4-bromo-2-(4-ethoxybenzyl)-1-methylbenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-2-(4-ethoxybenzyl)-1-methylbenzene
• 英文别名: 1-bromo-3-(4-ethoxybenzyl)-4-methylbenzene；4-bromo-2-[(4-ethoxyphenyl)methyl]-1-methylbenzene
• 化学式: C₁₆H₁₇BrO
• 分子量: 305.214
• InChiKey: MPOCPHMKKBYZMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(4-ethoxybenzyl)-1-methylbenzene 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel C-aryl d-glucofuranosides as sodium-dependent glucose co-transporter 2 inhibitors

  摘要：

  Novel C-aryl-D-glucofuranosides were synthesized and evaluated for their capacity to inhibit human sodium-dependent glucose co-transporter 2 (hSGLT2) and hSGLT1. Compound 21q demonstrated the best in vitro inhibitory activity against SGLT2 in this series (EC50 = 0.62 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.067
• 作为产物：
  描述：

  苯乙醚 在 三乙基硅烷 、 草酰氯 、 三氟化硼乙醚 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-bromo-2-(4-ethoxybenzyl)-1-methylbenzene
  参考文献：
  名称：

  Synthesis and biological evaluation of novel C-aryl d-glucofuranosides as sodium-dependent glucose co-transporter 2 inhibitors

  摘要：

  Novel C-aryl-D-glucofuranosides were synthesized and evaluated for their capacity to inhibit human sodium-dependent glucose co-transporter 2 (hSGLT2) and hSGLT1. Compound 21q demonstrated the best in vitro inhibitory activity against SGLT2 in this series (EC50 = 0.62 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.067

文献信息

• C- ARYL GLYCOSID DERIVATIVES, PHARMACEUTICAL COMPOSITION, PREPARATION PROCESS AND USES THEREOF
  申请人：SHANGHAI DE NOVO PHARMATECH CO. LTD.

  公开号：US20170037038A1

  公开（公告）日：2017-02-09

  This invention relates to a kind of C-aryl glycoside derivatives, its pharmaceutical compositions, preparation methods, and uses thereof. The preparation method comprises: method 1: in a solvent, deprotecting the acetyl protecting groups of compound 1-f in the presence of a base; method 2: 1) compound 2-g reacts with via Mitsunobu reaction; 2) deprotecting the acetyl protecting groups of compound 2-f obtained from step 1; method 3: 1) compound 2-g reacts with via nucleophilic substitution reaction; 2) deprotecting the acetyl protecting groups of compound 3-f obtained from step 1. The pharmaceutical composition comprises a kind of C-aryl glycoside derivatives; it's pharmaceutically acceptable salts and/or prodrugs thereof and excipient thereof. This invention further relates to a kind of C-aryl glycoside derivatives, it's pharmaceutically acceptable salts or pharmaceutical compositions thereof for the use in preparation of a SGLT inhibitor. The C-aryl glycoside derivatives of this invention provides a new direction for the study of SGLT inhibitors.

  这项发明涉及一种C-芳基糖苷衍生物，其药物组合物、制备方法及其用途。制备方法包括：方法1：在溶剂中，在碱的存在下去保护化合物1-f的乙酰保护基；方法2：1）化合物2-g通过Mitsunobu反应发生反应；2）去除从步骤1得到的化合物2-f的乙酰保护基；方法3：1）化合物2-g通过亲核取代反应发生反应；2）去除从步骤1得到的化合物3-f的乙酰保护基。药物组合物包括一种C-芳基糖苷衍生物；其药学上可接受的盐和/或前药以及赋形剂。这项发明还涉及一种C-芳基糖苷衍生物，其药学上可接受的盐或其药物组合物，用于制备SGLT抑制剂。这项发明的C-芳基糖苷衍生物为SGLT抑制剂的研究提供了新的方向。
• (1<i>S</i>)-1,5-Anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-<scp>d</scp>-glucitol (TS-071) is a Potent, Selective Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for Type 2 Diabetes Treatment
  作者：Hiroyuki Kakinuma、Takahiro Oi、Yuko Hashimoto-Tsuchiya、Masayuki Arai、Yasunori Kawakita、Yoshiki Fukasawa、Izumi Iida、Naoko Hagima、Hiroyuki Takeuchi、Yukihiro Chino、Jun Asami、Lisa Okumura-Kitajima、Fusayo Io、Daisuke Yamamoto、Noriyuki Miyata、Teisuke Takahashi、Saeko Uchida、Koji Yamamoto

