4-(2,3-Dihydroxy-propoxy)-chromen-2-one | 178321-46-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(2,3-Dihydroxy-propoxy)-chromen-2-one
• 英文别名: 4-(2,3-Dihydroxypropoxy)chromen-2-one
• CAS: 178321-46-5
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: JEXLYSRZWDYTIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,3-Dihydroxy-propoxy)-chromen-2-one 在 sodium periodate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以60%的产率得到2-(2-oxo-2H-1-benzopyran-4-yloxy)acetaldehyde
  参考文献：
  名称：

  香豆素α-亚甲基-γ-丁内酯的合成，抗增殖和血管松弛评估。

  摘要：

  合成了某些香豆素α-亚甲基-γ-丁内酯，并评估了其抗增殖和血管舒张活性。这些化合物是通过羟基香豆素2a-f的烷基化，氧化和Reformatsky型缩合反应合成的。这项研究的结果如下：（1）对于血管松弛活性，香豆素-7-基α-亚甲基-γ-丁内酯6d对氯化钾引起的猪冠状动脉收缩的IC50值为9.4 microM，活性更高。血管舒张剂比其香豆素-4-基对应物6a和它的γ-甲基同源物1。在香豆素-7-基部分的C-4处取代的甲基降低了血管舒张作用（6d vs 6e），而3,4,8 -三甲基衍生物6f是无活性的。（2）香豆素-4-基α-亚甲基-γ-丁内酯6a具有抗增殖活性，它们对MCF7，NCI-H460和SF-268的生长表现出最强的抗增殖活性，IC50值分别为6.97、14.68和8.36 microM，比其香豆素7-基对应物6d和6具有更强的细胞毒性。 ，7-二甲基衍生物6b。对于香豆素-7-基

  DOI：

  10.1016/j.bmc.2005.06.013
• 作为产物：
  描述：

  羟甲香豆素 在 四氧化锇 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 23.0h， 生成 4-(2,3-Dihydroxy-propoxy)-chromen-2-one
  参考文献：
  名称：

  Enzyme Activity Fingerprinting with Substrate Cocktails

  摘要：

  In the postgenomic era, emphasis is shifting from protein identification to protein functional analysis. Enzyme function can be characterized by measuring activity across series of substrates, which generates an activity profile or fingerprint. Activity fingerprinting is particularly useful to differentiate closely related enzymes. Previously reported fingerprinting methods use series of parallel measurements, which are complex and difficult to reproduce. Here we report a new method for fingerprinting enzyme activities based on using mixtures of substrates, or substrate cocktails, in a single reaction that is then analyzed by HPLC. The fingerprints produced are highly reproducible and allow functional differentiation and classification of closely related enzymes, as demonstrated for a series of lipases and esterases. The method is practical, general, and flexible in terms of reaction conditions and can be adapted to any reaction type.

  DOI：

  10.1021/ja0478330

文献信息

• Synthesis of Coumarin Derivatives as Inhibitors of Platelet Aggregation
  作者：Yeh-Long Chen、Tai-Chi Wang、Kuan-Han Lee、Cherng-Chyi Tzeng、Ya-Ling Chang、Che-Ming Teng

  DOI：10.1002/hlca.19960790308

  日期：1996.5.8

  In a search for the inhibitors of platelet aggregation, certain coumarin derivatives were synthesized and evaluated for antiplatelet activity against thrombin(Thr)-, arachidonic acid(AA)-, collagen(Col)-, and platelet-activating-factor(PAF)-induced aggregation in washed rabbit platelets. These compounds were synthesized from 4-hydroxycoumarin (1) or naphthalen-1-ol via alkylation and Reformatsky-type

  在寻找血小板聚集抑制剂时，合成了某些香豆素衍生物并评估了其对凝血酶（Thr）-，花生四烯酸（AA）-，胶原蛋白（Col）-和血小板活化因子（PAF）-的抗血小板活性。在洗涤的兔血小板中诱导聚集。这些化合物是由4-羟基香豆素（1）或萘-1-醇经烷基化和Reformatsky型缩合反应合成的（图1-3）。其中，显示了4-[（（2,3,4,5-四氢-4-亚甲基-5-氧代-2-苯基呋喃-2-基）甲氧基] -2 H -1-苯并吡喃-2-酮（6b）IC 50对AA和PAF诱导的聚集产生有效的抗血小板作用值分别为8.21和103.67m̈M（见表1和2）。通过在内酯环的2-苯基上引入适当的取代基，可以进一步提高6b对PAF诱导的聚集的抗血小板效力。
• Enzyme Activity Fingerprinting with Substrate Cocktails
  作者：Jean-Philippe Goddard、Jean-Louis Reymond

  DOI：10.1021/ja0478330

  日期：2004.9.1

  In the postgenomic era, emphasis is shifting from protein identification to protein functional analysis. Enzyme function can be characterized by measuring activity across series of substrates, which generates an activity profile or fingerprint. Activity fingerprinting is particularly useful to differentiate closely related enzymes. Previously reported fingerprinting methods use series of parallel measurements, which are complex and difficult to reproduce. Here we report a new method for fingerprinting enzyme activities based on using mixtures of substrates, or substrate cocktails, in a single reaction that is then analyzed by HPLC. The fingerprints produced are highly reproducible and allow functional differentiation and classification of closely related enzymes, as demonstrated for a series of lipases and esterases. The method is practical, general, and flexible in terms of reaction conditions and can be adapted to any reaction type.
• Synthesis, antiproliferative, and vasorelaxing evaluations of coumarin α-methylene-γ-butyrolactones
  作者：Yeh-Long Chen、Chih-Ming Lu、Shoiw-Ju Lee、Daih-Huang Kuo、I-Li Chen、Tai-Chi Wang、Cherng-Chyi Tzeng

  DOI：10.1016/j.bmc.2005.06.013

  日期：2005.10

  microM against pig coronary arterial contraction induced by KCl, is a more active vasorelaxant than its coumarin-4-yl counterpart 6a and its gamma-methyl congener 1. A methyl group substituted at C-4 of the coumarin-7-yl moiety reduced the vasorelaxing effect (6d vs 6e) while the 3,4,8-trimethyl derivative 6f was inactive. (2) For the antiproliferative activity, coumarin-4-yl alpha-methylene-gamma-butyrolactone

  合成了某些香豆素α-亚甲基-γ-丁内酯，并评估了其抗增殖和血管舒张活性。这些化合物是通过羟基香豆素2a-f的烷基化，氧化和Reformatsky型缩合反应合成的。这项研究的结果如下：（1）对于血管松弛活性，香豆素-7-基α-亚甲基-γ-丁内酯6d对氯化钾引起的猪冠状动脉收缩的IC50值为9.4 microM，活性更高。血管舒张剂比其香豆素-4-基对应物6a和它的γ-甲基同源物1。在香豆素-7-基部分的C-4处取代的甲基降低了血管舒张作用（6d vs 6e），而3,4,8 -三甲基衍生物6f是无活性的。（2）香豆素-4-基α-亚甲基-γ-丁内酯6a具有抗增殖活性，它们对MCF7，NCI-H460和SF-268的生长表现出最强的抗增殖活性，IC50值分别为6.97、14.68和8.36 microM，比其香豆素7-基对应物6d和6具有更强的细胞毒性。 ，7-二甲基衍生物6b。对于香豆素-7-基