4-nitrobenzoic acid 3-hydroxyphenyl ester | 89683-24-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-nitrobenzoic acid 3-hydroxyphenyl ester
• 英文别名: 4-Nitro-benzoesaeure-(3-hydroxy-phenylester)；1,3-Benzenediol, O-(4-nitrobenzoyl)-；(3-hydroxyphenyl) 4-nitrobenzoate
• CAS: 89683-24-9
• 化学式: C₁₃H₉NO₅
• 分子量: 259.218
• InChiKey: DSCNNRWYLGTNDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 间苯二酚 在 三乙胺 作用下， 以 丙酮 为溶剂， 以80%的产率得到4-nitrobenzoic acid 3-hydroxyphenyl ester
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of new HSL inhibitors guided by pharmacophore models

  摘要：

  Hormone-sensitive lipase (HSL) is a critical enzyme involved in the hormonally regulated release of fatty acids and glycerol from adipocyte lipid stores. Its inhibition may improve insulin sensitivity and blood glucose handling in type 2 diabetes. Accordingly, many small-molecule HSL inhibitors have recently been identified. In continuation of our efforts for discovery of new HSL inhibitors, we prepared a variety of esters, amides, sulfonamides and sulfonate esters capable of fitting two pharmacophore models that we developed and published earlier. The tested compounds were synthesized via coupling reactions of aroyl chlorides or sulfonyl chlorides with phenols, amines and related derivatives. Our efforts led to the identification of interesting compounds of low micromolar anti-HSL bioactivities, which have potential to be developed into effective antidiabetic agents.

  DOI：

  10.1007/s00044-013-0616-2

文献信息

• Chemotherapeutic Study of p-Nitrobenzoyl- and Related Compounds
  作者：C. Siebenmann、R. J. Schnitzer

  DOI：10.1021/ja01251a029

  日期：1943.11
• Design, synthesis and structure–activity relationship of new HSL inhibitors guided by pharmacophore models
  作者：Jumana D. Al-Shawabkeh、Afaf H. Al-Nadaf、Lina A. Dahabiyeh、Mutasem O. Taha

  DOI：10.1007/s00044-013-0616-2

  日期：2014.1

  Hormone-sensitive lipase (HSL) is a critical enzyme involved in the hormonally regulated release of fatty acids and glycerol from adipocyte lipid stores. Its inhibition may improve insulin sensitivity and blood glucose handling in type 2 diabetes. Accordingly, many small-molecule HSL inhibitors have recently been identified. In continuation of our efforts for discovery of new HSL inhibitors, we prepared a variety of esters, amides, sulfonamides and sulfonate esters capable of fitting two pharmacophore models that we developed and published earlier. The tested compounds were synthesized via coupling reactions of aroyl chlorides or sulfonyl chlorides with phenols, amines and related derivatives. Our efforts led to the identification of interesting compounds of low micromolar anti-HSL bioactivities, which have potential to be developed into effective antidiabetic agents.