3-(2,3-epoxypropoxy)xanthone | 37933-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(2,3-epoxypropoxy)xanthone
• 英文别名: 3-((oxiran-2-yl)methoxy)-9H-xanthen-9-one；3-(Oxiran-2-ylmethoxy)xanthen-9-one
• CAS: 37933-97-4
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: WOHZJXACIHPBMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3-(2,3-epoxypropoxy)xanthone 在 sodium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 以88%的产率得到3-(1,2-Dihydroxypropyl)oxy-9H-xanthen-9-one
  参考文献：
  名称：

  γ-吡喃酮化合物。5.黄嘌呤氧基丙醇胺和相关化合物的合成和抗血小板作用。

  摘要：

  合成了一系列简单的黄嘌呤氧基丙醇胺和相关化合物。3- [3-（环丙基氨基）丙氧基] -an吨酮对花生四烯酸酯诱导的聚集表现出与降冰片四醇四乙酸酯相同的有效抗血小板作用。3- [3-（环己基氨基）-2-羟基丙氧基]黄酮在胶原蛋白诱导的聚集方面显示出比降冰片四乙酸四乙酸酯更有效的抗血小板作用。合成化合物的氧丙醇胺或氧丙胺侧链的各种氨基调节抗血小板作用。

  DOI：

  10.1002/jps.2600830325
• 作为产物：
  描述：

  3-甲氧基氧杂蒽-9-酮 在 sodium hydroxide 、 氢碘酸 、 苯酚 作用下， 以 异丙醇 为溶剂， 反应 10.0h， 生成 3-(2,3-epoxypropoxy)xanthone
  参考文献：
  名称：

  γ-吡喃酮化合物。IV：单和双氧合的氧杂蒽和氧杂氧丙醇胺的合成和抗血小板作用。

  摘要：

  由二苯甲酮前体合成黄原醇，单和双氧合的氧杂蒽，以及1,3-，2,3-，3,4-，3,5-，1,6-，2,6-和3,6-二氧合的氧杂蒽由Friedel-Crafts酰化，然后进行碱催化的环化反应以消除甲醇。3-羟-吨酮，黄酮醇，2,3-二羟x吨酮二乙酸盐和3,4-二羟di吨酮及其二乙酸盐对花生四烯酸和胶原诱导的聚集表现出有效的抗血小板作用。3,5-二羟基黄酮及其双乙酸盐，1,6-二甲氧基黄酮和3,6-二羟基黄酮及其二乙酸盐对花生四烯酸诱导的聚集表现出有效的抗血小板作用。

  DOI：

  10.1002/jps.2600820103

文献信息

• Preliminary evaluation of pharmacological properties of some xanthone derivatives
  作者：Henryk Marona、Natalia Szkaradek、Anna Rapacz、Barbara Filipek、Małgorzata Dybała、Agata Siwek、Marek Cegła、Edward Szneler

  DOI：10.1016/j.bmc.2008.12.031

  日期：2009.2

  A series of xanthone derivatives were synthesized and examined for electrocardiographic, antiarrhythmic, hypotensive and anticonvulsant activities as well as for α1- and β1-adrenergic binding affinities. Among the investigated compounds, some of them exhibited significant antiarrhythmic and/or hypotensive activity. The data obtained via receptor binding assay are in agreement with pharmacological results

  一系列呫吨酮衍生物的合成和检查心电图，抗心律不齐，降血压和抗惊厥活性，以及用于α 1 -和β 1 -肾上腺素能结合亲和力。在所研究的化合物中，其中一些表现出明显的抗心律不齐和/或降压活性。通过受体结合测定获得的数据与药理学结果一致，并且可以解释新合成结构的抗心律不齐和/或降压活性。
• Design, synthesis and cardiovascular evaluation of some aminoisopropanoloxy derivatives of xanthone
  作者：M. Kubacka、N. Szkaradek、S. Mogilski、K. Pańczyk、A. Siwek、A. Gryboś、B. Filipek、P. Żmudzki、H. Marona、A.M. Waszkielewicz

  DOI：10.1016/j.bmc.2018.04.038

  日期：2018.7

  entry blocking activity. The title compounds showed hypotensive and antiarrhythmic properties due to their adrenoceptor blocking effect. Moreover, they did not affect QRS and QT intervals, and they did not have proarrhythmic potential at tested doses. In addition they exerted anti-aggregation effect. The results of this study suggest that new compounds with multidirectional activity in cardiovascular

  已经合成了一系列的蒽酮的氨基异丙醇氧基衍生物，并评估了它们与心血管系统有关的药理特性。在离体器官中进行放射性配体结合和功能研究表明，标题化合物对α1-（化合物2和8），β-（化合物1、3、4、7），α1/β-（化合物5和6）具有很高的亲和力和拮抗力）肾上腺素受体。此外，维拉帕米的结构类似物化合物7具有阻止钙进入的活性。标题化合物由于其肾上腺素受体阻断作用而显示出降压和抗心律不齐的特性。此外，它们没有影响QRS和QT间隔，并且在测试剂量下没有心律失常的可能。另外，它们发挥了抗聚集作用。
• Synthesis and pharmacological activity of a series of novel xanthone
  申请人：National Science Council

