In this study, for the first time, molecular modeling and antiparasitic activity studies were carried out on some azo dyes containing uracil, 6-amino-5-[(4-nitrophenyl) diazenyl] pyrimidine-2,4 (1H, 3H)-dione (dye I) and 6-amino-5-[(4-bromophenyl) diazenyl] pyrimidin-2,4 (1H, 3H)-dione (dye II), which were resynthesized using the same method in the literature and whose molecular structures were confirmed using FTIR and ¹H-NMR methods. In molecular modeling study, all calculations were performed using DFT/B3LYP/6-311++G(d,p) method. The molecular structures of the possible tautomeric forms of dyes I and II were optimized, and their molecular total energies were calculated in the gas phase and DMSO solvent. IR and ¹H-NMR spectral data of the possible tautomeric forms of dyes were obtained, and theoretical spectral data were compared with experimental ones. The evaluations show that, for both dyes, the spectral data of the imine-diketo-hydrazone form, which has the lowest energy and is hence determined to be the most stable form, are in agreement with the experimental ones. In antiparasitic activity study, dyes I and II were tested for the first time against parasites Leishmania infantum, Leishmania major, Leishmania tropica promastigotes, and Trichomonas vaginalis trophozoites. In vitro antileishmanial activities against Leishmania promastigotes were tested by microdilution broth assay with Alamar Blue in RPMI 1640 medium, and in vitro trichomonacidal activities against Trichomonas vaginalis parasite were tested using TYM medium. In tests, antileishmanial and trichomonacidal effects were determined by comparing the obtained minimum inhibitory concentration (MIC) and minimum lethal concentration (MLC) values with those obtained for standard drugs (amphotericin B and metronidazole, respectively).

中文翻译：

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部分含尿嘧啶偶氮染料的DFT研究及抗寄生虫活性

本研究首次对一些含有尿嘧啶、6-氨基-5-[(4-硝基苯基)二氮烯基]嘧啶-2,4 (1H, 3H)-的偶氮染料进行了分子建模和抗寄生虫活性研究。 dione (dye I) 和 6-amino-5-[(4-bromophenyl) dizenyl] pyrimidin-2,4 (1H, 3H)-dione (dye II)，用文献中相同的方法重新合成，其分子使用 FTIR 和¹ H-NMR 方法确认了结构。在分子建模研究中，所有计算均使用 DFT/B3LYP/6-311++G(d,p) 方法进行。优化了染料 I 和 II 可能的互变异构形式的分子结构，并计算了它们在气相和 DMSO 溶剂中的分子总能量。红外和¹获得了染料可能的互变异构形式的 H-NMR 光谱数据，并将理论光谱数据与实验数据进行了比较。评估表明，对于两种染料，具有最低能量并因此被确定为最稳定形式的亚胺-二酮-腙形式的光谱数据与实验数据一致。在抗寄生虫活性的研究中，染料I和II的第一次抗寄生虫进行了测试婴儿利什曼原虫，硕大利什曼原虫，热带利什曼原虫前鞭毛体和阴道毛滴虫滋养体。体外对利什曼原虫的抗利什曼原虫活性通过在 RPMI 1640 培养基中用 Alamar Blue 微量稀释肉汤测定法测试前鞭毛体，并使用 TYM 培养基测试体外对阴道毛滴虫寄生虫的滴虫酸活性。在测试中，通过将获得的最小抑菌浓度 (MIC) 和最小致死浓度 (MLC) 值与标准药物（分别为两性霉素 B 和甲硝唑）获得的值进行比较，确定抗利什曼原虫和滴虫酸作用。