7-(3-hydroxypropoxy)-4-methyl-2H-chromen-2-one

• 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-(3-hydroxypropoxy)-4-methyl-2H-chromen-2-one
• 英文别名: 7-(3-Hydroxypropoxy)-4-methylchromen-2-one
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: LTHOLVRVWAIRDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(3-hydroxypropoxy)-4-methyl-2H-chromen-2-one 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.08h， 生成 7-[3-[2-Methoxy-5-(trifluoromethyl)pyridin-1-ium-1-yl]propoxy]-4-methylchromen-2-one;trifluoromethanesulfonate
  参考文献：
  名称：

  Reversible inhibition of human acetylcholinesterase by methoxypyridinium species

  摘要：

  The irreversible inhibition of acetylcholinesterase (AChE) by organophosphorous chemical warfare agents necessitates that antidotes be administered for effective treatment. Currently no antidote is known that resurrects the phosphyl-AChE complex once aging has occurred. This report characterizes the affinities of over 30 new AChE inhibitors which could act as resurrecting agents for the aged AChE-OP adduct. (c) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.09.008
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 以90%的产率得到7-(3-hydroxypropoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Reversible inhibition of human acetylcholinesterase by methoxypyridinium species

  摘要：

  The irreversible inhibition of acetylcholinesterase (AChE) by organophosphorous chemical warfare agents necessitates that antidotes be administered for effective treatment. Currently no antidote is known that resurrects the phosphyl-AChE complex once aging has occurred. This report characterizes the affinities of over 30 new AChE inhibitors which could act as resurrecting agents for the aged AChE-OP adduct. (c) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.09.008

文献信息

• Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol release
  作者：R. Adam Mosey、Paul E. Floreancig

  DOI：10.1039/c2ob26571k

  日期：——

  A series of α-alkoxy carbamates that cleave under mild conditions to release alcohols has been synthesized through a multicomponent process. The relationship between structural features in these compounds and the rate of alcohol release in the presence of basic hydrogen peroxide has been studied. The preparation of carbamates that cleave under other conditions has been demonstrated.

  一系列 α-烷氧基氨基甲酸酯在温和条件下裂解以释放醇，已通过多组分工艺合成。这些化合物的结构特征与碱性物质存在下醇释放速率之间的关系过氧化氢已被研究。在其他条件下裂解的氨基甲酸酯的制备已得到证实。
• Quantitative DNA Interstrand Cross-Link Formation by Coumarin and Thymine: Structure Determination, Sequence Effect, and Fluorescence Detection
  作者：Huabing Sun、Heli Fan、Xiaohua Peng

  DOI：10.1021/jo5014756

  日期：2014.12.5

  Quantitative DNA interstrand cross-link (ICL) formation was observed with the coumarin moieties containing a flexible two-carbon or longer chain. DNA cross-linking by coumarins shows a kinetic preference when flanked by an A:T base pair as opposed to a G:C pair. An efficient photoinduced electron transfer between coumarin and dG slows down ICL formation. ICL formation quenches the fluorescence of coumarin

  香豆素类似物已广泛用于医学，生物学，生物化学和材料科学。在这里，我们报告了香豆素对DNA反应性的详细研究。合成了一系列香豆素类似物，并将其掺入寡脱氧核苷酸中。在350 nm照射下，香豆素部分与胸苷之间发生光诱导的[2 + 2]环加成反应，形成顺式和反式环丁烷加合物（17和18），通过254/350 nm的DNA辐照是可光逆的。观察到含有柔性双碳或更长碳链的香豆素部分的定量DNA链间交联（ICL）形成。香豆素的DNA交联在A：T碱基对侧而不是G：C对侧时显示出动力学偏好。香豆素和dG之间有效的光诱导电子转移减慢了ICL的形成。ICL的形成使香豆素的荧光猝灭，这首次通过荧光光谱法实现了对DNA交联和光可逆性的快速，轻松，实时监控。它可用于检测嘧啶和嘌呤之间的转化突变。总的来说，这项工作为香豆素的生化特性和可能的​​毒性提供了新的见解。定量的，可检测荧光的
• Synthesis and fluorescence properties of [60] and [70]fullerene–coumarin dyads: Efficient dipole–dipole resonance energy transfer from coumarin to fullerene
  作者：Maria João Brites、Célia Santos、Susana Nascimento、Bárbara Gigante、Heinrich Luftmann、Aleksandre Fedorov、Mário N. Berberan-Santos

