Synthesis and antiviral activity of 4-quinolinecarboxylic acid hydrazides

Antiviral agents were sought by using ethyl esters of 2-R-4-quinolinecarboxylic acids to synthesize the corresponding aryl (heteryl) hydrazides. 2-Methyl-4-quinolinecarboxylic acid hydrazide was used to synthesize vinylogs containing a nitro group in the substituent. The resulting compounds were tested for antiviral activity against ECHO virus type 6. Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 42, No. 10, pp. 21–23, October, 2008.     

Synthesis and anticholinesterase activity of fluorine-containing α-aminophosphosphoryl compounds

Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 26, No. 6, pp. 21–23, June, 1992.     

十八烷氧乙基替诺福韦酯的合成及抗病毒活性研究

目的:研究十八烷氧乙基替诺福韦酯的合成及其抗病毒活性.方法:以替诺福韦为原料,与脂性侧链2-十八烷氧基-1-乙醇反应得到目标化合物.通过细胞培养法对其体外抗HIV、HBV活性进行测定;通过血清药理学研究,测定小鼠血清的抗HIV-1作用.结果:合成得到了目标化合物十八烷氧乙基替诺福韦酯,其结构经过核磁共振谱和质谱的确证;...     

Synthesis and antiviral activity of phosphonium salts

Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 24, No. 6, pp. 28–30, June, 1990.     

Synthesis and antiviral activity of helioxanthin analogues

A series of natural product analogues based on helioxanthin (2), with particular attention to modification of the lactone ring and methylenedioxy group, were synthesized and evaluated for their antiviral activities. Among them, lactam derivative 18 and helioxanthin cyclic hydrazide 28 exhibited significant in vitro antiviral activity against hepatitis B virus (EC(50) = 0.08 and 0.03 microM, respectively). Compound 18 showed the most potent antiviral activity against hepatitis C virus (55% inhibition at 1.0 microM). Compound 12, an acid-hydrolyzed product of helioxanthin cyclic imide derivative 9, was found to exhibit broad-spectrum antiviral activity against hepatitis B virus (EC(50) = 0.8 microM), herpes simplex virus type 1 (EC(50) = 0.15 microM) and type 2 (EC(50) < 0.1 microM), Epstein-Barr virus (EC(50) = 9.0 microM), and cytomegalovirus (EC(50) = 0.45 microM). Helioxanthin lactam derivative 18 also showed marked inhibition of herpes simplex virus type 1 (EC(50) = 0.29 microM) and type 2 (EC(50) = 0.16 microM). The cyclic hydrazide derivative of helioxanthin 28 and its brominated product 42 exhibited moderately potent activities against human immunodeficiency virus (EC(50) = 2.7 and 2.5 microM, respectively). Collectively, these molecules represent a novel set of antiviral compounds with unique structural features.     

Synthesis and antiviral activity of oxaselenolane nucleosides

As dioxolane and oxathiolane nucleosides have exhibited promising antiviral and anticancer activities, it was of interest to synthesize isoelectronically substituted oxaselenolane nucleosides, in which the 3'-CH(2) is replaced by a selenium atom. To study structure-activity relationships, various pyrimidine and purine oxaselenolane nucleosides were synthesized from the key intermediate, (+/-)-2-benzoyloxymethyl-1,2-oxaselenolane 5-acetate (6). Among the synthesized racemic nucleosides, cytosine and 5-fluorocytosine analogues exhibited potent anti-HIV and anti-HBV activities. It was of interest to obtain the enantiomerically pure isomers to determine if they have differential antiviral activities. However, due to the difficult and time-consuming nature of enantiomeric synthesis, a chiral HPLC separation was performed to obtain optical isomers from the corresponding racemic mixtures. Each pair of enantiomers of Se-ddC and Se-FddC was separated by an amylose chiral column using a mobile phase of 100% 2-propanol. The results indicate that most of the anti-HIV activity of both cytosine and fluorocytosine nucleosides resides with the (-)-isomers.     

Synthesis and antiviral activity of antipyrine derivatives

Translated from Khimiko-farmatsevitcheskii Zhurnal, Vol. 26, No. 5, pp. 5–53, May, 1992.     

Synthesis and antiviral activity of 5-methoxybenzofurans

Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 23, No. 2, pp. 191–195, February, 1989.