Yan, Yugang published the artcileSynthesis of chiral ND-322, ND-364 and ND-364 derivatives as selective inhibitors of human gelatinase, Application In Synthesis of 57044-25-4, the publication is Bioorganic & Medicinal Chemistry (2015), 23(20), 6632-6640, database is CAplus and MEDLINE.
Compounds I.HCl (ND-322) and II (ND-364) are potent selective inhibitors for gelatinases, matrix metalloproteinase 2 (MMP2) and matrix metalloproteinase 9 (MMP9). However, both of them are racemates. Herein the authors report facile synthesis of optically active (R)- and (S)-enantiomers of compounds I.HCl and II. And the sulfonyl of II was transformed to sulfinyl to obtain four epimeric mixtures All synthesized thiirane-based compounds were evaluated in MMP2 and MMP9 inhibitory assays. The results indicated that the configuration of thiirane moiety had little effects on gelatinase inhibition, but the substitution of sulfinyl for sulfonyl was detrimental to gelatinase inhibition. Besides, all target compounds exhibited no inhibition against other two Zn2+ dependent metalloproteases, aminopeptidase N (APN) and histone deacetylases (HDACs), which confirmed the unique Zn2+ chelation mechanism of thiirane moiety against gelatinases.
Bioorganic & Medicinal Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C18H24N6O6S4, Application In Synthesis of 57044-25-4.
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