  公开号：US05495005A1

  公开（公告）日：1996-02-27

  A compound, and salts thereof, represented by either formula I or formula II below: (1) Formula I: ##STR1## wherein substituents R.sub.1 -R.sub.7 can be, independently, hydrogen, hydroxy group, C.sub.1-6 alkyl(oxy) group, acetyl ester, or C.sub.1-12 alkyl propanolamine; at least three but no more than four of the substituents are alkyl(oxy) group, hydroxyl group or acetyl ester; no more than one of the substituents can be C.sub.1-12 alkyl propanolamines; R.sub.1, R.sub.3, R.sub.7 cnnnot all be hydroxy groups at the same time; and R.sub.6 is either an hydroxy group or an oxygen-containing glucose. (2) Formula II: ##STR2## wherein substituents R.sub.1 -R.sub.9 can be, indenpendently, hydrogen, hydroxy group and C.sub.1-6 alkyl(oxy) group; and no more then four of the substituents can be methoxy group, hydroxy group, or acetyl ester. These compounds were tested to be capable of inhibiting platelet aggregation, atrioventricular conduction, and calcium influx in myocardiac cells.

  以下是公式I或公式II所代表的化合物及其盐：（1）公式I：其中取代基R.sub.1 -R.sub.7可以独立地是氢、羟基、C.sub.1-6烷基（氧）基、乙酰酯或C.sub.1-12烷基丙醇胺；至少三个但不超过四个取代基是烷基（氧）基、羟基或乙酰酯；不超过一个取代基可以是C.sub.1-12烷基丙醇胺；R.sub.1、R.sub.3、R.sub.7不能同时是羟基；R.sub.6是羟基或含氧葡萄糖。 （2）公式II：其中取代基R.sub.1 -R.sub.9可以独立地是氢、羟基和C.sub.1-6烷基（氧）基；不超过四个取代基可以是甲氧基、羟基或乙酰酯。 这些化合物经测试表明能够抑制血小板聚集、房室传导和心肌细胞内的钙通道。
• Marona; Pekala; Filipek, Pharmazie, 2001, vol. 56, # 7, p. 567 - 572
  作者：Marona、Pekala、Filipek、Maciag、Szneler

  DOI：——

  日期：——
• Cardiovascular activity of the chiral xanthone derivatives
  作者：Natalia Szkaradek、Anna Rapacz、Karolina Pytka、Barbara Filipek、Dorota Żelaszczyk、Przemysław Szafrański、Karolina Słoczyńska、Henryk Marona

  DOI：10.1016/j.bmc.2015.09.005

  日期：2015.10

  A series of 6 derivatives of xanthone were synthesized and evaluated for cardiovascular activity. The following pharmacological experiments were conducted: the binding affinity for adrenoceptors, the influence on the normal electrocardiogram, the effect on the arterial blood pressure, the effect on blood pressor response and prophylactic antiarrhythmic activity in adrenaline induced model of arrhythmia (rats, iv). Two compounds revealed nanomolar affinity for alpha(1)-adrenoceptor which was correlated with the strongest cardiovascular (antiarrhythmic and hypotensive) activity in animals' models. They were enantiomers of previously described (R, S)-4-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propoxy)- 9H-xanthen-9-one hydrochloride and revealed similar antiarrhythmic potential in adrenaline induced model of arrhythmia in rats after intravenous injection (ED50 = 0.53 mg/kg and 0.81 mg/kg, respectively). These values were lower than values obtained for reference drug urapidil. These compounds were more active in this experiment than urapidil (ED50 = 1.26 mg/kg). The compound 5 administered iv at doses of 0.62-2.5 mg/kg at the peak of arrhythmia prevented and/or reduced the number of premature ventricular beats in a statistically significant manner. The ED50 value was 1.20 mg/kg. The S-enantiomer (6) given at the same doses did not show therapeutic antiarrhythmic activity in this model.These compounds significantly decreased the systolic and diastolic blood pressure throughout the whole observation period in anesthetized, normotensive rats. The studied enantiomers showed higher toxicity than urapidil, but imperceptibly higher that another cardiovascular drugs, that is, carvedilol or propranolol. They were also evaluated for mutagenic potential in the Ames (Salmonella) test. It was found that at the concentrations tested the compounds were non mutagenic when compared to solvent control.Results were quite promising and suggested that in the group of xanthone derivatives new potential antiarrhythmics and hypotensives might be found. (c) 2015 Elsevier Ltd. All rights reserved.