  DOI：10.1021/jm901893x

  日期：2010.4.22

  Derivatives of a novel scaffold, C-phenyl 1-thio-d-glucitol, were prepared and evaluated for sodium-dependent glucose cotransporter (SGLT) 2 and SGLT1 inhibition activities. Optimization of substituents on the aromatic rings afforded five compounds with potent and selective SGLT2 inhibition activities. The compounds were evaluated for in vitro human metabolic stability, human serum protein binding

  一种新颖的支架的衍生物，c ^ -苯基-1-硫代d -glucitol，制备并评价为钠依赖性葡萄糖协同转运蛋白（SGLT）2个SGLT1抑制活性。优化芳环上的取代基可得到五种具有有效和选择性SGLT2抑制活性的化合物。评价了这些化合物的体外人类代谢稳定性，人类血清蛋白结合（SPB）和Caco-2渗透性。它们中，（1个小号）-1,5-脱水-1- [5-（4-乙氧基苄基）-2-甲氧基-4-甲基苯基] -1-硫代d -glucitol（3P）显示出强效的SGLT2抑制活性（ IC 50 = 2.26 nM），选择性是SGLT1的1650倍。复合3p对冷冻保存的人肝清除率，较低的SPB和适度的Caco-2通透性显示出良好的代谢稳定性。由于3p应该具有可接受的人体药代动力学（PK）特性，因此它可能是治疗2型糖尿病的临床候选药物。我们观察到化合物3p在动物中表现出降血糖作用，出色的尿葡萄糖排泄特性和有
• [EN] SGLT-2 INHIBITORS<br/>[FR] INHIBITEURS DE SGLT-2
  申请人：NAT INST OF BIOLOG SCIENCES BEIJING

  公开号：WO2016041470A1

  公开（公告）日：2016-03-24

  Provided are compounds of SGLT-2 inhibitors, pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

  提供了SGLT-2抑制剂的化合物，以及其药用可接受的盐、氢化物和立体异构体。这些化合物用于制备药物组合物，以及制备和使用方法，包括使用有效量的化合物或组合物治疗需要的人，并检测人体健康或状况的改善。
• Novel <scp>l</scp>-Xylose Derivatives as Selective Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitors for the Treatment of Type 2 Diabetes
  作者：Nicole C. Goodwin、Ross Mabon、Bryce A. Harrison、Melanie K. Shadoan、Zheng Y. Almstead、Yiling Xie、Jason Healy、Lindsey M. Buhring、Christopher M. DaCosta、Jennifer Bardenhagen、Faika Mseeh、Qingyun Liu、Amr Nouraldeen、Alan G. E. Wilson、S. David Kimball、David R. Powell、David B. Rawlins

  DOI：10.1021/jm900951n

  日期：2009.10.22

  The prevalence of diabetes throughout the world continues to increase and has become a major health issue. Recently there have been several reports of inhibitors directed toward the sodium-dependent glucose cotransporter 2 (SGLT2) as a method of maintaining glucose homeostasis in diabetic patients. Herein we report the discovery of the novel O-xyloside 7c that inhibits SGLT2 in vitro and urinary glucose

  全世界的糖尿病患病率持续上升，已经成为一个主要的健康问题。最近，有几篇针对钠依赖性葡萄糖共转运蛋白2（SGLT2）的抑制剂的报道，作为维持糖尿病患者葡萄糖体内稳态的一种方法。在本文中，我们报道了在体外抑制SGLT2和在体内尿葡萄糖重吸收的新型O-木糖苷7c的发现。
• [EN] DIOXA-BICYCLO[3.2.1.]OCTANE-2,3,4-TRIOL DERIVATIVES<br/>[FR] DÉRIVÉS DE DIOXA-BICYCLO[3.2.1.]OCTANE-2,3,4-TRIOL
  申请人：PFIZER

  公开号：WO2010023594A1

  公开（公告）日：2010-03-04

  Compounds of Formula (I) are described herein and the uses thereof for the treatment of diseases, conditions and/or disorders mediated by sodium-glucose transporter inhibitors (in particular, SGLT2 inhibitors).The compounds disclosed herein are useful for the prevention and treatment of obesity and its associated co-morbidities, inn particular type Il (type 2) diabetes.

  本文描述了化合物(I)的结构式及其用途，用于治疗由钠葡萄糖转运体抑制剂（特别是SGLT2抑制剂）介导的疾病、状况和/或紊乱。本文披露的化合物对于预防和治疗肥胖及其相关的共病症特别是II型（2型）糖尿病具有用处。