3-(2-methyl-3-hydroxypropyl)-4-(pivaloyloxy)benzophenone | 112005-10-4

• 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: 3-(2-methyl-3-hydroxypropyl)-4-(pivaloyloxy)benzophenone
• 英文别名: 3-(2-Methyl-3-hydroxypropyl)-4-pivaloyloxybenzophenone；[4-benzoyl-2-(3-hydroxy-2-methylpropyl)phenyl] 2,2-dimethylpropanoate
• CAS: 112005-10-4
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: YDJUXRPEULXZFF-UHFFFAOYSA-N

物化性质

• 沸点：
  508.8±50.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methyl-3-hydroxypropyl)-4-(pivaloyloxy)benzophenone 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 3-(2-formylpropyl)-4-(pivaloyloxy)benzophenone
  参考文献：
  名称：

  (Acyloxy)benzophenones and (acyloxy)-4-pyrones. A new class of inhibitors of human neutrophil elastase

  摘要：

  A series of 4-(acyloxy)- and 4,4'-bis(acyloxy)benzophenones were synthesized. Some of them, pivalates (trimethylacetates) and isobutyrates in particular, were found to be potent and selective inhibitors of human neutrophil (leukocyte) elastase. A series of 2-[(acyloxy)methyl]-5-(acyloxy)-4-pyrones were synthesized regioselectively from kojic acid. The 4-pyrones bearing a long chain acyl group at the 2-position and either pivaloyloxy or isobutyryloxy at the 5-position were potent and selective inhibitors of the human elastase. A number of analogues and derivatives in both series were synthesized in order to study the structure-activity relationship as summarized in Tables I-VI and in Tables IX and X. The inhibition was selective to human neutrophil elastase. No inhibition of porcine pancreatic elastase or bovine pancreatic chymotrypsin (Tables VII and XI) was observed. The most likely mechanism of inhibition is discussed. The implication of these findings for the treatment of rheumatoid arthritis and emphysema is outlined.

  DOI：

  10.1021/jm00400a030
• 作为产物：
  描述：

  4-羟基-二苯甲酮 在 吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 potassium carbonate 、 N,N-二乙基苯胺 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 107.5h， 生成 3-(2-methyl-3-hydroxypropyl)-4-(pivaloyloxy)benzophenone
  参考文献：
  名称：

  (Acyloxy)benzophenones and (acyloxy)-4-pyrones. A new class of inhibitors of human neutrophil elastase

  摘要：

  A series of 4-(acyloxy)- and 4,4'-bis(acyloxy)benzophenones were synthesized. Some of them, pivalates (trimethylacetates) and isobutyrates in particular, were found to be potent and selective inhibitors of human neutrophil (leukocyte) elastase. A series of 2-[(acyloxy)methyl]-5-(acyloxy)-4-pyrones were synthesized regioselectively from kojic acid. The 4-pyrones bearing a long chain acyl group at the 2-position and either pivaloyloxy or isobutyryloxy at the 5-position were potent and selective inhibitors of the human elastase. A number of analogues and derivatives in both series were synthesized in order to study the structure-activity relationship as summarized in Tables I-VI and in Tables IX and X. The inhibition was selective to human neutrophil elastase. No inhibition of porcine pancreatic elastase or bovine pancreatic chymotrypsin (Tables VII and XI) was observed. The most likely mechanism of inhibition is discussed. The implication of these findings for the treatment of rheumatoid arthritis and emphysema is outlined.

  DOI：

  10.1021/jm00400a030

文献信息

• Phenolic ester derivatives as elastase inhibitors
  申请人：G. D. Searle & Co.

  公开号：US04683241A1

  公开（公告）日：1987-07-28

  Phenolic esters of the general formula I ##STR1## are useful for the prevention, management or alleviation of elastase mediated diseases or conditions.

  通式I的酚酯##STR1##可用于预防、管理或缓解弹性蛋白酶介导的疾病或症状。
• MIYANO, MASATERU;DEASON, JAMES R.
  作者：MIYANO, MASATERU、DEASON, JAMES R.

  DOI：——

  日期：——
• MIYANO, MASATERU;DEASON, JAMES R.;NAKAO, AKIRA;STEALEY, MICHAEL A.;VILLAM+, J. MED. CHEM., 31,(1988) N 5, 1052-1061
  作者：MIYANO, MASATERU、DEASON, JAMES R.、NAKAO, AKIRA、STEALEY, MICHAEL A.、VILLAM+

  DOI：——

  日期：——
• US4683241A
  申请人：——

  公开号：US4683241A

  公开（公告）日：1987-07-28
• US4801610A
  申请人：——

  公开号：US4801610A

  公开（公告）日：1989-01-31