4-N,N-dimethylaminosulfonylphenylacetic acid ethyl ester | 1221446-19-0

• 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-N,N-dimethylaminosulfonylphenylacetic acid ethyl ester
• 英文别名: Ethyl 2-[4-(dimethylsulfamoyl)phenyl]acetate
• CAS: 1221446-19-0
• 化学式: C₁₂H₁₇NO₄S
• 分子量: 271.337
• InChiKey: ZCQNTZIUHGBWLI-UHFFFAOYSA-N

物化性质

• 沸点：
  378.3±44.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘甲基环戊烷 、 4-N,N-dimethylaminosulfonylphenylacetic acid ethyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 杀扑磷 为溶剂， 反应 15.25h， 生成 Ethyl 3-cyclopentyl-2-[4-(dimethylsulfamoyl)phenyl]propanoate
  参考文献：
  名称：

  Investigation of Functionally Liver Selective Glucokinase Activators for the Treatment of Type 2 Diabetes

  摘要：

  Type 2 diabetes is a polygenic disease which afflicts nearly 200 million people worldwide and is expected to increase to near epidemic levels over the next 10-15 years. Glucokinase (GK) activators are currently under investigation by a number of pharmaceutical companies with only a few reaching early clinical evaluation. A GK activator has the promise of potentially affecting both the beta-cells of the pancreas, by improving glucose sensitive insulin secretion, as well as the liver, by reducing uncontrolled glucose output and restoring post-prandial glucose uptake and storage as glycogen. Herein, we report our efforts on a sulfonamide chemotype with the aim to generate liver selective GK activators which culminated in the discovery of 3-cyclopentyl-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-2-[4-(4-methylpiperazine-1-sulfonyl)-phenyl]-propionamide (17c). This compound activated the GK enzyme (alpha K(a) = 39 nM) in vitro at low nanomolar concentrations and significantly reduced glucose levels during an oral glucose tolerance test in normal mice.

  DOI：

  10.1021/jm900839k
• 作为产物：
  描述：

  苯乙酸乙酯 、 二甲胺 在 氯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 、 4-N,N-dimethylaminosulfonylphenylacetic acid ethyl ester
  参考文献：
  名称：

  Investigation of Functionally Liver Selective Glucokinase Activators for the Treatment of Type 2 Diabetes

  摘要：

  Type 2 diabetes is a polygenic disease which afflicts nearly 200 million people worldwide and is expected to increase to near epidemic levels over the next 10-15 years. Glucokinase (GK) activators are currently under investigation by a number of pharmaceutical companies with only a few reaching early clinical evaluation. A GK activator has the promise of potentially affecting both the beta-cells of the pancreas, by improving glucose sensitive insulin secretion, as well as the liver, by reducing uncontrolled glucose output and restoring post-prandial glucose uptake and storage as glycogen. Herein, we report our efforts on a sulfonamide chemotype with the aim to generate liver selective GK activators which culminated in the discovery of 3-cyclopentyl-N-(5-methoxy-thiazolo[5,4-b]pyridin-2-yl)-2-[4-(4-methylpiperazine-1-sulfonyl)-phenyl]-propionamide (17c). This compound activated the GK enzyme (alpha K(a) = 39 nM) in vitro at low nanomolar concentrations and significantly reduced glucose levels during an oral glucose tolerance test in normal mice.

  DOI：

  10.1021/jm900839k

文献信息

• AMIDE COMPOUNDS, THEIR PHARMACEUTICAL COMPOSITIONS, THEIR PREPARATION METHOD AND THEIR USES
  申请人：Long Yaqiu

  公开号：US20110251192A1

  公开（公告）日：2011-10-13

  The present invention pertains to the field of pharmaceutical chemistry and discloses 8-(3-aminopropyl)-3-exo-8-azabicyclo[3.2.1]octane-3-amino amide compounds represented by formula I, the pharmaceutical compositions, the preparation method and the use thereof. Such compounds or pharmaceutically acceptable salts thereof can be used as an antagonist of CCR5 in preparing medicaments for treating diseases mediated by CCR5, particularly HIV infection, asthma, rheumatoid arthritis, autoimmune diseases and chronic obstructive pulmonary diseases (COPD).

  本发明涉及制药化学领域，揭示了由式I代表的8-(3-氨丙基)-3-外消旋-8-氮杂双环[3.2.1]辛烷-3-氨基酰胺化合物，以及药物组合物、制备方法和使用方法。这些化合物或其药用可接受盐可用作CCR5的拮抗剂，用于制备治疗由CCR5介导的疾病的药物，特别是HIV感染、哮喘、类风湿性关节炎、自身免疫疾病和慢性阻塞性肺病（COPD）的药物。
• US8410094B2
  申请人：——

  公开号：US8410094B2

  公开（公告）日：2013-04-02