6-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one | 27182-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
• 英文别名: 6-chloro-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one；6-chloro-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one
• CAS: 27182-30-5
• 化学式: C₆H₄ClN₃O
• mdl: MFCD09994110
• 分子量: 169.57
• InChiKey: RAEMFDQJNPNIOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 、 6-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-((6-chloro-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties

  摘要：

  The sodium glucose co-transporter 2 (SGLT2) has received considerable attention in recent years as a target for the treatment of type 2 diabetes mellitus. This report describes the design, synthesis and structure-activity relationship (SAR) of C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties as novel SGLT2 inhibitors. Compounds 5p and 33b demonstrated high potency in inhibiting SGLT2 and high selectivity against SGLT1. The in vitro ADMET properties of these compounds will also be discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.036

文献信息

• SGLT-2 INHIBITORS, METHODS OF MAKING THEM, AND USES THEREOF
  申请人：LIU Shuang

  公开号：US20110237527A1

  公开（公告）日：2011-09-29

  The present invention relates to compounds which are inhibitors of sodium dependent glucose co-transporter-2 (SGLT-2). These compounds are used in the treatment of various disorders, including diabetes, impaired glucose tolerance, insulin resistance, retinopathy, nephropathy, neuropathy, cataracts, hyperglycemia, hyperinsulinemia, hyperchlolesterolemia, elevated blood level of free fatty acids or glycerol, hyperlipidemia, hypertriglyceridemia, obesity, wound healing, tissue ischemia, atherosclerosis, and hypertension. These compounds and compositions are also useful for treating and preventing kidney stones, hyperuricemia, gout, and hyponatremia. Methods of making these compounds are also described in the present invention.

  本发明涉及一类抑制钠依赖性葡萄糖共转运蛋白-2（SGLT-2）的化合物。这些化合物用于治疗各种疾病，包括糖尿病、糖耐量受损、胰岛素抵抗、视网膜病变、肾病、神经病变、白内障、高血糖、高胰岛素血症、高胆固醇血症、游离脂肪酸或甘油的血液水平升高、高脂血症、高甘油三酯血症、肥胖、伤口愈合、组织缺血、动脉粥样硬化和高血压。这些化合物和组合物还可用于治疗和预防肾结石、高尿酸血症、痛风和低钠血症。本发明还描述了制备这些化合物的方法。
• SGLT-2 inhibitors, methods of making them, and uses thereof
  申请人：Liu Shuang

  公开号：US08575114B2

  公开（公告）日：2013-11-05

  The present invention relates to compounds which are inhibitors of sodium dependent glucose co-transporter-2 (SGLT-2). These compounds are used in the treatment of various disorders, including diabetes, impaired glucose tolerance, insulin resistance, retinopathy, nephropathy, neuropathy, cataracts, hyperglycemia, hyperinsulinemia, hyperchlolesterolemia, elevated blood level of free fatty acids or glycerol, hyperlipidemia, hypertriglyceridemia, obesity, wound healing, tissue ischemia, atherosclerosis, and hypertension. These compounds and compositions are also useful for treating and preventing kidney stones, hyperuricemia, gout, and hyponatremia. Methods of making these compounds are also described in the present invention.

  本发明涉及一种抑制钠依赖性葡萄糖共转运蛋白-2（SGLT-2）的化合物。这些化合物用于治疗各种疾病，包括糖尿病、糖耐量受损、胰岛素抵抗、视网膜病变、肾病、神经病变、白内障、高血糖、高胰岛素血症、高胆固醇血症、游离脂肪酸或甘油的血液水平升高、高脂血症、高三酰甘油血症、肥胖、创伤愈合、组织缺血、动脉粥样硬化和高血压。这些化合物和组合物还可用于治疗和预防肾结石、高尿酸血症、痛风和低钠血症。本发明还描述了制备这些化合物的方法。
• BICYCLIC TRIAZOLONE DERIVATIVES AND HERBICIDES CONTAINING THE SAME
  申请人：Sumitomo Chemical Takeda Agro Company, Limited

  公开号：EP1333031A1

  公开（公告）日：2003-08-06

  The present invention provides a bicyclic triazolone derivative represented by the formula:         J-Ar     (I) [wherein, J is and Ar is ], which has excellent selective weeding activity and weed killer containing the said bicyclic triazolone derivative.

  本发明提供了一种由式表示的双环三唑酮衍生物： J-Ar (I) [其中，J 是 和 Ar ]，具有优异的选择性除草活性，以及含有上述双环三唑酮衍生物的除草剂。
• US8575114B2
  申请人：——

  公开号：US8575114B2

  公开（公告）日：2013-11-05
• The design and synthesis of novel SGLT2 inhibitors: C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties
  作者：Cheng Guo、Min Hu、Russell J. DeOrazio、Alexander Usyatinsky、Kevin Fitzpatrick、Zhenjun Zhang、Jun-Ho Maeng、Douglas B. Kitchen、Susan Tom、Michele Luche、Yuri Khmelnitsky、Andrew J. Mhyre、Peter R. Guzzo、Shuang Liu

  DOI：10.1016/j.bmc.2014.04.036

  日期：2014.7

  The sodium glucose co-transporter 2 (SGLT2) has received considerable attention in recent years as a target for the treatment of type 2 diabetes mellitus. This report describes the design, synthesis and structure-activity relationship (SAR) of C-glycosides with benzyltriazolopyridinone and phenylhydantoin as the aglycone moieties as novel SGLT2 inhibitors. Compounds 5p and 33b demonstrated high potency in inhibiting SGLT2 and high selectivity against SGLT1. The in vitro ADMET properties of these compounds will also be discussed. (C) 2014 Elsevier Ltd. All rights reserved.