Modified Coumarins. 19. Synthesis of Neoflavone D-Glycopyranosides

Neoflavone β-D-glucopyranosides, β-D-galactopyranosides, β-D-xylopyranosides, and α-D-arabinopyranosides were synthesized by Michael condensation of potassium salts of 7-hydroxy-4-arylcoumarins with acetobromosugars followed by deacetylation of the resulting peracetates. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 546–550, November–December, 2005.     

Modified Coumarins. 6. Synthesis of Substituted 5,6-Benzopsoralens

Substituted 5H-benzo[c]furo[3,2-g]chromen-5-ones, modified analogs of psoralen that contain a benzene ring annelated at the 5,6-position of a furo[3,2-g]chromen-7-one system, were synthesized from 3-hydroxy- 6H-benzo[c]chromen-6-ones.     

Modified Coumarins. 4. Synthesis and Biological Properties of Cyclopentaneannelated Furocoumarins

Psoralen and allopsoralen analogs that contain an annelated cyclopentane were synthesized from 7-hydroxyand 9-hydroxy-1,2,3,4-tetrahydrocyclopenta[c]chromen-4-ones. 9-Phenyl-1,2,3,4-tetrahydrocyclopenta[c]furo[3,2-g]chromen-4-one exhibited low toxicity, acted as a CNS stimulant, and exhibited cardiotropic activity.     

Modified Coumarins. 18. Synthesis of Angular Dihydropyranocoumarins Containing Amino Acids and Peptides

Angular dihydropyranocoumarins containing natural and synthetic amino acids and dipeptides were synthesized using activated esters. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 422–427, September–October, 2005.     

Modified Coumarins. 7. Synthesis and Biological Activity of Mannich Bases of Substituted 7,8,9,10-Tetrahydrobenzo[c]chromen-6-ones

Condensation of 1- and 3-hydroxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-ones with substituted 1,1- diaminomethanes produced Mannich bases containing a dialkylaminomethyl group in the 2- and 4-positions of 7,8,9,10-tetrahydrobenzo[c]chromen-6-one. Pharmacological screening of 2-chloro-3-hydroxy-4-(1- pyrrolidinylmethyl)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one in Wistar rats showed that it possesses low toxicity and acts as a stimulant of the central and peripheral nervous systems with indications of neuroleptic and tranquilizing activities.     

Modified Coumarins. 11. Synthesis and Biological Activity of Mannich Bases of Substituted 1,3-Dihydrocyclopenta[c]chromen-4-ones

Mannich bases containing the dialkylaminomethyl group in the 6- and 8-positions of 2,3-di-hydrocyclopenta[c]chromen-4-ones were prepared by condensation of 7- and 9-hydroxy-2,3-dihydrocyclopenta[c]chromen-4-ones with substituted 1,1-diaminomethanes. The effects of 8-chloro-7-hydroxy-6-(1-pyrrolidinylmethyl)-2,3-dihydrocyclopenta[c]chromen-4-one and 8-chloro-7-hydroxy-6-(morpholinomethyl)-2,3-dihydrocyclopenta[c]chromen-4-one on the central and peripheral nervous systemwere defined and enable the presence of tranquilizing and neuroleptic properties to be predicted.     

香豆素类抗凝血药及其类似物的合成

香豆素类抗凝血药及其类似物的合成;羟基香豆素;取代苯丁烯酮;缩合;香豆素类似物     

Modified Coumarins. 10. Synthesis of Substituted 2-(7-Oxofuro[3,2-g]chromen-6-yl)acetic Acids

Substituted 2-(7-oxofuro[3,2-g]chromen-6-yl) acetic acids, modified psoralen analogs, were synthesized by linear fusion of a furan ring to the coumarin system.     

