with thiazole ring having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney, and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly diabetes.
• Thiazolylmethyl ortho-substituted phenyl glucoside library as novel C-aryl glucoside SGLT2 inhibitors
  作者：Suk Ho Lee、Min Ju Kim、Sung-Han Lee、Jeongmin Kim、Hyun-Ju Park、Jinhwa Lee

  DOI：10.1016/j.ejmech.2011.03.052

  日期：2011.7

  In order to investigate SAR regarding proximal phenyl ring in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on proximal phenyl ring was conducted. During a series of lead optimization efforts, ortho-allyloxyphenyl 10p or ortho-hydroxyphenyl ha showed subnanomolar inhibitory activity against hSGLT2. (C) 2011 Elsevier Masson SAS. All rights reserved.