methyl (4'-acetyl-3'-hydroxy-2'-propylphenoxy)acetate | 88420-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4'-acetyl-3'-hydroxy-2'-propylphenoxy)acetate
• 英文别名: (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid methyl ester；Methyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate；methyl 2-(4-acetyl-3-hydroxy-2-propylphenoxy)acetate
• CAS: 88420-26-2
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: FZFJBRPFCPPCBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  401.8±45.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4'-acetyl-3'-hydroxy-2'-propylphenoxy)acetate 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以39%的产率得到(4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid
  参考文献：
  名称：

  Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives

  摘要：

  A series of derivatives of 2,4-dihydroxy-3-propylacetophenone(1) were prepared and examined for their ability to block leukotriene D4 (LTD4) induced contraction of guinea pig ileum. Straight-chain carboxylic acids where the carboxyl group was separated from the acetophenone moiety by varying numbers of methylenes were evaluated, and maximum activity was obtained with the pentamethylene acid (6). Examination of ring substitution showed that the 2-propyl-3-hydroxy-4-acetyl substitution pattern was required for maximum LTD4 antagonist activity. Additional chain terminal groups were examined, and the acidic 5-tetrazolyl group separated from the acetophenone moiety by four to seven methylenes (26, 23, 27, 28) gave excellent in vitro and in vivo activities. Compound 26 (LY171883) had the best balance of in vitro and in vivo activity. It lacked bronchospastic activity at the doses administered and has been chosen for clinical evaluation.

  DOI：

  10.1021/jm00387a018
• 作为产物：
  描述：

  2,4-二羟基-3-丙基苯乙酮 、 溴乙酸甲酯 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以47%的产率得到methyl (4'-acetyl-3'-hydroxy-2'-propylphenoxy)acetate
  参考文献：
  名称：

  Leukotriene receptor antagonists. 1. Synthesis and structure-activity relationships of alkoxyacetophenone derivatives

  摘要：

  A series of derivatives of 2,4-dihydroxy-3-propylacetophenone(1) were prepared and examined for their ability to block leukotriene D4 (LTD4) induced contraction of guinea pig ileum. Straight-chain carboxylic acids where the carboxyl group was separated from the acetophenone moiety by varying numbers of methylenes were evaluated, and maximum activity was obtained with the pentamethylene acid (6). Examination of ring substitution showed that the 2-propyl-3-hydroxy-4-acetyl substitution pattern was required for maximum LTD4 antagonist activity. Additional chain terminal groups were examined, and the acidic 5-tetrazolyl group separated from the acetophenone moiety by four to seven methylenes (26, 23, 27, 28) gave excellent in vitro and in vivo activities. Compound 26 (LY171883) had the best balance of in vitro and in vivo activity. It lacked bronchospastic activity at the doses administered and has been chosen for clinical evaluation.

  DOI：

  10.1021/jm00387a018

文献信息

• Phenoxycarboxylic acids
  申请人：Hoffmann-La Roche Inc.

  公开号：US04507498A1

  公开（公告）日：1985-03-26

  Phenoxycarboxylic acids of the formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, Z and n are as hereinafter set forth, are as described. The compounds of formula I are antagonists of slow reacting substance of anaphylaxis (SRS-A), which renders them useful as agents for the treatment of allergic conditions.

  公式为##STR1##的苯氧羧酸，其中R、R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5、Z和n如下所述。公式I的化合物是过敏反应缓慢物质（SRS-A）的拮抗剂，这使它们可用作治疗过敏症状的药物。
• Discovery of a New Chalcone-Trimethoxycinnamide Hybrid with Antimitotic Effect: Design, Synthesis, and Structure—Activity Relationship Studies
  作者：Joana Moreira、Patrícia M. A. Silva、Matilde Barros、Lucília Saraiva、Madalena Pinto、Hassan Bousbaa、Honorina Cidade

  DOI：10.3390/ph16060879

  日期：——

  In this work, the design and synthesis of a new chalcone-trimethoxycinnamide hybrid (7) based on the combination of subunits of two promising antiproliferative compounds (CM-M345 (1) and BP-M345 (2)), previously obtained by our research group, are reported. In order to expand the structure–activity relationship (SAR) knowledge, a new series of 7-analogues was also designed and synthetized. All the

  在这项工作中，基于我们先前研究获得的两种有前景的抗增殖化合物（CM-M345 (1) 和 BP-M345 (2)）的亚基组合，设计和合成了一种新的查耳酮-三甲氧基肉桂酰胺杂化物 (7)组，进行报道。为了扩展构效关系（SAR）知识，还设计并合成了一系列新的7-类似物。评估了所有化合物对黑色素瘤 (A375-C5)、乳腺癌 (MCF-7) 和结直肠癌 (HCT116) 细胞系以及非肿瘤 HPAEpiC 细胞的抗肿瘤活性。三种新合成的化合物（6、7和13）表现出有效的抗增殖活性，主要针对结直肠肿瘤细胞（GI50 = 2.66–3.26 μM），显示出杂种7对肿瘤细胞的选择性。我们进行了分子机制研究，以评估化合物对 p53 通路的潜在干扰，即 HCT116 细胞中 p53-MDM2 相互作用和有丝分裂。化合物的抗增殖活性被证明不依赖于p53。化合物 7 通过诱导结直肠肿瘤细胞有丝分裂停滞以及随后的细胞死亡而成为抗有丝分裂剂。
• MARSHALL W. S.; GOODSON T.; CULLINAN G. J.; SWANSON-BEAN D.; HAISCH K. D.+, J. MED. CHEM., 30,(1987) N 4, 682-689
  作者：MARSHALL W. S.、 GOODSON T.、 CULLINAN G. J.、 SWANSON-BEAN D.、 HAISCH K. D.+

  DOI：——

  日期：——
• US4507498A
  申请人：——

  公开号：US4507498A

  公开（公告）日：1985-03-26
• US4782176A
  申请人：——

  公开号：US4782176A

  公开（公告）日：1988-11-01