Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products
“Drug likeness” of a molecule is the prime criterion for a molecule to exhibit the desired pharmaceutical activity. A pharmacophore, which describes molecular features that are necessary for molecular recognition of a ligand by a biological macromolecule, is well altered by the Structure Activity Re...
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2016
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| Online Access: | http://hdl.handle.net/11073/25050 |
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| _version_ | 1864513436264693760 |
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| author | Viswanathan, Radhakrishnan |
| author2 | Abu-Yousef, Imad Majdalawieh, Amin Das, Prince Edwin Narasimhan, Srinivasan |
| author2_role | author author author author |
| author_facet | Viswanathan, Radhakrishnan Abu-Yousef, Imad Majdalawieh, Amin Das, Prince Edwin Narasimhan, Srinivasan |
| author_role | author |
| dc.creator.none.fl_str_mv | Viswanathan, Radhakrishnan Abu-Yousef, Imad Majdalawieh, Amin Das, Prince Edwin Narasimhan, Srinivasan |
| dc.date.none.fl_str_mv | 2016 2022-10-25T08:26:27Z 2022-10-25T08:26:27Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | Vishwanathan R, Abu-Yousef IA, Majdalawieh A, Das PE, Narasimhan S. (2016) Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products. Mediterranean Journal of Chemistry 5(3):450-457. http://www.medjchem.com/index.php/medjchem/article/viewFile/427/399. 2028-3997 http://hdl.handle.net/11073/25050 10.13171/mjc53/016041721/abuyousef |
| dc.language.none.fl_str_mv | en_US |
| dc.publisher.none.fl_str_mv | PKP |
| dc.relation.none.fl_str_mv | http://dx.doi.org/10.13171/mjc53/016041721/abuyousef |
| dc.subject.none.fl_str_mv | SAR (Structure Activity Relationship) HLB (Hydrophobic Lipophilic Balance) HTS (High Throughput Screening) Metal borohydrides (MBH 4 ) Metathesis |
| dc.title.none.fl_str_mv | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products |
| dc.type.none.fl_str_mv | Peer-Reviewed Published version info:eu-repo/semantics/publishedVersion info:eu-repo/semantics/article |
| description | “Drug likeness” of a molecule is the prime criterion for a molecule to exhibit the desired pharmaceutical activity. A pharmacophore, which describes molecular features that are necessary for molecular recognition of a ligand by a biological macromolecule, is well altered by the Structure Activity Relationship (SAR) guidelines through Hydrophobic Lipophilic Balance (HLB) demonstrated by the system. The tailoring is best accomplished by organic functional group interconversion on a potent natural product via a variety of synthetic methodologies available to date. Metal borohydrides (MBH₄) in particular are promising compounds as they can potentially serve varying HLB systems. The reagent acts on the substrate to cause reduction, hydroboration, or a combination of both outcomes for the purpose of rearrangement and fragmentation. Indeed, Zr(BH₄)₄ is expected to be more active and selective as a reducing agent compared to NaBH₄ . This study aims at evaluating zirconium borohydride (Zr(BH₄)₄ ) in tetrahydrofuran (THF) as a reducing system to realize a more selective, meaningful and combinatorial osthol (OST) library from potential natural products and attempt to alternate preparation of the same in THF from known metal borohydrides, limiting reduction of the metal center versus metathesis. |
| format | article |
| id | aus_b42b98a7c66077d409ac9c6bba8c8f49 |
| identifier_str_mv | Vishwanathan R, Abu-Yousef IA, Majdalawieh A, Das PE, Narasimhan S. (2016) Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products. Mediterranean Journal of Chemistry 5(3):450-457. http://www.medjchem.com/index.php/medjchem/article/viewFile/427/399. 2028-3997 10.13171/mjc53/016041721/abuyousef |
| language_invalid_str_mv | en_US |
| network_acronym_str | aus |
| network_name_str | aus |
| oai_identifier_str | oai:repository.aus.edu:11073/25050 |
| publishDate | 2016 |
| publisher.none.fl_str_mv | PKP |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| spelling | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural productsViswanathan, RadhakrishnanAbu-Yousef, ImadMajdalawieh, AminDas, Prince EdwinNarasimhan, SrinivasanSAR (Structure Activity Relationship)HLB (Hydrophobic Lipophilic Balance)HTS (High Throughput Screening)Metal borohydrides (MBH 4 )Metathesis“Drug likeness” of a molecule is the prime criterion for a molecule to exhibit the desired pharmaceutical activity. A pharmacophore, which describes molecular features that are necessary for molecular recognition of a ligand by a biological macromolecule, is well altered by the Structure Activity Relationship (SAR) guidelines through Hydrophobic Lipophilic Balance (HLB) demonstrated by the system. The tailoring is best accomplished by organic functional group interconversion on a potent natural product via a variety of synthetic methodologies available to date. Metal borohydrides (MBH₄) in particular are promising compounds as they can potentially serve varying HLB systems. The reagent acts on the substrate to cause reduction, hydroboration, or a combination of both outcomes for the purpose of rearrangement and fragmentation. Indeed, Zr(BH₄)₄ is expected to be more active and selective as a reducing agent compared to NaBH₄ . This study aims at evaluating zirconium borohydride (Zr(BH₄)₄ ) in tetrahydrofuran (THF) as a reducing system to realize a more selective, meaningful and combinatorial osthol (OST) library from potential natural products and attempt to alternate preparation of the same in THF from known metal borohydrides, limiting reduction of the metal center versus metathesis.PKP2022-10-25T08:26:27Z2022-10-25T08:26:27Z2016Peer-ReviewedPublished versioninfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfVishwanathan R, Abu-Yousef IA, Majdalawieh A, Das PE, Narasimhan S. (2016) Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products. Mediterranean Journal of Chemistry 5(3):450-457. http://www.medjchem.com/index.php/medjchem/article/viewFile/427/399.2028-3997http://hdl.handle.net/11073/2505010.13171/mjc53/016041721/abuyousefen_UShttp://dx.doi.org/10.13171/mjc53/016041721/abuyousefoai:repository.aus.edu:11073/250502024-08-22T11:59:52Z |
| spellingShingle | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products Viswanathan, Radhakrishnan SAR (Structure Activity Relationship) HLB (Hydrophobic Lipophilic Balance) HTS (High Throughput Screening) Metal borohydrides (MBH 4 ) Metathesis |
| status_str | publishedVersion |
| title | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products |
| title_full | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products |
| title_fullStr | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products |
| title_full_unstemmed | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products |
| title_short | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products |
| title_sort | Efficient and simple protocol employing borohydride systems to design a selective osthol-zirconium (OST-Zr) library from potential natural products |
| topic | SAR (Structure Activity Relationship) HLB (Hydrophobic Lipophilic Balance) HTS (High Throughput Screening) Metal borohydrides (MBH 4 ) Metathesis |
| url | http://hdl.handle.net/11073/25050 |