Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds
This paper describes the synthesis of 1,4-dihydropyridine compounds (DHPs) endowed with good muscle relaxant activity and stability to light. Six new condensed DHPs were synthesized by the microwave irradiation method. A long-chain ester moiety [2-(methacryloyloxy)ethyl] and various substituents on...
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2017-09-01
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| Series: | Acta Pharmaceutica |
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| Online Access: | https://doi.org/10.1515/acph-2017-0026 |
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| author | Gündüz Miyase Gözde Ragno Gaetano Şimşek Rahime De Luca Michele Şafak Cihat Grande Fedora El-Khouly Ahmed İşli Fatma Yildirim Şeniz Öztürk Fincan Gökçe Sevim Ioele Giuseppina |
| author_facet | Gündüz Miyase Gözde Ragno Gaetano Şimşek Rahime De Luca Michele Şafak Cihat Grande Fedora El-Khouly Ahmed İşli Fatma Yildirim Şeniz Öztürk Fincan Gökçe Sevim Ioele Giuseppina |
| author_sort | Gündüz Miyase Gözde |
| collection | DOAJ |
| description | This paper describes the synthesis of 1,4-dihydropyridine compounds (DHPs) endowed with good muscle relaxant activity and stability to light. Six new condensed DHPs were synthesized by the microwave irradiation method. A long-chain ester moiety [2-(methacryloyloxy)ethyl] and various substituents on the phenyl ring were demonstrated to affect the muscle relaxant activity occurring in isolated rabbit gastric fundus smooth muscle strips. Forced photodegradation conditions were applied to the molecules according to the ICH rules. The degradation profile of the drugs was monitored by spectrophotometry coupled with the multivariate curve resolution technique. Formation of the oxidized pyridine derivative was observed for all the studied DHPs, except for one compound, which showed very fast degradation and formation of a second photo-product. Pharmacological tests on the molecules showed a good muscle relaxing effect, with a mechanism similar to that of nifedipine, however, proving to be more stable to light. |
| format | Article |
| id | doaj-art-4fe6a3ff1a7844e4b789b2f760aadf09 |
| institution | Kabale University |
| issn | 1846-9558 |
| language | English |
| publishDate | 2017-09-01 |
| publisher | Sciendo |
| record_format | Article |
| series | Acta Pharmaceutica |
| spelling | doaj-art-4fe6a3ff1a7844e4b789b2f760aadf092025-02-02T12:44:02ZengSciendoActa Pharmaceutica1846-95582017-09-0167334135510.1515/acph-2017-0026acph-2017-0026Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compoundsGündüz Miyase Gözde0Ragno Gaetano1Şimşek Rahime2De Luca Michele3Şafak Cihat4Grande Fedora5El-Khouly Ahmed6İşli Fatma7Yildirim Şeniz8Öztürk Fincan Gökçe Sevim9Ioele Giuseppina10Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100, Ankara, TurkeyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036Rende (CS), ItalyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100, Ankara, TurkeyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036Rende (CS), ItalyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100, Ankara, TurkeyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036Rende (CS), ItalyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100, Ankara, TurkeyDepartment of Pharmacology, Faculty of Medicine, Gazi University, 06560, Ankara, TurkeyDepartment of Pharmacology, Faculty of Medicine, Gazi University, 06560, Ankara, TurkeyDepartment of Pharmacology, Faculty of Medicine, Gazi University, 06560, Ankara, TurkeyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036Rende (CS), ItalyThis paper describes the synthesis of 1,4-dihydropyridine compounds (DHPs) endowed with good muscle relaxant activity and stability to light. Six new condensed DHPs were synthesized by the microwave irradiation method. A long-chain ester moiety [2-(methacryloyloxy)ethyl] and various substituents on the phenyl ring were demonstrated to affect the muscle relaxant activity occurring in isolated rabbit gastric fundus smooth muscle strips. Forced photodegradation conditions were applied to the molecules according to the ICH rules. The degradation profile of the drugs was monitored by spectrophotometry coupled with the multivariate curve resolution technique. Formation of the oxidized pyridine derivative was observed for all the studied DHPs, except for one compound, which showed very fast degradation and formation of a second photo-product. Pharmacological tests on the molecules showed a good muscle relaxing effect, with a mechanism similar to that of nifedipine, however, proving to be more stable to light.https://doi.org/10.1515/acph-2017-00261,4-dihydropyridine compoundsmuscle relaxantdrug designstructure activity relationshipphotostabilitymcr analysis |
| spellingShingle | Gündüz Miyase Gözde Ragno Gaetano Şimşek Rahime De Luca Michele Şafak Cihat Grande Fedora El-Khouly Ahmed İşli Fatma Yildirim Şeniz Öztürk Fincan Gökçe Sevim Ioele Giuseppina Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds Acta Pharmaceutica 1,4-dihydropyridine compounds muscle relaxant drug design structure activity relationship photostability mcr analysis |
| title | Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds |
| title_full | Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds |
| title_fullStr | Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds |
| title_full_unstemmed | Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds |
| title_short | Synthesis and photodegradation studies of analogues of muscle relaxant 1,4-dihydropyridine compounds |
| title_sort | synthesis and photodegradation studies of analogues of muscle relaxant 1 4 dihydropyridine compounds |
| topic | 1,4-dihydropyridine compounds muscle relaxant drug design structure activity relationship photostability mcr analysis |
| url | https://doi.org/10.1515/acph-2017-0026 |
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