Synthesis and Antitumor Activity of Novel Coumarin Derivatives via a Three-component Reaction in Water

An efficient synthesis of novel coumarin derivatives via a three‐component condensation of 4‐hydroxycoumarin, aldehydes and aromatic amines catalyzed by sulfonic acid functionalized ionic liquid L‐2‐(hydroxymethyl)‐1‐(4‐sulfobutyl)pyrrolidinium hydrogen sulfate ([HYSBPI]·HSO₄) is reported. The condensed product was obtained with excellent yields in water under microwave irradiation condition. The antitumor activities of all the synthesized compounds were assessed on two different human cancer cell lines (A‐549 and MCF‐7), and the results showed that these compounds had weak‐to‐good antitumor activities and their IC₅₀ ranged from 0.05 to more than 100 µmol·L^?1.     

Modified Coumarins. 16. Cyclohexane-Annelated Analogs of Pyranocoumarins

Modified derivatives of angular and linear pyranocoumarins containing a condensed cyclohexane moiety were prepared by fusing a 2,2-dimethyltetrahydropyran ring to the coumarin system and annelating a pyrone ring to derivatives of 2,2-dimethylchromane. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 313–318, July–August, 2005.     

Modified coumarins. 28. Synthesis of spirosubstituted pyranocoumarins

Spiropyranobenzopyrandiones were prepared, reduced, and dehydrated to form spirosubstituted pyranocoumarins. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 135–139, March–April, 2009.     

Synthesis and Antibacterial Evaluation of Novel 3,6-Disubstituted Coumarin Derivatives

A novel series of 3,6-disubstituted coumarin derivatives were synthesized by the reaction of ethyl-2-(3-acetyl-2-oxo-2H-chromen-6-yl)-4-methylthiazole-5-carboxylate with thiosemicarbazide and various phenacyl bromides / 3-(2-bromoacetyl)-2H-chromen-2-ones / 2-(2-bromoacetyl)-3H-benzo[f]chromen-3-one in ethanol having catalytic amount of acetic acid under reflux conditions with good yields. All the synthesized compounds were fully characterized by spectral studies and evaluated for their in vitro antibacterial activity against Pseudomonas aeruginosa, Bacillus subtilis (Gram positive), Escherichia coli, and Azatobacter (Gram negative) bacterial strains. Activity results revealed that the compound 6h against Escherichia coli and compound 6i against Pseudomonas aeruginosa and Escherichia coli have shown maximum zones of inhibition. Remaining compounds showed moderate to good activity against all the tested bacterial strains compared with the standard drug cefotaxime.     

The Synthesis of a Series of Phosphoryl Coumarins

Different hydroxy substituted coumarins were successfully phosphorylated with diisopropylphophite （DIPPH） by the Atherton-Todd reaction in 76-89% yields. Moreover, the reaction activities of different hydroxys of the coumarins in the Atherton-Todd reaction were studied.     

Synthesis and Antiproliferative Effect of Halogenated Coumarin Derivatives

A series of 6- and 6,8-halocoumarin derivatives have been investigated as potential antiproliferative compounds against a panel of tumor and normal cell lines. Cytotoxic effects were determined by the MTT method. To investigate the potential molecular mechanism involved in the cytotoxic effect, apoptosis assay, cell cycle analysis, reactive oxygen species (ROS), and reduced glutathione analysis were performed. Among the screened compounds, coumarins 6,8-dibromo-2-oxo-2H-chromene-3-carbonitrile 2h and 6,8-diiodo-2-oxo-2H-chromene-3-carbonitrile 2k exhibited the most antiproliferative effect in thyroid cancer-derived cells TPC-1. The apoptosis assay showed that both 2h and 2k induced apoptosis in TPC-1 thyroid cancer cells. According to these experiments, both coumarins induced a slight increase in TPC-1 cells in the G2/M phase and a decrease in the S phase. A significant increase in ROS levels was observed in TPC-1 treated with diiodocoumarin 2k, while the dibromocoumarin 2h induced a decrease in ROS in a dose and time-dependent manner.     