  DOI：10.1039/b601649a

  日期：——

  New [60] and [70]fullerene–coumarin dyads were prepared by covalently linking a coumarin dye to a fullerene (C60 or C70) via a 1,3-dipolar cycloaddition reaction of azomethine ylides or by a cyclopropanation reaction of fullerenes with malonate derivatives. These dyads were spectroscopically characterized and their fluorescence properties studied. Fluorescence quenching of the coumarin fluorophore in the dyads results from efficient dipole–dipole resonance energy transfer from the coumarin moiety to the fullerene moiety.

  新合成的 [60] 和 [70]富勒烯-香豆素二元体通过将香豆素染料共价连接到富勒烯（C60 或 C70）上制备而成，连接方法是通过偶氮甲碱叶立德的1,3-偶极环加成反应或通过富勒烯与丙二酸酯衍生物的环丙烷化反应。这些二元体经过光谱学表征，并研究了它们的荧光性质。香豆素荧光团的荧光猝灭是由于香豆素部分向富勒烯部分有效偶极-偶极共振能量转移所导致的。
• pH-labile and photochemically cross-linkable polymer vesicles from coumarin based random copolymer for cancer therapy
  作者：Pousali Samanta、Kausik Kapat、Saikat Maiti、Gargi Biswas、Santanu Dhara、Dibakar Dhara

  DOI：10.1016/j.jcis.2019.07.069

  日期：2019.11

  process, followed by characterization using NMR and GPC. The said copolymer self-assembled at physiological pH to form vesicular nano-aggregates which was confirmed using DLS, TEM and by fluorescence measurements. These vesicles were further stabilized by photochemical crosslinking via coumarin (2π + 2π) cycloaddition reaction. These cross-linked vesicles (CVs) exhibited a 38% reduction in premature drug

  在生理环境下纳米载体内部药物有效载荷的稳定性以及以可持续的方式在特定肿瘤细胞中释放所述药物是确定智能靶向药物输送系统效率的两个最重要因素。在这项工作中，通过可逆的加成-断裂链转移（RAFT）工艺将甲基丙烯酸2-羟乙酯和含有β-硫代丙酸酯部分的香豆素基甲基丙烯酸酯单体共聚，然后使用NMR和GPC进行表征。所述共聚物在生理pH下自组装形成囊泡纳米聚集体，其通过DLS，TEM和荧光测量证实。这些囊泡通过香豆素（2π+2π）环加成反应通过光化学交联进一步稳定。与未交联的囊泡（UCVs）在生理pH值相比，这些交联的囊泡（CVs）表现出的过早药物泄漏减少了38％。另外，在肿瘤细胞中普遍存在的弱酸性条件下，β-硫代丙酸酯部分的缓慢水解导致囊泡的分解，从而以可持续的方式释放负载的药物。进行了与体外毒性，细胞摄取效率和交联囊泡（CV）中装载的阿霉素（DOX）对癌细胞系的pH响应抗肿瘤活性有关的研究。与针对M
• 青蒿素-香豆素杂合分子及其制备方法和应用
  申请人：沈阳药科大学

  公开号：CN106188088B

  公开（公告）日：2019-03-01

  本发明的目的是提供一种青蒿素‑香豆素杂合分子及其制备方法和用途，提供一种其在药学上可接受的盐、溶剂化物、光学异构体或多晶型物，还提供一种以该衍生物或其盐为活性成分的药物。本发明所涉及的化合物结构式如式（I）或其药学上可接受的盐、溶剂化物、光学异构体或多晶型物：其中，L=O,O(CH2)nO，n=0～3，R1，R2独立地为氢原子，卤素，羟基，C1～C10羧基，C1～C10酯基，氰基，硝基，C1～C10烷基，C1～C10烷氧基，C3～C7环烷基，卤代的C1～C10烷基、C1～C10烷氧基。（I）。