一些s -衍生物4-R-5-((((3-(吡啶-4-基)- 1h -1,2,4-三唑-5-基)硫(甲基)- 4h -1,2,4-三唑-3-硫醇的光学活性研究

Ye. O. Karpun, S. O. Borsuk, L. I. Kucherenko, V. Parchenko
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引用次数: 0

摘要

目前生产的药物中约有一半是手性化合物,其中约90%以外消旋体的形式出售,由两种对映体的等摩尔混合物组成。手性物质的光学异构体虽然具有相同的化学结构,但大多数在生物活性上存在显著差异。众所周知,单个不对称原子的存在几乎已经成为先进药物设计的一个组成部分。本工作的目的是确定4-R-5-((((3-(吡啶-4-基)- 1h -1,2,4-三唑-5-基)硫(甲基))- 4h -1,2,4-三唑-3-硫醇的一些s -衍生物溶液的偏振面旋转角度,并建立所研究分子的结构与光学活性之间的规律。材料和方法。研究对象为2-[5-R1-4R2-1,2,4-三唑-3-基硫]-1-芳基醇。采用Atago AP-300型偏振光计和DFU 2.2.7理化分析方法“旋光”,对新合成化合物溶液的偏振面旋光角进行了研究。理化分析结果表明,所研究的化合物具有光学活性。化合物1 - ((4-methyl-5 - (((3 - (pyridin-4-yl)的h - 1, 2, 4-triazole-5-yl)含硫的)甲基)4 h, 2, 4-triazole-3-yl)含硫的)2-phenylethan-1-ol(+ 43°[度∙克/立方厘米∙dm])。唯一的左旋物质是1-(4-氟苯基)-2-((4-甲基-5-((3-(吡啶-4-基))- 1h -1,2,4-三唑-5-基)硫)-甲基)- 4h -1,2,4-三唑-3-基)硫)乙二醇,具有比旋度[α]D20 = -43°[deg∙g/cm3∙dm]。研究表明,1-(4-氟苯基)-2-((4-甲基-5-((3-(吡啶-4-基)- 1h -1,2,4-三唑-5-基))硫(甲基)- 4h -1,2,4-三唑-3-基)硫)乙比-1-醇能够使光偏振面向左旋转,这证明了s -对映体在外消旋混合物中的优势,因此该化合物具有进一步临床前研究的可观兴趣。此外,所有其他被分析的化合物表现为光学异构体。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
The study of the optical activity of some S-derivatives 4-R-5-((((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl)thio)methyl)-4H-1, 2,4-triazole-3-thiols
About half of the drugs currently produced are chiral compounds, and about 90 % of these compounds are sold as racemates, consisting of an equimolar mixture of two enantiomers. Although they have the same chemical structure, most of the optical isomers of chiral substances show marked differences in biological activity. It is known that the presence of a single asymmetric atom has become almost an integral part of advanced drug design. The aim of this work was to determine the angle of rotation of the polarization plane of solutions of some S-derivatives of 4-R-5-((((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl)thio)methyl))-4H-1,2,4-triazole-3-thiols and the establishment of regularities between the structure of the studied molecules and their optical activity. Materials and methods. The subject of the study was 2-[5-R1-4R2-1,2,4-triazole-3-ylthio]-1-aryletanols. The study of the angle of rotation of the plane of polarization of solutions of newly synthesized compounds was carried out using an Atago AP-300 polarimeter and the DFU 2.2.7 physical-chemical analysis method “Optical rotation”. Results. The results of the physical-chemical analysis were carried out that the studied compounds exhibit optical activity. The compound 1-((4-methyl-5-(((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl)thio)methyl)-4H-1,2,4-triazole-3-yl)thio)-2-phenylethan-1-ol (+43° [deg∙g/cm3∙dm]). The only levorotatory substance was 1-(4-fluorophenyl)-2-((4-methyl-5-(((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl)thio))methyl)-4H-1,2,4-triazole-3-yl)thio)ethan-1-ol with specific rotation [α]D20 = -43° [deg∙g/cm3∙dm]. Conclusions. Studies had shown that 1-(4-fluorophenyl)-2-((4-methyl-5-(((3-(pyridin-4-yl)-1H-1,2,4-triazole-5-yl))thio)methyl)-4H-1,2,4-triazole-3-yl)thio)ethan-1-ol was able to rotate the light polarization plane to the left, which was evidence of the advantage of the S-enantiomer in the racemic mixture, and therefore this compound was considerable interest for further preclinical research. Also, all other analyzed compounds behave as optical isomers.
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