香豆素类衍生物的合成

由人免疫缺陷病毒 ( HIV)感染引起的免疫缺陷综合症 ( AIDS)——艾滋病 ,是人类致命疾病之一。世界各国都在致力于寻找抗艾滋病药物 ,其中一个研究热点是通过大规模筛选寻找生物活性较强的小分子非肽类抑制剂 ,然后进行结构优化 ,以期找到新一代的抗艾滋病药物。香豆素类衍生物是一类具有抗病毒等许多生物活性的化合物 ,一直被人们所重视。 1 992年 ,从马来西亚热带雨林植物 Calophllum L anigerum中分离出具有抗艾滋病病毒活性的香豆素类化合物 Calanolides[1] 。同时 ,由于香豆素类化合物合成相对简单 ,生物利用度高 ,促使人们在这个…     

Synthesis of some new fused coumarin derivatives

2-Hydrazino-4-hydroxy-5H- [1] -benzopyrano- [ 4,3-d ] -pyrim-idin-5-one (3) was prepared via condensation of 2 with hy-drazine hydrate. Treatment of 3 with methylene chloride, ethyl chloroformate, ethyl chloroacetate and benzaldehyde yielded the corresponding 2 - ( substituted ) hydrazino - 4 -hydro-xy-5H-[1]-benzopyrano-[4, 3-d]-pyrimidin-5-one (4, 5, 6, and 10), followed by cyclization of 4, 5 and 6 with dimethyl fonnamide and fused sodium acetate under reflux, while compound 10 was cyclized with bromine and sodium acetate in acetic acid. Compound 3 reacted with β-(toloyl) acrylic acid, ethyl α-cyano-p-methoxytinnamate, diethyl mal-onate and acetyl chloride affording the corresponding 2-(substituted) hydrazino-4-hydroxy-5H-[1]-benzopyrano-[4, 3-d]-pyrimidin-5-one (12, 13, 14, 15 and 16).     

Design,Synthesis, and In Vivo and In Silico Evaluation of Coumarin Derivatives with Potential Antidepressant Effects

In this study, a series of coumarin derivatives were designed and synthesized, their structures were characterized using nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) testing methods. In the pharmacological experiment, two behavior-monitoring methods, the forced swim test (FST) and the tail suspension test (TST), were used to determine the antidepressant activity of coumarin derivatives. Compounds that showed potential activity were analyzed for their effects on 5-hydroxytryptamine (5-HT) levels in the brains of mice. Molecular docking experiments to simulate the possible interaction of these compounds with the 5-HT_1A receptor was also be predicted. The results of the pharmacological experiments showed that most coumarin derivatives exhibited significant antidepressant activity. Among these compounds, 7-(2-(4-(4-fluorobenzyl)piperazin-1-yl)-2-oxoethoxy)-2H-chromen-2-one (6i) showed the highest antidepressant activity. The results of the measurement of 5-HT levels in the brains of mice indicate that the antidepressant activity of coumarin derivatives may be mediated by elevated 5-HT levels. The results of molecular docking demonstrated that compound 6i had a significant interaction with amino acids around the active site of the 5-HT_1A receptor in the homology model. The physicochemical and pharmacokinetic properties of the target compounds were also predicted using Discovery Studio (DS) 2020 and Chemdraw 14.0.     

香豆素类荧光传感器*

荧光传感器能够将分子识别的信息转换成荧光信号,荧光法在灵敏度、选择性和实时原位检测等方面优势突出。实时检测被分析物的水平已引起包括化学家、生物学家、临床生物化学家和环境学家的极大兴趣。以香豆素为基础的荧光传感器近年来已成为一个新兴的研究热点。本文综述了香豆素类荧光传感器在阳离子、阴离子、中性分子识别检测中的分子设计、作用机理和应用效果,展望了该领域的发展方向。     

香豆素和呋喃均三唑并噻二唑化合物的合成

香豆素和呋喃均三唑并噻二唑化合物的合成;香豆素;呋喃;均三唑并噻二唑;合成     

香豆素分子模板聚合物的合成与性能研究

以香豆素为模板分子, α-甲基丙烯酸(MAA)、丙烯酰胺(MA)、2-乙烯基吡啶(2-VP)和4-乙烯基吡啶(4-VP)为功能单体, 二甲基丙烯酸乙二醇酯(EGDMA)为交联剂, 利用分子模板技术分别在甲苯、甲醇、氯仿和乙腈溶剂中合成了一系列香豆素分子模板聚合物(MTP), 研究了聚合体系组成对模板聚合物吸附特性的影响. 结果表明, 在所合成的模板聚合物中, 以MAA为功能单体, 乙腈为致孔溶剂, 以1∶4∶30的摩尔比加入模板分子、MAA及EGDMA时制备的模板聚合物吸附容量高、印迹效果和选择性好. 此模板聚合物有作为白芷样品中香豆素吸附分离材料的应用前景.     

