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Design, synthesis, and antiplasmodial evaluation of a series of novel sulfoximine analogues of carbohydrate-based thiochromans.
Chemical Biology & Drug Design ( IF 3.2 ) Pub Date : 2018-11-19 , DOI: 10.1111/cbdd.13408 Munashe Chizema 1 , Tommy F Mabasa 1 , Heinrich C Hoppe 2 , Henok H Kinfe 1
Chemical Biology & Drug Design ( IF 3.2 ) Pub Date : 2018-11-19 , DOI: 10.1111/cbdd.13408 Munashe Chizema 1 , Tommy F Mabasa 1 , Heinrich C Hoppe 2 , Henok H Kinfe 1
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Sulfone/sulfoxide-containing carbohydrate derived thiochromans were found to be highly active antiplasmodial agents. However, the inability of the sulfone/sulfoxide functional groups for further derivatization and manipulation limited the potential for further exploration. In this study, based on the interesting and important physicochemical properties, as well as amenability of sulfoximines (isosters of sulfones) for further derivatization, a series of novel sulfoximine-type carbohydrate-derived thiochroman derivatives have been successfully synthesized, characterized, and evaluated for their antiplasmodial activity. Although the replacement of the sulfone functional group with a sulfoximine unit improved the antiplasmodial activity of the scaffolds, the activity was highly dependent on the configuration of the stereogenic centre at the sulfur atom. Moreover, analysis of the crystal structures of the sulfoximine analogues revealed that the bond between the sulfur and nitrogen atoms of the sulfoximine functional group is not a true double bond but rather a polarized single bond.
中文翻译：
设计，合成，和抗疟原虫评估一系列新型的基于碳水化合物的硫代色胺的亚砜亚胺类似物。
发现含砜/亚砜的碳水化合物衍生的硫氰酸盐是高度活性的抗疟原虫剂。但是，砜/亚砜官能团无法进一步衍生化和处理，限制了进一步探索的潜力。在这项研究中，基于有趣而重要的理化性质，以及对亚砜亚砜（砜的异构体）的进一步衍生化的适应性，已成功合成，表征和评估了一系列新颖的亚砜亚胺类碳水化合物衍生的硫代铬烷衍生物。它们的抗血浆活性。尽管用磺胺嘧啶单元取代砜官能团可改善支架的抗血浆活性，活性高度依赖于硫原子上的立体中心的构型。此外，对亚砜亚胺类似物的晶体结构的分析表明，亚砜亚胺官能团的硫原子和氮原子之间的键不是真正的双键，而是极化的单键。
更新日期：2018-11-19
中文翻译：
设计，合成，和抗疟原虫评估一系列新型的基于碳水化合物的硫代色胺的亚砜亚胺类似物。
发现含砜/亚砜的碳水化合物衍生的硫氰酸盐是高度活性的抗疟原虫剂。但是，砜/亚砜官能团无法进一步衍生化和处理，限制了进一步探索的潜力。在这项研究中，基于有趣而重要的理化性质，以及对亚砜亚砜（砜的异构体）的进一步衍生化的适应性，已成功合成，表征和评估了一系列新颖的亚砜亚胺类碳水化合物衍生的硫代铬烷衍生物。它们的抗血浆活性。尽管用磺胺嘧啶单元取代砜官能团可改善支架的抗血浆活性，活性高度依赖于硫原子上的立体中心的构型。此外，对亚砜亚胺类似物的晶体结构的分析表明，亚砜亚胺官能团的硫原子和氮原子之间的键不是真正的双键，而是极化的单键。
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