4-(环氧乙烷甲氧基)-苯丙酸甲酯 | 81147-94-6

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(环氧乙烷甲氧基)-苯丙酸甲酯
• 英文名称: methyl 3-[4-(oxiran-2-ylmethoxy)phenyl]propanoate
• 英文别名: Benzenepropanoic acid, 4-(oxiranylmethoxy)-, methyl ester
• CAS: 81147-94-6
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: BDCUIFGTTIEBLT-UHFFFAOYSA-N

物化性质

• 沸点：
  156 °C(Press: 0.4 Torr)
• 密度：
  1.163±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(环氧乙烷甲氧基)-苯丙酸甲酯 在 三丁基氧化锡 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.25h， 生成 艾司洛尔酸
  参考文献：
  名称：

  Hitting a Soft Drug with a Hard Nucleophile: Preparation of Esmolol's Metabolite by Treatment with Bis(tributyltin) Oxide

  摘要：

  A facile method for the production of esmolol's metabolite in high purity is described. Bis(tributyltin) oxide is used to disrupt esmolol's ester linkage, and hydrolysis is completed by addition of water, which also allows the inorganic side products to be conveniently extracted into ether. Evaporation of the aqueous phase and trituration with ethyl acetate provides the carboxylic acid-amine internal salt as a white, free-flowing powder.

  DOI：

  10.1080/00397911.2010.530375
• 作为产物：
  描述：

  对羟基苯丙酸 在 3 A molecular sieve 、 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 92.0h， 生成 4-(环氧乙烷甲氧基)-苯丙酸甲酯
  参考文献：
  名称：

  超短效β-肾上腺素受体阻断剂。2.在芳基官能团上含有酯的（芳氧基）丙醇胺。

  摘要：

  通过将酯官能团结合到某些（芳氧基）丙醇胺系统的芳基部分中，已经制备了几种短效β-肾上腺素能受体阻断剂。特别是，发现3- [4- [2-羟基-3-（异丙基氨基）丙氧基]苯基]丙酸甲酯盐酸盐（ASL-8052）是一种中度有效的心脏选择性化合物，当在以下条件下测定时具有短的作用时间体内犬模型。

  DOI：

  10.1021/jm00354a003

文献信息

• Pd(II)-Catalyzed Intermolecular Arylation of Unactivated C(sp³)–H Bonds with Aryl Bromides Enabled by 8-Aminoquinoline Auxiliary
  作者：Yu Wei、Huarong Tang、Xuefeng Cong、Bin Rao、Chao Wu、Xiaoming Zeng

  DOI：10.1021/ol500745t

  日期：2014.4.18

  less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp3)–H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp3)–H activation-led

  描述了在Pd（II）催化的未活化C（sp 3）-H键的分子间芳基化中使用容易获得的，反应性较低的芳基溴化物作为芳基化试剂的示例。至关重要的8-氨基喹啉基导向基团和K 2 CO 3碱促进了该反应，从而使芳基骨架可以在羧酰胺的β-位上进行区域特异性安装。通过DFT计算进行的机理研究揭示了C（sp 3）–H活化为主导的途径，该途径的特征是氧化加成为最高能量跃迁状态。
• Esters of thiadiazole oxypropanolaine derivatives and pharmaceutical uses
  申请人：American Hospital Supply Corporation

  公开号：US04623652A1

  公开（公告）日：1986-11-18

  Novel compounds of the general formula ##STR1## wherein R.sub.1 is lower alkyl, lower cycloalkyl, lower alkenyl, lower alkynyl, lower alkyl carboxymethyl, aryl carboxymethyl, aryl, or aralkyl; A is a direct bond, lower alkylene, or lower alkenylene; x is 1 or 2, provided that when x is greater than 1, different occurrences of the ##STR2## group may be the same or different; Ar is heterocyclic, unsubstituted aromatic or aromatic substituted with lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, halogen, acetamido, amino, nitro, lower alkylamino, hydroxy, lower hydroxyalkyl or cyano; W is alkylene containing from 1 to about 10 carbon atoms; and B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.2 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5 to 7 membered heterocyclic group; and the pharmaceutically acceptable salts thereof.

  通用公式为##STR1##的新型化合物，其中R.sub.1是较低的烷基、较低的环烷基、较低的烯基、较低的炔基、较低的烷基羧甲基、芳基羧甲基、芳基或芳基烷基；A是直链键、较低的烷基烯烃或较低的烯烃基；x为1或2，但当x大于1时，##STR2##基的不同发生位置可能相同或不同；Ar为杂环、未取代的芳香族或芳香族取代的较低烷基、较低烯基、较低炔基、较低烷氧基、卤素、乙酰胺基、氨基、硝基、较低烷基氨基、羟基、较低羟基烷基或氰基；W为含有1至约10个碳原子的烷基；B为--NR.sub.2 COR.sub.3、--NR.sub.2 CONR.sub.3 R.sub.4、--NR.sub.2 SO.sub.2 R.sub.3、--NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4或--NR.sub.2 COOR.sub.5，其中R.sub.2、R.sub.3、R.sub.4和R.sub.5可能相同也可能不同，可以是氢、烷基、烷氧基烷基、烷氧基芳基、环烷基、烯基、炔基、芳基、杂环芳基或芳基烷基，但当B为--NR.sub.2 SO.sub.2 R.sub.3或--NR.sub.2 COOR.sub.5时，R.sub.3和R.sub.5不是氢，或者R.sub.3和R.sub.4可以与N一起形成5到7个成员的杂环基团；及其药用盐。
• Synthesis and Structure-Activity Relationship of 4-Substituted Benzoic Acids and their Inhibitory Effect on the Biosynthesis of Fatty Acids and Sterols
  作者：Tomoyasu Ohno、Kazuo Ogawa、Shingo Yano、Masakazu Fukushima、Norihiko Suzuki、Tetsuji Asao