Chemical composition of Erycibe schmidtii and antiproliferative activity of scopoletin on immature dendritic cells

Abstract

Immature dendritic cells (iDCs) play very important roles in the pathological process of rheumatoid arthritis (RA). Therefore, it is urgent to search for natural products with antiproliferative activity on iDCs for anti-RA drug discovery. Erycibe schmidtii, a traditional Chinese medicine, has been used to treat RA in China. Its bioactive ingredients on RA are still unclear. In this study, twenty compounds including a new caffeoylquinic acid derivative, 3-O-caffeoyl-4-O-syringoylquinic acid methyl ester (16), were isolated from E. schmidtii. Their structures were elucidated by NMR and mass spectroscopic analysis, and comparison with literature data. Seventeen compounds were obtained from this plant for the first time, and ten were first found from the genus Erycibe. Scopoletin (1, 5.0?μM) functionally reduced proliferation level of bone marrow immature dendritic cells (BM-iDCs) more than 50%, relative to vehicle. However, scopoletin (1) exhibited no effect on the phagocytosis or survival of BM-iDCs in vitro.     

Antioxidant coumarin and pyrone derivatives from the insect-associated fungus Aspergillus Versicolor

Abstract

Two new compounds, versicolones A and B (1 and 2), and three known pyrone derivatives (3?5) were isolated from the insect-associated fungus Aspergillus versicolor. Their structures were elucidated through a combination of HRESIMS and NMR spectroscopic analysis. Versicolone A (1) was revealed as a coumarin derivative with the rare 5-alkyl side chain substitution. Compound 5 exhibited significant antioxidant activity with EC₅₀ value of 8.0?μM in the ABTS (2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid) assay, which was more than 2-fold potency of the positive control trolox.     

A Cyclometalated IrIII Complex Conjugated to a Coumarin Derivative Is a Potent Photodynamic Agent against Prostate Differentiated and Tumorigenic Cancer Stem Cells

A cyclometalated Ir^III complex conjugated to a far-red-emitting coumarin, Ir^III-COUPY ( 3 ), was recently shown as a very promising photosensitizer suitable for photodynamic therapy of cancer. Therefore, the primary goal of this work was to deepen knowledge on the mechanism of its photoactivated antitumor action so that this information could be used to propose a new class of compounds as drug candidates for curing very hardly treatable human tumors, such as androgen resistant prostatic tumors of metastatic origin. Conventional anticancer chemotherapies exhibit several disadvantages, such as limited efficiency to target cancer stem cells (CSCs), which are considered the main reason for chemotherapy resistance, relapse, and metastasis. Herein, we show, using DU145 tumor cells, taken as the model of hormone-refractory and aggressive prostate cancer cells resistant to conventional antineoplastic drugs, that the photoactivated conjugate 3 very efficiently eliminates both prostate bulk (differentiated) and prostate hardly treatable CSCs simultaneously and with a similar efficiency. Notably, the very low toxicity of Ir^III-COUPY conjugate in the prostate DU145 cells in the dark and its pronounced selectivity for tumor cells compared with noncancerous cells could result in low side effects and reduced damage of healthy cells during the photoactivated therapy by this agent. Moreover, the experiments performed with the 3D spheroids formed from DU145 CSCs showed that conjugate 3 can penetrate the inner layers of tumor spheres, which might markedly increase its therapeutic effect. Also interestingly, this conjugate induces apoptotic cell death in prostate cancer DU145 cells associated with calcium signaling flux in these cells and autophagy. To the best of our knowledge, this is the first study demonstrating that a photoactivatable metal-based compound is an efficient agent capable of killing even hardly treatable CSCs.     

7-氧代-3-苯基香豆素的NMR谱研究

详细归属了三个7-氧代-3-苯基香豆素类衍生物的核磁共振谱(¹1H、¹³C NMR).除7-甲氧基-3-苯基香豆素的¹³C NMR谱外,上述化合物的核磁共振谱均未见报道.