Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides
Novel N-linked 5a–e and O-linked glycopyranosides 7a–e were synthesized in high yield from commercially available L-tartaric acid containing two asymmetric centers and C2 axis of symmetry. The compound L-tartaric acid was completely protected and then partially hydrolyzed to get the monoester, which...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2018-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2018/9648710 |
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| author | Haroon ur Rashid Sher Wali Khan Momin Khan Akhtar Nadhman Noor Rehman Muhammad Tariq Sammer Yousuf |
| author_facet | Haroon ur Rashid Sher Wali Khan Momin Khan Akhtar Nadhman Noor Rehman Muhammad Tariq Sammer Yousuf |
| author_sort | Haroon ur Rashid |
| collection | DOAJ |
| description | Novel N-linked 5a–e and O-linked glycopyranosides 7a–e were synthesized in high yield from commercially available L-tartaric acid containing two asymmetric centers and C2 axis of symmetry. The compound L-tartaric acid was completely protected and then partially hydrolyzed to get the monoester, which upon treatment with different amino and hydroxyl derivatives of glycopyranoses gave the desired amides and esters. The synthesized derivatives were purified by chromatography and characterized by spectroanalytical techniques. The structure of compound 7c in the series was supported by X-ray analysis. Leishmanicidal activities of compounds 5a–e and 7a–e were investigated which showed moderate to good activities. |
| format | Article |
| id | doaj-art-3c46c569c88c48c495d10bd27353dac0 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2018-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-3c46c569c88c48c495d10bd27353dac02025-02-03T00:59:55ZengWileyJournal of Chemistry2090-90632090-90712018-01-01201810.1155/2018/96487109648710Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked GlycopyranosidesHaroon ur Rashid0Sher Wali Khan1Momin Khan2Akhtar Nadhman3Noor Rehman4Muhammad Tariq5Sammer Yousuf6Department of Chemistry, Sarhad University of Science and Information Technology, Peshawar, Khyber Pakhtunkhwa, PakistanDepartment of Chemistry, Shaheed BB University, Sheringal, Upper Dir, Khyber Pakhtunkhwa, PakistanDepartment of Biotechnology, Quaid-I-Azam University, Islamabad 45320, PakistanInstitute of Integrative Biosciences (IIB), CECOS University of Information Technology and Emerging Sciences, Peshawar, Khyber Pakhtunkhwa, PakistanDepartment of Chemistry, Shaheed BB University, Sheringal, Upper Dir, Khyber Pakhtunkhwa, PakistanDepartment of Chemistry, Shaheed BB University, Sheringal, Upper Dir, Khyber Pakhtunkhwa, PakistanH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, PakistanNovel N-linked 5a–e and O-linked glycopyranosides 7a–e were synthesized in high yield from commercially available L-tartaric acid containing two asymmetric centers and C2 axis of symmetry. The compound L-tartaric acid was completely protected and then partially hydrolyzed to get the monoester, which upon treatment with different amino and hydroxyl derivatives of glycopyranoses gave the desired amides and esters. The synthesized derivatives were purified by chromatography and characterized by spectroanalytical techniques. The structure of compound 7c in the series was supported by X-ray analysis. Leishmanicidal activities of compounds 5a–e and 7a–e were investigated which showed moderate to good activities.http://dx.doi.org/10.1155/2018/9648710 |
| spellingShingle | Haroon ur Rashid Sher Wali Khan Momin Khan Akhtar Nadhman Noor Rehman Muhammad Tariq Sammer Yousuf Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides Journal of Chemistry |
| title | Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides |
| title_full | Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides |
| title_fullStr | Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides |
| title_full_unstemmed | Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides |
| title_short | Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides |
| title_sort | synthesis characterization x ray crystallography and antileishmanial activities of n linked and o linked glycopyranosides |
| url | http://dx.doi.org/10.1155/2018/9648710 |
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