Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors
The synthesis of phenylene-ethynylene rods and their use as rigid spacers is described. Alternation of a Sonogashira reaction and silyl group cleavage was used to obtain rigid spacers with even and odd numbers of phenylene units. Preliminary applications of these rods in divalent systems are shown....
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.25 |
| _version_ | 1818615945851043840 |
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| author | Francesca Pertici Norbert Varga Arnoud van Duijn Matias Rey-Carrizo Anna Bernardi Roland J. Pieters |
| author_facet | Francesca Pertici Norbert Varga Arnoud van Duijn Matias Rey-Carrizo Anna Bernardi Roland J. Pieters |
| author_sort | Francesca Pertici |
| collection | DOAJ |
| description | The synthesis of phenylene-ethynylene rods and their use as rigid spacers is described. Alternation of a Sonogashira reaction and silyl group cleavage was used to obtain rigid spacers with even and odd numbers of phenylene units. Preliminary applications of these rods in divalent systems are shown. Inhibition studies with Pseudomonas Aeruginosa lectin LecA showed that the rigid spacer proved greatly beneficial for the inhibitory potency. |
| first_indexed | 2024-12-16T16:41:58Z |
| format | Article |
| id | doaj.art-ccc7e6ec21d64e26b6b1451a7eca240c |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T16:41:58Z |
| publishDate | 2013-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-ccc7e6ec21d64e26b6b1451a7eca240c2022-12-21T22:24:16ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-01-019121522210.3762/bjoc.9.251860-5397-9-25Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitorsFrancesca Pertici0Norbert Varga1Arnoud van Duijn2Matias Rey-Carrizo3Anna Bernardi4Roland J. Pieters5Department of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The NetherlandsDipartimento di Chimica, Universita’ degli Studi di Milano, via Golgi 19, 20133 Milano, ItalyDepartment of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The NetherlandsDepartment of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The NetherlandsDipartimento di Chimica, Universita’ degli Studi di Milano, via Golgi 19, 20133 Milano, ItalyDepartment of Medicinal Chemistry and Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, 3508 TB Utrecht, The NetherlandsThe synthesis of phenylene-ethynylene rods and their use as rigid spacers is described. Alternation of a Sonogashira reaction and silyl group cleavage was used to obtain rigid spacers with even and odd numbers of phenylene units. Preliminary applications of these rods in divalent systems are shown. Inhibition studies with Pseudomonas Aeruginosa lectin LecA showed that the rigid spacer proved greatly beneficial for the inhibitory potency.https://doi.org/10.3762/bjoc.9.25multivalent carbohydratesLecA inhibitionphenylene ethynylenerigid spacersSonogashira reaction |
| spellingShingle | Francesca Pertici Norbert Varga Arnoud van Duijn Matias Rey-Carrizo Anna Bernardi Roland J. Pieters Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors Beilstein Journal of Organic Chemistry multivalent carbohydrates LecA inhibition phenylene ethynylene rigid spacers Sonogashira reaction |
| title | Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors |
| title_full | Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors |
| title_fullStr | Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors |
| title_full_unstemmed | Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors |
| title_short | Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors |
| title_sort | efficient synthesis of phenylene ethynylene rods and their use as rigid spacers in divalent inhibitors |
| topic | multivalent carbohydrates LecA inhibition phenylene ethynylene rigid spacers Sonogashira reaction |
| url | https://doi.org/10.3762/bjoc.9.25 |
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