A convenient synthesis, reactions and biological evaluation of novel pyrazolo[3,4- b ]selenolo[3,2- e ]pyrazine heterocy
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02635-z
ORIGINAL RESEARCH
A convenient synthesis, reactions and biological evaluation of novel pyrazolo[3,4-b]selenolo[3,2-e]pyrazine heterocycles as potential anticancer and antimicrobial agents Remon M. Zaki
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Mokhtar A. Abdul-Malik1,2 Saber H. Saber3 Shaban M. Radwan1 Adel M. Kamal El-Dean1 ●
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Received: 8 June 2020 / Accepted: 8 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract A novel series of 5-amino-6-substituted-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]selenolo[3,2-e]pyrazines (3a–e) was synthesized by the reaction of the chloro pyrazolo[3,4-b]pyrazine carbonitrile 1 with selenium element in the presence of sodium borohydride and ethanol, followed by the reaction with α-halo alkylating agents to produce the selanyl-alkylated derivatives 2a–e. The latter compounds underwent Thorpe-Ziegler cyclization upon heating with ethanolic sodium ethoxide solution to afford the target selenolopyrazolopyrazine compounds. The 5-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b] selenolo[3,2-e]pyrazine-6-carboxamide (3b) was used as a versatile precursor for synthesis of new heterocyclic fused to the pyrazoloselenolopyrazine moiety namely: pyrimidine and imidazopyrimidine. Assignment of the chemical structures for the newly synthesized compounds was confirmed on the bases of elemental and spectral techniques including FT-IR, 1H NMR, 13 C NMR, and mass spectra. Furthermore, certain compounds were screened for their antimicrobial activity which revealed remarkable activities against various pathogenic strains of bacteria and fungi. Alternatively, some of these compounds exhibited promising anticancer action against some colon and breast cancer cells. Graphical Abstract
Keywords Pyrazoloselenolopyrazine Pyrimidine Synthesis Reactions Antimicrobial Anticancer activity ●
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Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02635-z) contains supplementary material, which is available to authorized users. * Remon M. Zaki [email protected] 1
Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt
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Chemistry Department, Faculty of Science, Taiz University, Taiz, Yemen
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Zoology Department, Faculty of Science, Assiut University, Assiut 71516, Egypt
Medicinal Chemistry Research
Introduction Pyrazolo[3,4-b]pyrazine ring system is a privileged fundamental scaffold in heterocyclic chemistry. Molecules embedded with these scaffolds are central pharmaceutical intermediates in medicinal chemistry and have enlarged distinctive attention because of their broad spectrum of pharmacological properties. Many pyrazolopyrazines are considered as anticancer [1], antioxidant [2], anticonvulsant [3], antiparasitic [4], bone metabolism improvers [5], blood platelet aggregation [6], antibacterial and antifungal agents [7, 8] as well as exhibiting antiinflammatory and analgesic activities [9]. Certain pyrazolo[3,4-b]p
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