(3-acetyl-4-hydroxyphenyl)acetic acid methyl ester | 145042-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-acetyl-4-hydroxyphenyl)acetic acid methyl ester
• 英文别名: methyl 2-(3-acetyl-4-hydroxyphenyl)acetate；methyl (3-acetyl-4-hydroxyphenyl)acetate；Methyl 4-hydroxy-3-acetyl-phenylacetate
• CAS: 145042-91-7
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: MCUMSTSNBAXVFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-acetyl-4-hydroxyphenyl)acetic acid methyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 [4-Hydroxy-3-(3-phenyl-propionyl)-phenyl]-acetic acid methyl ester
  参考文献：
  名称：

  Development of potent and selective factor Xa inhibitors

  摘要：

  The development of potent and selective small molecule inhibitors of factor Xa is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00311-0
• 作为产物：
  描述：

  2-(4-乙酰氧基苯基)乙酸甲酯 在 三氯化铝 、 氯化亚砜 作用下， 生成 (3-acetyl-4-hydroxyphenyl)acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Phenylacetyl Derivatives Having Low Central Nervous System Permeability as Potent and Selective M2 Muscarinic Receptor Antagonists.

  摘要：

  一系列含有5,10-二氢-11H-二苯并[b,e][1,4]二氮杂卓-11-酮或5,11-二氢-6H-吡啶并[2,3-b][1,4]苯并二氮杂卓-6-酮骨架的苯乙酰基衍生物被制备并评估了它们与毒蕈碱受体在体外的结合亲和力以及对心动过缓、唾液分泌和震颤的体内拮抗作用。其中，化合物56和66对心脏中的M2毒蕈碱受体具有高亲和力（pKi分别为8.7和8.9），而对颌下腺中的M3毒蕈碱受体的亲和力较低。结构-活性关系（SAR）研究表明，56对M2受体的高选择性可能是由于酰胺羰基的定向。在体内研究中，56和66均能拮抗氧颤药引起的大鼠心动过缓，无论是静脉注射还是口服给药，且它们对夜间心动过缓的狗的心率增加效果是AF-DX 116的3倍左右。此外，它们对氧颤药引起的小鼠震颤几乎没有影响，无证据表明中枢转移。

  DOI：

  10.1248/cpb.46.53

文献信息

• 2-substituted quinolines, and their use in medicaments
  申请人：Bayer Aktiengesellschaft

  公开号：US05304563A1

  公开（公告）日：1994-04-19

  The title compounds are prepared either by reacting the corresponding halogenomethylquinolines with substituted phenols, optionally subsequently alkylating these or hydrolysing esters to acids, or by reacting phenyl-substituted quinolinecarboxylic acid derivatives with sulphonamides. The new phenyl-substituted quinolines are utilizable as active substances in medicaments, in particular as lipoxygenase inhibitors.

  这些标题化合物可以通过以下两种方法制备：将相应的卤代甲基喹啉与取代苯酚反应，随后可以选择性地烷基化或水解酯类化合物得到酸类化合物；或者将苯基取代的喹啉羧酸衍生物与磺胺酰胺反应。这些新的苯基取代喹啉可作为药物中的活性物质，特别是作为脂氧合酶抑制剂。
• KHMDS Enhanced SmI₂-Mediated Reformatsky Type α-Cyanation
  作者：Tobias Ankner、Maria Fridén-Saxin、Nils Pemberton、Tina Seifert、Morten Grøtli、Kristina Luthman、Göran Hilmersson

  DOI：10.1021/ol100424y

  日期：2010.5.21

  A novel combination of SmI2, KHMDS, and TsCN can be utilized to introduce a cyano group into structurally diverse and highly sensitive 2-alkyl-chroman-4-ones. Subsequent oxidation allows the formed 2-alkyl-3-cyanochromones to be isolated in yields ranging from 49 to 77%. In addition, alpha-bromoketones and esters were found to undergo equally effective alpha-cyanation.
• 2-(1-Adamantyl)-4-(thio)chromenone-6-carboxylic Acids:  Potent Reversible Inhibitors of Human Steroid Sulfatase
  作者：Amarylla Horvath、Peter Nussbaumer、Barbara Wolff、Andreas Billich

  DOI：10.1021/jm0407916

  日期：2004.8.1

  Steroid sulfatase (STS) is an attractive target for the potential therapy of a number of estrogen- and androgen-dependent disorders. Most potent STS inhibitors known so far act as irreversible enzyme blockers and feature an aryl sulfamate moiety; even minor modifications at the sulfamate group result in drastically decreased activity. On the basis of a recently reported subclass of highly potent STS inhibitors, i.e., chromenone sulfamates, we now extended the investigation of structure-activity relationships to hitherto unstudied sulfamate replacements. Thereby, we discovered 2-(1-adamantyl)-4-(thio)chromenone-6-carboxylic acids (5d and 5j) as potent, reversible inhibitors of STS. In a cell-free system using purified human STS, both new inhibitors show similar K-i values (0.50 muM and 0.53 muM, respectively). However, the thio analogue 5j is superior to 5d (IC50 = 0.18 muM versus 9.4 muM) in a cellular assay system using CHO cells overexpressing STS. Compound 5j is an example of a reversible STS inhibitor with potent activity toward the target enzyme in a cellular test system. Moreover, 5d,j are stable and have no estrogenic potential.
• US5304563A
  申请人：——

  公开号：US5304563A

  公开（公告）日：1994-04-19