N-acetonyl-4-methoxybenzamide | 1016572-15-8

• 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-acetonyl-4-methoxybenzamide
• 英文别名: 4-methoxy-N-(2-oxopropyl)benzamide
• CAS: 1016572-15-8
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: UJXLTWALQFNGFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  伯吉斯试剂 、 N-acetonyl-4-methoxybenzamide 在 氮气 、 乙酸乙酯 、 Brine 、 magnesium sulfate 、 silica gel 、 正己烷 作用下， 以 四氢呋喃 、 Brine 为溶剂， 反应 1.0h， 以to give the title compound (530 mg) as a colorless oil的产率得到2-(4-Methoxyphenyl)-5-methyloxazole
  参考文献：
  名称：

  SULFONAMIDE DERIVATIVE AND USE THEREOF

  摘要：

  提供了一种具有AMPA受体功能增强作用的化合物，可用作预防或治疗抑郁症、阿尔茨海默病、精神分裂症、注意力缺陷多动障碍（ADHD）等药物。该化合物由式（I）表示：其中每个符号如本说明书所定义，或其盐。

  公开号：

  US20140024650A1
• 作为产物：
  描述：

  N-(2-hydroxypropyl)-4-methoxybenzamide 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到N-acetonyl-4-methoxybenzamide
  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

• Heterocyclic compounds
  申请人：——

  公开号：US20030166697A1

  公开（公告）日：2003-09-04

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1], or a pharmaceutically acceptable salt thereof: R 1 -Het-D-E  [1] wherein: R 1 is optionally substituted aryl or aromatic heterocyclic group, Het is a divalent aromatic heterocyclic group, D is alkylene, alkenylene, alkynylene, or the like, and E is carboxy, or the like, and novel compounds among the heterocyclic compounds of the formula [1] above, which has blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种用于高脂血症的预防或治疗剂，其活性成分为式[1]所示的杂环化合物或其药学上可接受的盐：R1-Het-D-E [1]其中：R1为任选取代的芳基或芳香性杂环基团，Het为二价芳香性杂环基团，D为亚烷基、亚烯基、亚炔基等，E为羧基等，以及上述式[1]所示杂环化合物中的新型化合物，其具有降低血液甘油三酯、降低LDL-C、降低血糖、降低血液胰岛素、增加HDL-C或降低动脉粥样硬化指数的效果，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖等疾病。
• AROMATIC AMINE AR AND BET TARGETING PROTEIN DEGRADATION CHIMERA COMPOUND AND USE
  申请人：Hinova Pharmaceuticals Inc.

  公开号：EP3971176A1

  公开（公告）日：2022-03-23

  An aromatic amine androgen receptor (AR) and BET targeting protein degradation chimera compound and its use. Specifically provided is a compound represented by formula I. Experimental results show that the compound can target and degrade both AR and BRD4, and down-regulate the expression of AR and BRD4 proteins; the compound can inhibit the proliferation of a variety of prostate cancer cells; the compound can inhibit the proliferation of a prostate cancer cell line LNCaP/AR, which overexpresses the AR, and can achieve a good inhibition effect on a prostate cancer cell line 22RV1, which is resistant to a marketed prostate cancer drug (enzalutamide); the compound also shows good metabolic stability, and has a good application prospect in the preparation of an AR and/or BET protein degradation targeting chimera, and a drug for the treatment of related diseases regulated by the AR and BET.

  一种芳香胺雄激素受体（AR）和BET靶向蛋白降解嵌合物化合物及其用途。具体提供的是由式I表示的化合物。实验结果表明，该化合物可以靶向降解AR和BRD4，并下调AR和BRD4蛋白的表达；该化合物可以抑制多种前列腺癌细胞的增殖；该化合物可以抑制过表达AR的前列腺癌细胞系LNCaP/AR的增殖，并且对一种对市售前列腺癌药物（恩扎鲁胺）具有耐药性的前列腺癌细胞系22RV1具有良好的抑制效果；该化合物还表现出良好的代谢稳定性，在制备AR和/或BET蛋白降解靶向嵌合物和治疗由AR和BET调控的相关疾病的药物方面具有良好的应用前景。
• HETEROCYCLIC COMPOUNDS
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP1295875A1

