4-Isocyanatomethyl-1,2-dimethyl-benzene | 916646-43-0

• 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-Isocyanatomethyl-1,2-dimethyl-benzene
• 英文别名: 4-(Isocyanatomethyl)-1,2-dimethylbenzene；4-(isocyanatomethyl)-1,2-dimethylbenzene
• CAS: 916646-43-0
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: VUGOJLCSMBEXRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Isocyanatomethyl-1,2-dimethyl-benzene 在 4-二甲氨基吡啶 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 4-[1-(3,4-Dimethyl-benzylcarbamoyl)-3,3-diethyl-4-oxo-azetidin-2-yloxy]-benzoic acid
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  (3,4-Dimethyl-phenyl)-acetylchlorid 在 sodium azide 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 1.0h， 生成 4-Isocyanatomethyl-1,2-dimethyl-benzene
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003

文献信息

• AZOLOPYRIDIN-2-ONE DERIVATIVES AS LIPASE AND PHOSPHOLIPASE INHIBITORS
  申请人：ZOLLER Gerhard

  公开号：US20080167339A1

  公开（公告）日：2008-07-10

  The present invention provides compounds which have an inhibitory effect on hormone-sensitive lipase or endothelial lipase. The compounds of the invention are azolopyridin-2-one derivatives of the general formula I wherein the substituents are as defined herein. The compounds of formula I wherein R2 is hydrogen are distinguished by favorable effects on disorders of lipid metabolism. They beneficially influence the HDL to LDL ratio and increase in particular the HDL level and are suitable for the prevention and treatment of dyslipidemias and metabolic syndrome and their diverse sequelae such as atherosclerosis, coronary heart disease, heart failure, obesity and diabetes. The compounds of formula I wherein R1 and R2 together form a ring system are distinguished by favorable effects on metabolic disorders. They beneficially influence lipid and sugar metabolism; in particular they lower the triglyceride level and are suitable for the prevention and treatment of type II diabetes and arteriosclerosis and the diverse sequelae thereof.

  本发明提供了具有抑制激素敏感性脂肪酶或内皮脂肪酶作用的化合物。本发明的化合物是一般式I的唑啉吡啶-2-酮衍生物，其中置换基如本文所定义。当R2为氢时，式I的化合物具有有利的脂质代谢紊乱影响。它们有益地影响HDL与LDL比率，特别是增加HDL水平，并适用于预防和治疗脂质代谢紊乱和代谢综合征及其多种后遗症，如动脉粥样硬化、冠心病、心力衰竭、肥胖症和糖尿病。当R1和R2一起形成环系统时，式I的化合物具有有利的代谢紊乱影响。它们有益地影响脂质和糖代谢；特别是降低三酰甘油水平，并适用于预防和治疗II型糖尿病和动脉硬化及其多种后遗症。
• AZOLOPYRIDIN-2-ON-DERIVATE ALS INHIBITOREN VON LIPASEN UND PHOSPHOLIPASEN
  申请人：Sanofi-Aventis

  公开号：EP1896485A1

  公开（公告）日：2008-03-12
• LÖSEMITTELARME BESCHICHTUNGSSYSTEME FÜR TEXTILIEN
  申请人：Covestro Deutschland AG

  公开号：EP3568423A1

  公开（公告）日：2019-11-20
• BESTÄNDIGE 2K-PUR-BESCHICHTUNGEN
  申请人：Covestro Intellectual Property GmbH & Co. KG

  公开号：EP3994192A1

  公开（公告）日：2022-05-11
• VERFAHREN ZUR HERSTELLUNG VON ISOCYANURATEN AUS URETDIONEN
  申请人：Covestro Intellectual Property GmbH & Co. KG

  公开号：EP3997183A1

  公开（公告）日：2022-05-18