4-Hydroxy-2-quinolones. 47. Synthesis and Diuretic Activity of (2H-1,2,4-Benzothiadiazine-1,1-dioxide-3-yl)methylamides of 1-R-4-Hydroxy-2-oxoquinoline-3-carboxylic Acids

With the aim of investigating the relationship between chemical structure and biological activity we have synthesized and studied the effect of (2H-1,2,4-benzothiadiazine-1,1-dioxide-3-yl)methylamides of 1-R-4-hydroxy-2-oxoquinoline-3-carboxylic acids on kidney urinary output.     

Electron ionization-induced fragmentation of N- and O-alkoxymethylated carbostyril and phenanthridinone

Unimolecular fragmentation patterns of N-alkoxymethylated carbostyril and phenanthridinone and their O-alkoxymethyl isomers were studied. The main fragmentation reaction observed for the studied compounds is the elimination of an aldehyde molecule. The main products of this reaction are the appropriate N-methyl derivatives, but ions with other structures are also formed. This reaction is supposed to proceed via 1,3-H shift in the alkoxymethyl group in the case of the N-alkoxymethyl derivatives and by a multi-step mechanism for O-alkoxymethylated compounds. Another important fragmentation common for all studied compounds is the loss of an alkyl radical from N- and O-alkoxymethyl groups, yielding the appropriate stable isomeric cations, which, according to the results of the further fragmentation, undergo fast equilibration reaction via an ion–neutral complex. This process is accompanied by the unusually high kinetic energy release value. Copyright © 2004 John Wiley & Sons, Ltd.     

A Facile and Rapid Method for Preparation of Thiazine and Thiadiazine Derivatives by Sonication Technique

Ultrasound accelerated synthesis of 2,3-(substituted)benzo-1,4-thiazino[5,6-b]-4H-9H-7- methyl-10-oxoquinolines (4), 7-substituted-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin- 4-one (5), 4-substituted-3,9, 10-trihydro-11-oxo-quinolino[2,3-b]-1,3,4-thiadiazino[2,3-d]- 1,2,4-triazole (6), and 7,7-dimethyl-7,8-dihydro-3H,5H,6H-1,2,4-triazolo[3,4-b][1,3,4] benzothiadiazin-9-one (7) from carbostyril and dimedone using sulfur powder and iodine as a catalyst in THF is reported. The structures of the compounds have been elucidated on the basis of spectral and elemental analysis.     

Lanthanide(III) Complexes of Cyclen Triacetates and Triamides Bearing Tertiary Amide-Linked Antennae

The coordination compounds of the trivalent lanthanide ions (Ln(III)) have unique photophysical properties. Ln(III) excitation is usually performed through a light-harvesting antenna. To enable Ln(III)-based emitters to reach their full potential, an understanding of how complex structure affects sensitization and quenching processes is necessary. Here, the role of the linker between the antenna and the metal binding fragment was studied. Four macrocyclic ligands carrying coumarin 2 or 4-methoxymethylcarbostyril sensitizing antennae linked to an octadentate macrocyclic ligand binding site were synthesized. Complexation with Ln(III) (Ln = La, Sm, Eu, Gd, Tb, Yb and Lu) yielded species with overall −1, 0, or +2 and +3-charge. Paramagnetic ¹H NMR spectroscopy indicated subtle differences between the coumarin- and carbostyril-carrying Eu(III) and Yb(III) complexes. Cyclic voltammetry showed that the effect of the linker on the Eu(III)/Eu(II) apparent reduction potential was dependent on the electronic properties of the N-substituent. The Eu(III), Tb(III) and Sm(III) complexes were all luminescent. Coumarin-sensitized complexes were poorly emissive; photoinduced electron transfer was not a major quenching pathway in these species. These results show that seemingly similar emitters can undergo very different photophysical processes, and highlight the crucial role the linker can play.     

4-Hydroxy-2-quinolones. 38. Synthesis, structure, and anticonvulsant activity of optically active 1-phenylethylamides of 1-R-4-hydroxy-2-oxo-3-quinolinecarboxylic acids

A synthesis is reported for optically pure antipodes of 1-phenylethylamides of 1-R-4-hydroxy-2-oxo-3-quinolinecarboxylic acids. An attempt was made to establish the absolute configuration of these products by X-ray diffraction crystallographic analysis. The anticonvulsant activity of the S-enantiomers was studied.For Communication 37, see ref. [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 55–63, January, 2000.     

4-Hydroxy-2-quinolones. 39. Structure of 6-bromo-4-hydroxy-1-isoamyl-2-oxo-3-quinolinecarboxylic acid

S-(–)-1-phenylethylamide of 6-bromo-4-hydroxy-1-isoamyl-2-oxo-3-quinolinecarboxylic acid was synthesized. X-ray diffraction investigation of this product was carried out to determine its absolute configuration.For communication 38, see ref. [1].National Pharmaceutical Academy of Ukraine, 310002 Kharkov, Ukraine Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 64–69, January, 2000.     

双极绿色磷光主体材料1-甲基-3-[4-(9-咔唑基)苯基]-4-苯基喹啉-2(1H)-酮的合成与性能研究

设计并合成了一种基于喹诺酮衍生物的双极绿色磷光主体材料1-甲基-3-[4-(9-咔唑基)苯基]-4-苯基喹啉-2(1 H)-酮.计算发现,化合物的HOMO轨道的电子云位于咔唑基团,LUMO轨道的电子云位于喹诺酮基团,是一种良好的双极材料.化合物的磷光发射峰为515 nm(2.41 eV),符合绿色磷光主体材料的基本要求(>2.4 eV).热失重和差热分析结果表明,该化合物具有较高的热稳定性,分解温度和玻璃化转变温度分别为312℃和105℃.研究结果表明:该新型化合物是一种潜在的具有双极特性的绿色磷光主体材料.