Syntheses and in silico pharmacokinetic predictions of glycosylhydrazinyl-pyrazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]triazolo[4,3-a]pyrimidines as anti-proliferative agents
Journal Article
·
· Medicinal Chemistry Research (Print)
- Alexandria University, Chemistry Department, Faculty of Science (Egypt)
- The Ministry of Education (Yemen)
- Kafrelsheikh University, Pharmaceutical Chemistry Department, Faculty of Pharmacy (Egypt)
New glycosylhydrazinyl-pyrazolo[1,5-c]pyrimidines were synthesized by the reaction of respective 5-aryl-7-hydrazino-2-phenylpyrazolo[1,5-c]pyrimidines (1a-d) with glucose, galactose, and xylose in ethanol. Their glycopyranosyl structures were reasoned to be in chair conformations and each have hydrazine moiety in the β-configuration. Also, pyrazolo[1,5-c]triazolo[4,3-a]pyrimidines derivatives were synthesized by the reaction of 1a-d with benzoic acid in the presence of phosphorousoxy chloride or by the reaction with benzaldehyde derivatives followed by cyclization in the presence of bromine. All structures of the compounds were confirmed from their IR, {sup 1}H, {sup 13}C, DPET-135°, {sup 1}H-{sup 1}H COSY, {sup 1}H-{sup 13}C HMQC, {sup 13}C-{sup 1}H HMBC spectra and microanalysis. The synthesized compounds showed inhibition of proliferation of MCF-7 human breast cancer cells with IC{sub 50} values ranging from 0.56 to 8.86 µg/ml. Some of the most active compounds showed acceptable predicted pharmacokinetics and drug-likeness properties. .
- OSTI ID:
- 22936212
- Journal Information:
- Medicinal Chemistry Research (Print), Journal Name: Medicinal Chemistry Research (Print) Journal Issue: 2 Vol. 28; ISSN 1054-2523
- Country of Publication:
- United States
- Language:
- English
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