(2R3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)tetrahydro-2H-pyran | 1259018-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)tetrahydro-2H-pyran
• 英文别名: (2R,3R,4R,5S,6S)-3,4,5-Tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)tetrahydro-2H-pyran；(2S,3S,4R,5R,6R)-2-[3-(bromomethyl)-4-chlorophenyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1259018-17-1
• 化学式: C₄₁H₄₀BrClO₅
• 分子量: 728.123
• InChiKey: IURHZFNAAZOORF-XGLMOPDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)tetrahydro-2H-pyran 在 bis-triphenylphosphine-palladium(II) chloride 、 三氯化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 (2S,3R,4R,5S,6R)-2-(4-chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  JP5876570

  摘要：

  公开号：
• 作为产物：
  描述：

  (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol 在 吡啶 、 lithium hydroxide monohydrate 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 36.0h， 生成 (2R3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-(bromomethyl)-4-chlorophenyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  JP5876570

  摘要：

  公开号：

文献信息

• NOVEL DIPHENYLMETHANE DERIVATIVES AS SGLT2 INHIBITORS
  申请人：Choi Soongyu

  公开号：US20140088079A1

  公开（公告）日：2014-03-27

  The present invention relates to a compound with a diphenylmethane moiety 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. The present invention also provides a method for preparing the compound, and a method for preventing or treating metabolic disorders, particularly diabetes, by using the compound.

  本发明涉及一种具有二苯甲烷基团的化合物，其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，尤其是糖尿病。本发明还提供了一种制备该化合物的方法，以及使用该化合物预防或治疗代谢性疾病，尤其是糖尿病的方法。
• Diphenylmethane derivatives as SGLT2 inhibitors
  申请人：GREEN CROSS CORPORATION

  公开号：US09371303B2

  公开（公告）日：2016-06-21

  A compound with a diphenylmethane moiety having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney is disclosed. A pharmaceutical composition including the compound as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly diabetes is disclosed. A method for preparing the compound, and a method for preventing or treating metabolic disorders, particularly diabetes, by using the compound is provided.

  本发明揭示了一种含有二苯甲烷基团的化合物，该化合物具有抑制存在于肠和肾中的钠依赖性葡萄糖共转运体2（SGLT2）的活性。本发明还揭示了一种包括该化合物作为活性成分的制药组合物，该组合物可用于预防或治疗代谢紊乱，特别是糖尿病。本发明还提供了一种制备该化合物的方法，以及使用该化合物预防或治疗代谢紊乱，特别是糖尿病的方法。
• Synthesis and biological evaluation of C-glucosides with azulene rings as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus: Discovery of YM543
  作者：Kazuhiro Ikegai、Masakazu Imamura、Takayuki Suzuki、Keita Nakanishi、Takeshi Murakami、Eiji Kurosaki、Atsushi Noda、Yoshinori Kobayashi、Masayuki Yokota、Tomokazu Koide、Kazuhiro Kosakai、Yasufumi Ohkura、Makoto Takeuchi、Hiroshi Tomiyama、Mitsuaki Ohta

  DOI：10.1016/j.bmc.2013.03.067

  日期：2013.7

  Here, a series of C-glucosides with azulene rings in the aglycon moiety was synthesized and the inhibitory activities toward hSGLT1 and hSGLT2 were evaluated. Starting from the azulene derivative 7 which had relatively good SGLT2 inhibitory activity, compound 8a which has a 3-[(azulen-2-yl)methyl]phenyl group was identified as a lead compound for further optimization. Introduction of a phenolic hydroxyl group onto the central benzene ring afforded a potent and selective SGLT2 inhibitor 8e, which reduced blood glucose levels in a dose-dependent manner in rodent diabetic models. A mono choline salt of 8e (YM543) was selected as a clinical candidate for use in treating type 2 diabetes mellitus. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners
  作者：Junwon Lee、Sung-Han Lee、Hee Jeong Seo、Eun-Jung Son、Suk Ho Lee、Myung Eun Jung、MinWoo Lee、Ho-Kyun Han、Jeongmin Kim、Jahyo Kang、Jinhwa Lee

  DOI：10.1016/j.bmc.2010.01.073

  日期：2010.3

  Novel C-aryl glucoside SGLT2 inhibitors containing 1,3,4-thiadiazole moieties were designed and synthesized. Among the compounds tested, biaryl-type compounds containing pyrazine 59, 2-furan 61, and 3-thiophene 71 showed the best in vitro inhibitory activities to date (IC50 = 3.51-7.03 nM) against SGLT2. A selected compound 61, demonstrated reasonable blood glucose-lowering effects, indicating that the information obtained from the SAR studies in this 1,3,4-thiadiazolylmethylphenyl glucoside series might help to design more active SGLT2 inhibitors that are structurally related. (C) 2010 Elsevier Ltd. All rights reserved.
• Pyrimidinylmethylphenyl glucoside as novel C-aryl glucoside SGLT2 inhibitors
  作者：Junwon Lee、Jong Yup Kim、Jungsub Choi、Sung-Han Lee、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmcl.2010.09.103

  日期：2010.12

  Novel C-aryl glucoside SGLT2 inhibitors containing pyrimidine motif were designed and synthesized for biological evaluation. Among the compounds assayed, pyrimidine containing methylthio moiety 11g demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date (IC50 = 10.7 nM). (C) 2010 Elsevier Ltd. All rights reserved.