7-<(1,2-dihydroxypropyl)oxy>coumarin | 22919-21-7

• 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: 7-<(1,2-dihydroxypropyl)oxy>coumarin
• 英文别名: 7-(2,3-dihydroxypropoxy)-2H-1-benzopyran-2-one；7-(2,3-dihydroxypropoxy)-2H-chromen-2-one；1-O-(7-coumarinyl) glycerol；3-O-(7-coumarinyl) glycerol；7-(1-O-glyceryloxy)coumarin；1-O-(7-coumarinyl)glycerol；2H-1-Benzopyran-2-one, 7-(2,3-dihydroxypropoxy)-；7-(2,3-dihydroxypropoxy)chromen-2-one
• CAS: 22919-21-7
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: LDRUKBXKOFTVNA-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  501.4±50.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：

  7-<(1,2-dihydroxypropyl)oxy>coumarin 在 sodium periodate 、 正丁基锂 、 二异丙胺 、 N,N'-二环己基碳二亚胺 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 66.0h， 生成 7-[[(2E)-3-(4,5-二氢-5,5-二甲基-4-氧代-2-呋喃基)-2-丁烯-1-基]氧基]-2H-1-苯并吡喃-2-酮
  参考文献：
  名称：

  Synthesis and configurational assignment of geiparvarin: a novel antitumor agent

  摘要：

  DOI：

  10.1021/jo00316a018
• 作为产物：
  描述：

  7-羟基香豆素 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 7-<(1,2-dihydroxypropyl)oxy>coumarin
  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

• Non-nucleosidic coumarin derivatives as polynucleotide-crosslinking agents
  申请人：Naxcor, Inc.

  公开号：US06800768B1

  公开（公告）日：2004-10-05

  Novel coumarin derivatives comprising a coumarin moiety linked to a non-nucleosidic backbone moiety are disclosed. The resulting molecules are typically used as photoactivate crosslinking groups when incorporated into polynucleotides as replacements for one or more of the complementary nucleoside bases present in probes used in procedures involving nucleic acid hybridization reactions.

  揭示了一种包括香豆素基团连接到非核苷骨架基团的新型香豆素衍生物。通常将得到的分子用作光活化交联基团，当它们被纳入多核苷酸中作为替代品时，可以替代探针中存在的一个或多个互补核苷酸碱基，用于涉及核酸杂交反应的程序中。
• Artificial aldolases from peptide dendrimer combinatorial libraries
  作者：Jacob Kofoed、Tamis Darbre、Jean-Louis Reymond

  DOI：10.1039/b607342e

  日期：——

  Peptide dendrimers were investigated as synthetic models for aldolase enzymes. Combinatorial libraries were prepared with aldolase active residues such as lysine and proline placed at the dendrimer core or near the surface. On-bead selection for aldolase activity was carried out using the dye-labelled 1,3-diketone 1a, suitable for covalent trapping of enamine-reactive side-chains, and the fluorogenic

  研究了肽树状聚合物作为醛缩酶的合成模型。用醛缩酶活性残基例如赖氨酸和脯氨酸置于树状聚合物核心或表面附近制备组合文库。使用适合于共价捕获烯胺反应性侧链的染料标记的1,3-二酮1a和荧光烯醇化探针6，对醛缩酶活性进行珠上选择。醛缩酶树状聚合物催化丙酮的醛醇缩合反应，二羟基丙酮和环己酮与硝基苯甲醛。与酶一样，树枝状聚合物在水性介质中显示出强醛缩酶活性，但在有机溶剂中也具有活性。树枝状聚合物催化的醛醇缩合反应在1小时内在25摄氏度下用1 mol％的催化剂在3小时内达到了完全转化，并给出了醛基产物的ee高达65％。
• 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
• Nucleic acid sequence detection employing probes comprising non-nucleosidic coumarin derivatives as polynucleotide-crosslinking agents
  申请人：Naxcor

  公开号：US06495676B1

  公开（公告）日：2002-12-17

  Methods and compositions are provided for detecting nucleic acid sequences. Probes comprising a crosslinking agent are combined with a sample which may comprise a target sequence which is complementary to the probe. Hybridization is allowed to occur between complementary sequences. The crosslinking agent is activated. Covalent bonds are formed between the probe and the target sequence if they are hybridized to one another. The crosslinked nucleic acids can then be detected to indicate the presence of the target sequence. Also provided are kits comprising reagents.

  提供了检测核酸序列的方法和组合物。将含有交联剂的探针与样品结合，该样品可能包含与探针互补的目标序列。允许互补序列之间的杂交发生。激活交联剂。如果探针和目标序列相互杂交，则形成共价键。然后可以检测交联的核酸以指示目标序列的存在。还提供包含试剂的试剂盒。
• Double-stranded conformational polymorphism analysis
  申请人：Naxcor

  公开号：US20010012616A1

  公开（公告）日：2001-08-09

  Double-stranded conformational polymorphism analysis is performed by combining a probe comprising a cross-linking agent and optionally a label with a sample having a target sequence, which may be complementary or have one or a few mismatches with respect to the probe sequence. After sufficient time for hybridization under mild or lesser stringency conditions, hybridized pairs are irradiated to induce cross-link formation by the cross-linking agent. The sample is then analyzed by denaturing gel electrophoresis where the rate of migration depends upon the degree of complementarity between the probe and the target. For corroboration, in a second experiment, the probe may be combined with the sample under high stringency conditions, where it is found that the formation of cross-linked probe/target is substantially lower for pairs having mismatches than for fully matched pairs. After cross-linking, the sample may be separated by gel electrophoresis, and the amount of cross-linked nucleic acid determined.

  双链构象多态性分析的方法是将含有交联剂和标记的探针与具有目标序列的样品结合，目标序列可能与探针序列互补，也可能有一个或几个错配。在温和或较宽松的条件下，经过足够时间的杂交后，对杂交对进行辐照，以诱导交联剂形成交联。然后用变性凝胶电泳分析样本，迁移率取决于探针和目标物之间的互补程度。为了证实这一点，在第二次实验中，可在高严格条件下将探针与样品结合，结果发现，与完全匹配的探针对相比，具有错配的探针对/目标对形成交联的几率要低得多。交联后，可通过凝胶电泳分离样品，并测定交联核酸的量。