(2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(isoquinolin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 1225430-72-7

• 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-(4-chloro-3-((5-(isoquinolin-3-yl)-1,3,4-thiadiazol-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-3-((5-(isoquinolin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(5-isoquinolin-3-yl-1,3,4-thiadiazol-2-yl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1225430-72-7
• 化学式: C₂₄H₂₂ClN₃O₅S
• 分子量: 499.975
• InChiKey: YTHBFDUHBKYYQI-IFPLKCGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 生成 (2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(isoquinolin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.01.073

文献信息

• NOVEL C-ARYL GLUCOSIDE SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME
  申请人：Lee Jinhwa

  公开号：US20120101051A1

  公开（公告）日：2012-04-26

  A novel C-aryl glucoside compound, or a pharmaceutically acceptable salt or a prodrug thereof 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, are provided.

  提供了一种新型的C-芳基葡萄糖苷化合物，或其药学上可接受的盐或前药，具有抑制肠道和肾脏中存在的钠依赖性葡萄糖共转运体2（SGLT2）的活性；以及包含该化合物作为活性成分的制药组合物，可用于预防或治疗代谢性疾病，特别是糖尿病。
• ADENOSINE DERIVATIVES, METHOD FOR THE SYNTHESIS THEREOF, AND THE PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF THE INFLAMMATORY DISEASES CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：FM Therapeutics Co., Ltd.

  公开号：EP2142549A1

  公开（公告）日：2010-01-13
• US8541380B2
  申请人：——

  公开号：US8541380B2

  公开（公告）日：2013-09-24
• [EN] ADENOSINE DERIVATIVES, METHOD FOR THE SYNTHESIS THEREOF, AND THE PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF THE INFLAMMATORY DISEASES CONTAINING THE SAME AS AN ACTIVE INGREDIENT<br/>[FR] DÉRIVÉS D'ADÉNOSINE, PROCÉDÉ POUR LA SYNTHÈSE DE CES DERNIERS, ET COMPOSITIONS PHARMACEUTIQUES POUR LA PRÉVENTION ET LE TRAITEMENT DE MALADIES INFLAMMATOIRES CONTENANT LESDITS DÉRIVÉS EN TANT QU'INGRÉDIENTS ACTIFS
  申请人：FM THERAPEUTICS CO LTD

  公开号：WO2008108508A1

  公开（公告）日：2008-09-12

  [EN] Disclosed are adenosine derivatives, methods for the synthesis thereof, and pharmaceutical compositions for the prevention and treatment of inflammatory diseases, comprising the same as an active ingredient. The adenosine derivatives have high binding affinity and selectivity for adenosine receptors, especially for A3 adenosine receptors and act as A3 adenosine receptor antagonists, and exhibit anti-inflammatory activity. Thus, the adenosine derivatives are useful in the prevention and treatment of inflammatory diseases.
  [FR] L'invention concerne des dérivés d'adénosine, des procédés pour la synthèse de ces derniers, et des compositions pharmaceutiques pour la prévention et le traitement de maladies inflammatoires contenant lesdits dérivés en tant qu'ingrédients actifs. Lesdits dérivés d'adénosine présentent une haute affinité de liaison aux récepteurs d'adénosine ainsi qu'une sélectivité élevée vis-à-vis de ces derniers, en particulier vis-à-vis des récepteurs A3 de l'adénosine; font office d'antagonistes des récepteurs A3 de l'adénosine; et ont une activité anti-inflammatoire. Par conséquent, lesdits dérivés d'adénosine sont utiles dans la prévention et le traitement de maladies inflammatoires.
• [EN] NOVEL C-ARYL GLUCOSIDE SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME<br/>[FR] NOUVEAUX INHIBITEURS DE SGLT2 CONSISTANT EN C-ARYL GLUCOSIDES ET COMPOSITION PHARMACEUTIQUE LES COMPRENANT
  申请人：GREEN CROSS CORP

  公开号：WO2010147430A2

  公开（公告）日：2010-12-23

  A novel C-aryl glucoside compound, or a pharmaceutically acceptable salt or a prodrug thereof 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, are provided.