Synthesis of Selective β-Lactam Derivatives
In this work, the mild conditions of Mitsunobu reaction were used to convert the hydroxyl group of 6-triphenylmethylaminopenicillanyl alcohol to amines by using different nuleophiles such as phthalimide, di-tert-butyliminodicarboxylate and potassium cyanate. The existence of the β-lactam carbonyl gr...
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| Format: | Article |
| Language: | English |
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An-Najah National University
2012-11-01
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| Series: | مجلة جامعة النجاح للأبحاث العلوم الطبيعية |
| Online Access: | https://journals.najah.edu/media/journals/full_texts/synthesis-selective-b-lactam-derivatives.pdf |
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| author | Iyad Ali Nina Sakhnini |
| author_facet | Iyad Ali Nina Sakhnini |
| author_sort | Iyad Ali |
| collection | DOAJ |
| description | In this work, the mild conditions of Mitsunobu reaction were used to convert the hydroxyl group of 6-triphenylmethylaminopenicillanyl alcohol to amines by using different nuleophiles such as phthalimide, di-tert-butyliminodicarboxylate and potassium cyanate. The existence of the β-lactam carbonyl group increased the instability towards nucleophilic attack of refluxing methanol and the four-membered ring was opened. Treating 3-Di-tert-Butoxycarbonylaminomethyl-6-triphenylmethylamino - penicillanate with 50% trifluoroacetic acid in dichloromethane, resulted in the cleavage of triphenylmethyl group and one tert-butyl group. While the removal of both triphenylmethyl groups as well as di-tert-butylamino carbonyl group occurred when 75% trifluoroacetic acid was used. The significance of this study is to synthesize β-lactam derivatives that might to be more resistant to degradation by β-lactamase and hence, therapeutically more effective. |
| format | Article |
| id | doaj-art-4af74e204ed84d2f8199ff0386dc78cb |
| institution | Kabale University |
| issn | 1727-2114 2311-8865 |
| language | English |
| publishDate | 2012-11-01 |
| publisher | An-Najah National University |
| record_format | Article |
| series | مجلة جامعة النجاح للأبحاث العلوم الطبيعية |
| spelling | doaj-art-4af74e204ed84d2f8199ff0386dc78cb2025-08-20T03:44:03ZengAn-Najah National Universityمجلة جامعة النجاح للأبحاث العلوم الطبيعية1727-21142311-88652012-11-01271536810.35552/anujr.a.27.1.7Synthesis of Selective β-Lactam DerivativesIyad Ali0Nina Sakhnini1Department of Medical Sciences, Faculty of Medicine and Health Sciences, An-Najah Na-tional University, Nablus, PalestineNoneIn this work, the mild conditions of Mitsunobu reaction were used to convert the hydroxyl group of 6-triphenylmethylaminopenicillanyl alcohol to amines by using different nuleophiles such as phthalimide, di-tert-butyliminodicarboxylate and potassium cyanate. The existence of the β-lactam carbonyl group increased the instability towards nucleophilic attack of refluxing methanol and the four-membered ring was opened. Treating 3-Di-tert-Butoxycarbonylaminomethyl-6-triphenylmethylamino - penicillanate with 50% trifluoroacetic acid in dichloromethane, resulted in the cleavage of triphenylmethyl group and one tert-butyl group. While the removal of both triphenylmethyl groups as well as di-tert-butylamino carbonyl group occurred when 75% trifluoroacetic acid was used. The significance of this study is to synthesize β-lactam derivatives that might to be more resistant to degradation by β-lactamase and hence, therapeutically more effective.https://journals.najah.edu/media/journals/full_texts/synthesis-selective-b-lactam-derivatives.pdf |
| spellingShingle | Iyad Ali Nina Sakhnini Synthesis of Selective β-Lactam Derivatives مجلة جامعة النجاح للأبحاث العلوم الطبيعية |
| title | Synthesis of Selective β-Lactam Derivatives |
| title_full | Synthesis of Selective β-Lactam Derivatives |
| title_fullStr | Synthesis of Selective β-Lactam Derivatives |
| title_full_unstemmed | Synthesis of Selective β-Lactam Derivatives |
| title_short | Synthesis of Selective β-Lactam Derivatives |
| title_sort | synthesis of selective β lactam derivatives |
| url | https://journals.najah.edu/media/journals/full_texts/synthesis-selective-b-lactam-derivatives.pdf |
| work_keys_str_mv | AT iyadali synthesisofselectiveblactamderivatives AT ninasakhnini synthesisofselectiveblactamderivatives |