  公开（公告）日：2003-03-26

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1] or a pharmaceutically acceptable salt thereof:         R1―Het―D―E     [1] wherein: R1 is optionally substituted aryl or aromatic heterocyclic group, Het is a divalent aromatic heterocyclic group, D is alkylene, alkenylene, alkynylene, or the like, and E is carboxy, or the like, and novel compounds among the heterocyclic compounds of the formula [1] above, which has blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种预防或治疗高脂血症的药物，其活性成分包括式 [1] 的杂环化合物或其药学上可接受的盐： R1-Het-D-E [1] 其中 R1为任选取代的芳基或芳香杂环基团，Het为二价芳香杂环基团，D为亚烷基、亚烯基、亚炔基或类似基团，E为羧基或类似基团，上述式[1]杂环化合物中的新型化合物，具有降血甘油三酯作用、低密度脂蛋白胆固醇（LDL-C）降低效果、血糖降低效果和血胰岛素降低效果，或高密度脂蛋白胆固醇（HDL-C）增加效果或动脉粥样硬化指数降低效果，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖症等。
• Heterocyclic compounds for the treatment of hyperlipidemia agents
  申请人：Nippon Shinyaku Co., Ltd.

  公开号：EP1634876A2

  公开（公告）日：2006-03-15

  The present invention provides a preventive or therapeutic agent for hyperlipidemia, comprising as an active ingredient a heterocyclic compound of the formula [1] or a pharmaceutically acceptable salt thereof:         R 1 -Het-D-E     [1] The preventive or therapeutic agent has a blood triglyceride lowering effect, LDL-C lowering effect, and blood glucose lowering effect and blood insulin lowering effect, or HDL-C increasing effect or atherogenic index lowering effect all together, and hence is useful in the prevention or treatment of hyperlipidemia, arteriosclerosis, diabetes mellitus, hypertension, obesity, and the like.

  本发明提供了一种预防或治疗高脂血症的药物，其活性成分包括式 [1] 的杂环化合物或其药学上可接受的盐： R 1 -Het-D-E [1] 该预防或治疗剂具有降血甘油三酯作用、降低密度脂蛋白胆固醇作用、降血糖作用和降血胰岛素作用，或增加高密度脂蛋白胆固醇作用或降低动脉粥样硬化指数作用，因此可用于预防或治疗高脂血症、动脉硬化、糖尿病、高血压、肥胖症等。
• A CLASS OF BIFUNCTIONAL CHIMERIC HETEROCYCLIC COMPOUNDS FOR TARGETED DEGRADATION OF ANDROGEN RECEPTORS AND USE THEREOF
  申请人：Hinova Pharmaceuticals Inc.

  公开号：EP3957633A1

  公开（公告）日：2022-02-23

  The present invention relates to a class of bifunctional chimeric heterocyclic compounds for targeted degradation of androgen receptors and use thereof, and specifically provides a compound of formula (I), or an isotopic compound thereof, or an optical isomer thereof, or a tautomer thereof, or a pharmacologically acceptable salt thereof, or a prodrug thereof, or a solvate thereof, wherein ARB is an androgen receptor recognition/binding part, L is a link part, and U is a ubiquitin protease recognition/binding part; and the three parts are connected by means of chemical bonds. The compound can perform the targeted degradation on androgen receptors in prostate cancer cells, and suppress the proliferation of the prostate cancer cells, and also show good metabolic stability and pharmacokinetic properties. The compound has good application prospect in the preparation of targeted chimeras for protein degradation of androgen receptors and in the preparation of drugs for treating the related diseases regulated by the androgen receptors.

  本发明涉及一类用于靶向降解雄激素受体的双官能嵌合杂环化合物及其用途，具体提供了式(I)化合物，或其同位素化合物，或其光学异构体，或其同系物，或其药理学上可接受的盐，或其原药，或其溶媒，其中ARB为雄激素受体识别/结合部分，L为连接部分，U为泛素蛋白酶识别/结合部分；这三个部分通过化学键连接。该化合物能对前列腺癌细胞中的雄激素受体进行靶向降解，抑制前列腺癌细胞的增殖，并具有良好的代谢稳定性和药代动力学特性。该化合物在制备靶向降解雄激素受体蛋白的嵌合体和制备治疗受雄激素受体调控的相关疾病的药物方面具有良好的应用前景。