(5-溴-2-氯-4-甲氧基苯基)(4-乙氧基苯基)甲酮 | 1006590-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5-溴-2-氯-4-甲氧基苯基)(4-乙氧基苯基)甲酮
• 英文名称: (5-bromo-2-chloro-4-methoxyphenyl)(4-ethoxyphenyl)methanone
• 英文别名: (5-Bromo-2-chloro-4-methoxyphenyl)(4-ethoxyphenyl)methanone；(5-bromo-2-chloro-4-methoxyphenyl)-(4-ethoxyphenyl)methanone
• CAS: 1006590-10-8
• 化学式: C₁₆H₁₄BrClO₃
• 分子量: 369.642
• InChiKey: OUKPQOYRNHOZIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-溴-2-氯-4-甲氧基苯基)(4-乙氧基苯基)甲酮 在 三乙基硅烷 、 正丁基锂 、 甲烷磺酸 、 三氟化硼乙醚 、 potassium carbonate 、 乙硫醇钠 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 10.5h， 生成 (3R,4S,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents

  摘要：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50 = 0.778 nM and 23, IC50 = 0.899 nM) against hSGLT2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.045
• 作为产物：
  描述：

  2-氯-4-羟基苯甲腈 在 aluminum (III) chloride 、 氯化亚砜 、 lithium hydroxide monohydrate 、 三氟甲磺酸 、 水 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 27.17h， 生成 (5-溴-2-氯-4-甲氧基苯基)(4-乙氧基苯基)甲酮
  参考文献：
  名称：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents

  摘要：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50 = 0.778 nM and 23, IC50 = 0.899 nM) against hSGLT2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.045

文献信息

• NOVEL C-ARYL ANSA SGLT2 INHIBITORS
  申请人：Kim Min Ju

  公开号：US20140213642A1

  公开（公告）日：2014-07-31

  Disclosed is a novel C-aryl ansa compound 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. Also provided are a method for preparing the compound, and a method for preventing or treating metabolic disorders, particularly diabetes, by using the compound.

  本发明涉及一种新的C-芳基ansa化合物，具有抑制肠和肾中存在的钠依赖性葡萄糖转运蛋白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，该组合物对预防或治疗代谢紊乱，特别是糖尿病有用。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。
• C-aryl ansa SGLT2 inhibitors
  申请人：Kim Min Ju

  公开号：US08921412B2

  公开（公告）日：2014-12-30

  Disclosed is a novel C-aryl ansa compound 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. Also provided are a method for preparing the compound, and a method for preventing or treating metabolic disorders, particularly diabetes, by using the compound.

  本发明公开了一种新的C-芳基ansa化合物，其具有对存在于肠和肾中的钠依赖性葡萄糖转运蛋白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，可用于预防或治疗代谢性疾病，特别是糖尿病。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，特别是糖尿病的方法。
• Synthesis and biological evaluation of novel C-aryl d-glucofuranosides as sodium-dependent glucose co-transporter 2 inhibitors
  作者：Tzung-Sheng Lin、Ya-Wen Liw、Jen-Shin Song、Tsung-Chih Hsieh、Hsien-Wei Yeh、Lih-Ching Hsu、Chun-Jung Lin、Szu-Huei Wu、Pi-Hui Liang

  DOI：10.1016/j.bmc.2013.08.067

  日期：2013.11

  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.
• US8921412B2
  申请人：——

  公开号：US8921412B2

  公开（公告）日：2014-12-30
• [EN] NOVEL C-ARYL ANSA SGLT2 INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS C-ARYLE ANSA DE SGLT2
  申请人：GREEN CROSS CORP

  公开号：WO2012173410A2

  公开（公告）日：2012-12-20

  The present invention relates to a novel C-aryl ansa compound 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.