Synthesis of some substituted furo[3,2-g]chromeno[2,3-c]pyrazole and pyrazoline derivatives from 5-hydroxybergapten and 5-hydroxyisopimpinellin as EGFR and VEGFR-2 kinase inhibitors
- Authors: Amr A.E.1,2, Abdalla M.M.3, Essaouy S.A.4, Areef M.M.4, Elgamal M.H.2, Nassear T.A.4, Haschich A.E.4
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Affiliations:
- Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy
- Applied Organic Chemistry Department
- Research Unit
- Organic Chemistry Department, Faculty of Science
- Issue: Vol 87, No 7 (2017)
- Pages: 1601-1609
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/220837
- DOI: https://doi.org/10.1134/S1070363217070258
- ID: 220837
Cite item
Abstract
A series of substituted 7H-furo[3,2-g]chromen-7-one and furo[3,2-g]chromeno[2,3-c]pyrazole derivatives (2–9) were synthesized by using 5-hydroxy-4-methoxy-7H-furo[3,2-g]chromen-7-one (5-hydroxybergapten) and 5-hydroxy-4,9-dimethoxy-7H-furo[3,2-g]chromen-7-one (5-hydroxyisopimpinellin) (1) as starting materials. Compound 1 reacted with amino acid esters to give the corresponding 5-N-amino acid derivatives 2 and 3, respectively. Bromination of 1 gave the corresponding 6-bromo analouges 4, that were treated with amino acids esters to give the corresponding 6-N-amino acids analogues 5. Treatment of the later with hydrazine hydrate led to cleavage of the pyran ring and gave the corresponding pyrazoline benzofuran derivatives 6. Formylation of 1 gave aldehyde derivative 7, which was condensed with amino acid to give the corresponding 5-N-amino-6-formyl derivatives 8. Cyclization of compounds 8 with hydrazine hydrate gave the corresponding pyrazoline derivatives 9. All synthesized compounds were tested as EGFR and VEGFR-2 kinase inhibitors.
About the authors
A. E. Amr
Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC), College of Pharmacy; Applied Organic Chemistry Department
Email: mmostafa201120@yahoo.com
Saudi Arabia, Riyadh, 11451; Dokki, Cairo, 12622
M. M. Abdalla
Research Unit
Author for correspondence.
Email: mmostafa201120@yahoo.com
Egypt, 6th October City
S. A. Essaouy
Organic Chemistry Department, Faculty of Science
Email: mmostafa201120@yahoo.com
Egypt, Banha
M. M. H. Areef
Organic Chemistry Department, Faculty of Science
Email: mmostafa201120@yahoo.com
Egypt, Banha
M. H. Elgamal
Applied Organic Chemistry Department
Email: mmostafa201120@yahoo.com
Egypt, Dokki, Cairo, 12622
T. A. Nassear
Organic Chemistry Department, Faculty of Science
Email: mmostafa201120@yahoo.com
Egypt, Banha
A. E. Haschich
Organic Chemistry Department, Faculty of Science
Email: mmostafa201120@yahoo.com
Egypt, Banha
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