  DOI：10.1002/ardp.200400920

  日期：2005.4

  The synthesis of 4‐[3‐(substituted phenyl)‐2‐oxo‐5‐oxazolidinyl]methoxybenzoic acids and their inhibitory effects on the biosynthesis of fatty acids and sterols is described. IC50 values in vitro were 10−6 and 10−5 M, respectively. Though the in vitro inhibitory activity of all these compounds toward sterol biosynthesis was inferior to that of pravastatin, several compounds had a stronger reducing

  描述了 4-[3-(取代苯基)-2-氧代-5-恶唑烷基]甲氧基苯甲酸的合成及其对脂肪酸和甾醇生物合成的抑制作用。体外IC50值分别为10-6和10-5M。尽管所有这些化合物对甾醇生物合成的体外抑制活性不如普伐他汀，但有几种化合物在 Sprague-Dawley (SD) 大鼠中对胆固醇 (TC) 和甘油三酯 (TG) 的降低作用比普伐他汀更强和苯扎贝特。强效化合物以高浓度存在于大鼠肝脏中。制备了有效外消旋化合物（4-[3-（4-溴-2-氟苯基）-2-氧代-5-恶唑烷基]甲氧基苯甲酸）的对映体，并在体内和体外检测了它们的活性。在体内，每种对映异构体都比外消旋化合物具有更高的活性。
• Development of a Highly Cardioselective Ultra Short-Acting .BETA.-Blocker, ONO-1101.
  作者：Sadahiko IGUCHI、Hiroyuki IWAMURA、Minoru NISHIZAKI、Akio HAYASHI、Kazuhiko SENOKUCHI、Kaoru KOBAYASHI、Katsuhito SAKAKI、Katsutoshi HACHIYA、Yumiko ICHIOKA、Masanori KAWAMURA

  DOI：10.1248/cpb.40.1462

  日期：——

  A novel, highly cardioselective ultra short-acting β-blocker, ONO-1101, has been developed for application in the emergency treatment of tachycardia and better control of heart rate in surgery. This agent is approximately nine times more potent in β-blocking activity in vivo and eight times more cardioselective in vitro than esmolol. This β-blocking drug has a short duration of activity, enabling rapid recovery after cessation of administration if side effects occur. It can be used safely in patients suffering from acute heart disease and represents a major therapeutic advance in the treatment of heart disease.

  一种新型、高度心脏选择性超短效β受体阻滞剂ONO-1101已研发成功，可用于心动过速的紧急治疗和手术中更好地控制心率。该药物在体内的β受体阻断活性比艾司洛尔强约9倍，在体外的心脏选择性比艾司洛尔强8倍。这种β受体阻断药物的作用时间短，如果出现副作用，停药后即可迅速恢复。它可安全用于急性心脏病患者，是心脏病治疗领域的一大进步。
• Nonpeptidic Propargylamines as Inhibitors of Lysine Specific Demethylase 1 (LSD1) with Cellular Activity
  作者：Martin L. Schmitt、Alexander-Thomas Hauser、Luca Carlino、Martin Pippel、Johannes Schulz-Fincke、Eric Metzger、Dominica Willmann、Teresa Yiu、Michelle Barton、Roland Schüle、Wolfgang Sippl、Manfred Jung

  DOI：10.1021/jm400792m

  日期：2013.9.26

  Lysine demethylases play an important role in epigenetic regulation and thus in the development of diseases like cancer or neurodegenerative disorders. As the lysine specific demethylase 1 (LSD1/KDM1) has been strongly connected to androgen and estrogen dependent gene expression, it serves as a promising target for the therapy of hormone dependent cancer. Here, we report on the discovery of new small

  赖氨酸脱甲基酶在表观遗传调控中发挥重要作用，因此在癌症或神经退行性疾病等疾病的发展中起着重要作用。由于赖氨酸特异性脱甲基酶 1 (LSD1/KDM1) 与雄激素和雌激素依赖性基因表达密切相关，因此它是治疗激素依赖性癌症的有希望的靶点。在这里，我们报告了新的 LSD1 小分子抑制剂的发现，该抑制剂含有炔丙胺弹头，从含有赖氨酸的底物类似物开始。在这些底物模拟抑制剂的基础上，我们能够通过基于相似性的虚拟筛选和随后的合成优化相结合来提高效力，从而产生更多类似药物的 LSD1 抑制剂，从而导致乳腺癌细胞中的组蛋白高甲基化。