N-(2-hydroxypropyl)-4-methylbenzamide | 880080-66-0

• 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: N-(2-hydroxypropyl)-4-methylbenzamide
• CAS: 880080-66-0
• 化学式: C₁₁H₁₅NO₂
• mdl: MFCD00485321
• 分子量: 193.246
• InChiKey: NHVKSUKFAMAWSE-UHFFFAOYSA-N

物化性质

• 沸点：
  382.0±35.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxypropyl)-4-methylbenzamide 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以71%的产率得到N-acetonyl-4-methylbenzamide
  参考文献：
  名称：

  Structure–activity studies on 1,3-dioxane-2-carboxylic acid derivatives, a novel class of subtype-selective peroxisome proliferator-activated receptor α (PPARα) agonists

  摘要：

  A series of 1,3-dioxane carboxylic acid derivatives was synthesized and evaluated for human PPAR transactivation activity. Structure-activity relationships on the phenyloxazole moiety of the lead compound 3 revealed that the introduction of small hydrophobic substituents at the 4-position of the terminal phenyl ring increased the PPAR alpha agonist activity, and that the oxazole heterocycle was essential to the maintenance of both potency and PPAR alpha subtype-selectivity. This investigation led to the identification of 14d (NS-220) and 14i as highly potent and selective human PPAR alpha agonists. In KK-A(y) type 2 diabetic mice, these compounds significantly lowered plasma triglyceride and very-low-density plus low-density lipoprotein cholesterol levels while simultaneously raising HDL cholesterol levels. Our results suggest that highly potent and subtype-selective PPAR alpha agonists will be promising drugs for the treatment of metabolic disorders in type 2 diabetes. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.007
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 异丙醇胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以71%的产率得到N-(2-hydroxypropyl)-4-methylbenzamide
  参考文献：
  名称：

  Structure–activity studies on 1,3-dioxane-2-carboxylic acid derivatives, a novel class of subtype-selective peroxisome proliferator-activated receptor α (PPARα) agonists

  摘要：

  A series of 1,3-dioxane carboxylic acid derivatives was synthesized and evaluated for human PPAR transactivation activity. Structure-activity relationships on the phenyloxazole moiety of the lead compound 3 revealed that the introduction of small hydrophobic substituents at the 4-position of the terminal phenyl ring increased the PPAR alpha agonist activity, and that the oxazole heterocycle was essential to the maintenance of both potency and PPAR alpha subtype-selectivity. This investigation led to the identification of 14d (NS-220) and 14i as highly potent and selective human PPAR alpha agonists. In KK-A(y) type 2 diabetic mice, these compounds significantly lowered plasma triglyceride and very-low-density plus low-density lipoprotein cholesterol levels while simultaneously raising HDL cholesterol levels. Our results suggest that highly potent and subtype-selective PPAR alpha agonists will be promising drugs for the treatment of metabolic disorders in type 2 diabetes. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.007

文献信息

• [EN] NOVEL DIOL COMPOUNDS SYNTHESIS AND ITS USE FOR FORMAL SYNTHESIS OF (2R, 3 S)-3-HYDROXYPIPECOLIC ACID<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE NOUVEAUX COMPOSÉS DE DIOL ET SON UTILISATION POUR LA SYNTHÈSE FORMELLE D'ACIDE (2R, 3S)-3-HYDROXYPIPÉCOLIQUE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016056031A1

  公开（公告）日：2016-04-14

  The patent discloses novel diol derivatives of general formula I, [Formula should be inserted here] A chiral pool process for the synthesis of the compound of formula I from D glucose. Further, it discloses a process for the synthesis of (2R, 3S)-3-hydroxypipecolic acid from D- glucose using chiral pool approach, wherein the D-glucose used is in enantiomerically pure form.

  该专利披露了一种通式I的新型二醇衍生物，[此处应插入公式] 从D-葡萄糖开始合成公式I化合物的手性池方法。此外，它还披露了一种从D-葡萄糖使用手性池方法合成(2R,3S)-3-羟基哌酸的过程，其中使用的D-葡萄糖为对映纯形式。
• NOVEL OXADIAZOLE DERIVATIVE AND PHARMACEUTICAL CONTAINING SAME
  申请人：National Center for Geriatrics and Gerontology

  公开号：EP3275440B1

  公开（公告）日：2022-05-04
• [EN] PROCESS FOR PRODUCTION OF HETEROCYCLIC COMPOUNDS<br/>[FR] PROCEDE DE PRODUCTION DE COMPOSES HETEROCYCLIQUES
  申请人：NIPPON SHINYAKU CO LTD

  公开号：WO2006030892A1

  公开（公告）日：2006-03-23

  　本発明は、工業スケールでの大量合成に適した、ＮＳ－２２０の製造方法を提供することにある。　本発明は、（１）メチル　５－（４－クロロブチル）－２－メチル－１，３－ジオキサン－２－カルボキシレートのシス－トランス混合物を、塩基存在下で加水分解することを特徴とする、メチル　シス－５－（４－クロロブチル）－２－メチル－１，３－ジオキサン－２－カルボキシレートの製造方法、（２）４－メチル－Ｎ－（２－ヒドロキシプロピル）ベンズアミドを２，２，６，６－テトラメチル－１－ピペリジニルオキシラジカル及び次亜塩素酸ナトリウムを用いて酸化することを特徴とする、４－メチル－Ｎ－（２－オキソプロピル）ベンズアミドの製造方法、などで構成される。
• Structure–activity studies on 1,3-dioxane-2-carboxylic acid derivatives, a novel class of subtype-selective peroxisome proliferator-activated receptor α (PPARα) agonists
  作者：Tetsuo Asaki、Tomiyoshi Aoki、Taisuke Hamamoto、Yukiteru Sugiyama、Shinji Ohmachi、Kenji Kuwabara、Kohji Murakami、Makoto Todo

  DOI：10.1016/j.bmc.2007.10.007

  日期：2008.1

  A series of 1,3-dioxane carboxylic acid derivatives was synthesized and evaluated for human PPAR transactivation activity. Structure-activity relationships on the phenyloxazole moiety of the lead compound 3 revealed that the introduction of small hydrophobic substituents at the 4-position of the terminal phenyl ring increased the PPAR alpha agonist activity, and that the oxazole heterocycle was essential to the maintenance of both potency and PPAR alpha subtype-selectivity. This investigation led to the identification of 14d (NS-220) and 14i as highly potent and selective human PPAR alpha agonists. In KK-A(y) type 2 diabetic mice, these compounds significantly lowered plasma triglyceride and very-low-density plus low-density lipoprotein cholesterol levels while simultaneously raising HDL cholesterol levels. Our results suggest that highly potent and subtype-selective PPAR alpha agonists will be promising drugs for the treatment of metabolic disorders in type 2 diabetes. (C) 2007 Elsevier Ltd. All rights reserved.