Dually Activated Organo- and Nano-cocatalyzed Synthesis of Coumarin Derivatives

A wide range of substituted coumarin derivatives were synthesized by refluxing in acetonitrile, ethyl acetoacetate, and ethyl benzoyl acetate with a wide range of structurally diverse phenol derivatives within a short reaction time with a catalytic combination of pyridine dicarboxylic acid as organocatalyst and nanocrystalline ZnO.     

Modified coumarins. 30. Synthesis of 6-heteroarylcoumarins

Heteroarylcoumarins containing 2-indole, 3-pyrazole, and 4-pyrimidine substituents in the 6-position of the coumarin ring were synthesized. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 145-148, March-April, 2009.     

Sulfonated RAFT Copolymers as Heparin Mimetics: Synthesis,Reactivity Ratios,and Anticoagulant Activity

The glycosaminoglycan heparin is a clinically important anticoagulant drug, primarily used to reduce the risk of blood clots (thrombosis) during surgery. Despite its importance in medicine and its continuous use over many decades, heparin suffers from several limitations associated with its heterogeneity and its extraction from animal tissues. In order to address these limitations, reversible addition‐fragmentation chain transfer polymerization is utilized to prepare a library of heparin mimetic copolymers from the sulfonated monomers sodium 4‐styrene sulfonate, potassium‐3‐sulfopropyl acrylate, potassium‐3‐sulfopropyl methacrylate, and sodium‐2‐acrylamido‐2‐methyl‐1‐propane sulfonate. Copolymers are prepared using combinations of two different monomers in various ratios. Monomer reactivity ratios are also determined for some representative monomer combinations, and all polymers are characterized by ¹H NMR spectroscopy and gel permeation chromatography. The anticoagulant activities of the copolymers are determined by activated partial thromboplastin time and thrombin clotting time assays and structure–activity relationships are explored.     

高效液相色谱法对化妆品中17种香豆素类化学成分的同时测定

建立了同时测定化妆品中17种香豆素类化学成分(双香豆素、7-羟基-6-甲氧基香豆素、8-羟基补骨脂素、香豆素、6,7-二甲氧基香豆素、二氢香豆素、7-甲氧基香豆素、7-甲基香豆素、补骨脂素、8-甲氧基补骨脂素、5-甲氧基补骨脂素、4-甲基-7-乙氧基香豆素、2′,4,8-三甲基补骨脂素、欧前胡素、异欧前胡素、二氢欧山芹醇当归酸酯、环香豆素)的高效液相色谱分析方法。样品经甲醇超声提取,以8 000 r/min离心15 min,取上清液过滤后测定。采用Agilent Zorbax SB-Phenyl柱(4.6 mm×250 mm,5μm)分离,以水-甲醇-乙腈三元流动相梯度洗脱,流速1.0 mL/min,柱温30℃。采用二极管阵列检测器多波长检测(210、220、250 nm),外标法定量。17种香豆素类化合物的定量下限(LOQ)为1 mg/kg,线性范围为0.5~60 mg/L,相关系数(r)均大于0.999。在高、中、低3种加标水平下的平均加标回收率(n=6)为86%~106%,相对标准偏差为0.3%~3.6%。该方法准确、简便,适用于化妆品中17种香豆素类化合物的测定。     

Design and Synthesis of a-Cyclodextrin Modified Coumarin

以环氧氯丙烷为桥接,利用水溶性α-环糊精（α-CD）进行7-羟基-4-甲基香豆素的功能化修饰,得到新型α-环糊精修饰型香豆素衍生物（α-CD-C）.用傅里叶变换红外（FT-IR）光谱、氢核磁共振（1H NMR）、液质联用（LC-MS）等对该香豆素衍生物进行了结构表征.紫外光二聚实验表明,该α-环糊精修饰型香豆素可在365 nm光照下进行光二聚反应,且可在随后的254 nm光照下进行解二聚反应;同时通过比较该交替光照下的光二聚反应程度,可知该光二聚反应仅是部分可逆的.