Sher Wali Khan, Saira Nayab, Muhammad Naveed Umar, Momin Khan, Anila Iqbal, Nasir Ahmad, Haroon ur Rashid, Muhammad Ishaq Ali Shah, Naila Gulfam, Muhammad Zahoor, Riaz Ullah, Essam A. Ali
{"title":"作为潜在抗菌剂、抗真菌剂和抗利什曼病剂的新型糖共轭物的合成、表征、硅学和体外研究","authors":"Sher Wali Khan, Saira Nayab, Muhammad Naveed Umar, Momin Khan, Anila Iqbal, Nasir Ahmad, Haroon ur Rashid, Muhammad Ishaq Ali Shah, Naila Gulfam, Muhammad Zahoor, Riaz Ullah, Essam A. Ali","doi":"10.1515/chem-2023-0195","DOIUrl":null,"url":null,"abstract":"In the present work, several new glycoconjugates (8a–e) were generated from glycopyranosyl-α-trichloroacetimidates (sugar-OTCA) as glycosyl donors and dimethyl-<jats:sc>l</jats:sc>-tartrate as an aglycone acceptor in good to excellent yields. In the synthetic protocol, various monosaccharides were transformed into pentaacetylated derivatives and then into glycopyranosyl-α-trichloroacetimidates. Afterward, the sugar-OTCA was reacted with dimethyl-<jats:sc>l</jats:sc>-tartrate using Schmidt’s trichloroacetimidate protocol to give the desired products. The newly synthesized glycoconjugates were characterized by FT-IR, <jats:sup>1</jats:sup>H, and <jats:sup>13</jats:sup>C-NMR spectroscopic analytical methods. All the target compounds (8a–e) were tested <jats:italic>in vitro</jats:italic> against various strains of bacteria and fungi at different concentrations. The results revealed that the target compounds had encouraging antibacterial and antifungal potential. The antileishmanial activity of the target compounds against Leishmania tropica promastigotes was also investigated. The <jats:italic>in vitro</jats:italic> results were further supported by the <jats:italic>in silico</jats:italic> docking study that indicated minimum values of the docking scores and binding energies for the resulting complexes obtained by the favorable interactions between the target compounds (8a–e) and the selected strains of bacteria and fungi. The docking results proposed promising antibacterial and antifungal activities of the target compounds (8a–e) against the selected bacterial and fungal species.","PeriodicalId":19520,"journal":{"name":"Open Chemistry","volume":null,"pages":null},"PeriodicalIF":2.1000,"publicationDate":"2024-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis, characterization, in silico and in vitro studies of novel glycoconjugates as potential antibacterial, antifungal, and antileishmanial agents\",\"authors\":\"Sher Wali Khan, Saira Nayab, Muhammad Naveed Umar, Momin Khan, Anila Iqbal, Nasir Ahmad, Haroon ur Rashid, Muhammad Ishaq Ali Shah, Naila Gulfam, Muhammad Zahoor, Riaz Ullah, Essam A. Ali\",\"doi\":\"10.1515/chem-2023-0195\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"In the present work, several new glycoconjugates (8a–e) were generated from glycopyranosyl-α-trichloroacetimidates (sugar-OTCA) as glycosyl donors and dimethyl-<jats:sc>l</jats:sc>-tartrate as an aglycone acceptor in good to excellent yields. In the synthetic protocol, various monosaccharides were transformed into pentaacetylated derivatives and then into glycopyranosyl-α-trichloroacetimidates. Afterward, the sugar-OTCA was reacted with dimethyl-<jats:sc>l</jats:sc>-tartrate using Schmidt’s trichloroacetimidate protocol to give the desired products. The newly synthesized glycoconjugates were characterized by FT-IR, <jats:sup>1</jats:sup>H, and <jats:sup>13</jats:sup>C-NMR spectroscopic analytical methods. All the target compounds (8a–e) were tested <jats:italic>in vitro</jats:italic> against various strains of bacteria and fungi at different concentrations. The results revealed that the target compounds had encouraging antibacterial and antifungal potential. The antileishmanial activity of the target compounds against Leishmania tropica promastigotes was also investigated. The <jats:italic>in vitro</jats:italic> results were further supported by the <jats:italic>in silico</jats:italic> docking study that indicated minimum values of the docking scores and binding energies for the resulting complexes obtained by the favorable interactions between the target compounds (8a–e) and the selected strains of bacteria and fungi. The docking results proposed promising antibacterial and antifungal activities of the target compounds (8a–e) against the selected bacterial and fungal species.\",\"PeriodicalId\":19520,\"journal\":{\"name\":\"Open Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-02-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Open Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1515/chem-2023-0195\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Open Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1515/chem-2023-0195","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Synthesis, characterization, in silico and in vitro studies of novel glycoconjugates as potential antibacterial, antifungal, and antileishmanial agents
In the present work, several new glycoconjugates (8a–e) were generated from glycopyranosyl-α-trichloroacetimidates (sugar-OTCA) as glycosyl donors and dimethyl-l-tartrate as an aglycone acceptor in good to excellent yields. In the synthetic protocol, various monosaccharides were transformed into pentaacetylated derivatives and then into glycopyranosyl-α-trichloroacetimidates. Afterward, the sugar-OTCA was reacted with dimethyl-l-tartrate using Schmidt’s trichloroacetimidate protocol to give the desired products. The newly synthesized glycoconjugates were characterized by FT-IR, 1H, and 13C-NMR spectroscopic analytical methods. All the target compounds (8a–e) were tested in vitro against various strains of bacteria and fungi at different concentrations. The results revealed that the target compounds had encouraging antibacterial and antifungal potential. The antileishmanial activity of the target compounds against Leishmania tropica promastigotes was also investigated. The in vitro results were further supported by the in silico docking study that indicated minimum values of the docking scores and binding energies for the resulting complexes obtained by the favorable interactions between the target compounds (8a–e) and the selected strains of bacteria and fungi. The docking results proposed promising antibacterial and antifungal activities of the target compounds (8a–e) against the selected bacterial and fungal species.
期刊介绍:
Open Chemistry is a peer-reviewed, open access journal that publishes original research, reviews and short communications in the fields of chemistry in an ongoing way. The central goal is to provide a hub for researchers working across all subjects to present their discoveries, and to be a forum for the discussion of the important issues in the field. The journal is the premier source for cutting edge research in fundamental chemistry and it provides high quality peer review services for its authors across the world. Moreover, it allows for libraries everywhere to avoid subscribing to multiple local publications, and to receive instead all the necessary chemistry research from a single source available to the entire scientific community.