Application of the Cleavable Isocyanide in Efficient Approach to Pyroglutamic Acid Analogues with Potential Biological Activity
- Authors: Jassem A.M.1, Al-Ajely H.M.2, Almashal F.A.1, Chen B.3
-
Affiliations:
- College of Education for Pure Sciences, Department of Chemistry
- College of Science, Department of Chemistry
- Department of Chemistry
- Issue: Vol 89, No 12 (2019)
- Pages: 2562-2570
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/223249
- DOI: https://doi.org/10.1134/S1070363219120363
- ID: 223249
Cite item
Abstract
Two efficient procedures have been developed for the synthesis of pyroglutamic acid analogues 28, 29, and 34. According to the first method the Ugi (4C3C) reaction is followed by a post-transformation reaction, and the second method involves the Michael addition reaction. The present methodologies demonstrate the applicability of 1-(2,2-dimethoxyethyl)-2-isocyanobenzene (15) as a cleavable isocyanide in the Ugi/ post-transformation reaction and a strong nucleophile in the Michael addition reaction. The framework of pyroglutamic acid analogues has been constructed by the selective cleavage of the C-terminal amide bond and nucleophilic addition to the activated α,β-unsaturated carbonyl group.
About the authors
A. M. Jassem
College of Education for Pure Sciences, Department of Chemistry
Author for correspondence.
Email: ahmed.majedd@uobasrah.edu.iq
Iraq, Basrah, 61004
H. M. Al-Ajely
College of Science, Department of Chemistry
Email: ahmed.majedd@uobasrah.edu.iq
Iraq, Mosul, 41002
F. A. K. Almashal
College of Education for Pure Sciences, Department of Chemistry
Email: ahmed.majedd@uobasrah.edu.iq
Iraq, Basrah, 61004
B. Chen
Department of Chemistry
Email: ahmed.majedd@uobasrah.edu.iq
United Kingdom, Sheffield, S3 7HF
![](/img/style/loading.gif)