Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines
The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters and alkanamines to afford compounds with intramolecularly hydrogen bonded conformations that mimic substituted purines and therefore are hypothesized to be potential inhibitors of kinases through competitive b...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2008-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/13/12/3149/ |
| _version_ | 1818248277365096448 |
|---|---|
| author | Rosanna Solinas John C. DiCesare Paul W. Baures |
| author_facet | Rosanna Solinas John C. DiCesare Paul W. Baures |
| author_sort | Rosanna Solinas |
| collection | DOAJ |
| description | The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters and alkanamines to afford compounds with intramolecularly hydrogen bonded conformations that mimic substituted purines and therefore are hypothesized to be potential inhibitors of kinases through competitive binding to the ATP site. In this work, a total of 126 dissymmetrically disubstituted imidazole-4,5-dicarboxamides with amino acid ester and alkanamide substituents were prepared by parallel synthesis. The library members were purified by column chromatography on silica gel and the purified compounds characterized by LC-MS with LC detection at 214 nm. A selection of the final compounds was also analyzed by 1H-NMR spectroscopy. The analytically pure final products have been submitted to the Molecular Library Small Molecule Repository (MLSMR) for screening in the Molecular Library Screening Center Network (MLSCN) as part of the NIH Roadmap. |
| first_indexed | 2024-12-12T15:18:02Z |
| format | Article |
| id | doaj.art-8719e0ea0f424d8e8b8d4e4a0aa9a0dc |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T15:18:02Z |
| publishDate | 2008-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8719e0ea0f424d8e8b8d4e4a0aa9a0dc2022-12-22T00:20:27ZengMDPI AGMolecules1420-30492008-12-0113123149317010.3390/molecules13123149Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and AlkanaminesRosanna SolinasJohn C. DiCesarePaul W. BauresThe imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters and alkanamines to afford compounds with intramolecularly hydrogen bonded conformations that mimic substituted purines and therefore are hypothesized to be potential inhibitors of kinases through competitive binding to the ATP site. In this work, a total of 126 dissymmetrically disubstituted imidazole-4,5-dicarboxamides with amino acid ester and alkanamide substituents were prepared by parallel synthesis. The library members were purified by column chromatography on silica gel and the purified compounds characterized by LC-MS with LC detection at 214 nm. A selection of the final compounds was also analyzed by 1H-NMR spectroscopy. The analytically pure final products have been submitted to the Molecular Library Small Molecule Repository (MLSMR) for screening in the Molecular Library Screening Center Network (MLSCN) as part of the NIH Roadmap.http://www.mdpi.com/1420-3049/13/12/3149/ImidazoleNIH RoadmapHeterocyclic scaffoldDrug discovery |
| spellingShingle | Rosanna Solinas John C. DiCesare Paul W. Baures Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines Molecules Imidazole NIH Roadmap Heterocyclic scaffold Drug discovery |
| title | Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines |
| title_full | Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines |
| title_fullStr | Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines |
| title_full_unstemmed | Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines |
| title_short | Parallel Synthesis of an Imidazole-4,5-dicarboxamide Library Bearing Amino Acid Esters and Alkanamines |
| title_sort | parallel synthesis of an imidazole 4 5 dicarboxamide library bearing amino acid esters and alkanamines |
| topic | Imidazole NIH Roadmap Heterocyclic scaffold Drug discovery |
| url | http://www.mdpi.com/1420-3049/13/12/3149/ |
| work_keys_str_mv | AT rosannasolinas parallelsynthesisofanimidazole45dicarboxamidelibrarybearingaminoacidestersandalkanamines AT johncdicesare parallelsynthesisofanimidazole45dicarboxamidelibrarybearingaminoacidestersandalkanamines AT paulwbaures parallelsynthesisofanimidazole45dicarboxamidelibrarybearingaminoacidestersandalkanamines |