Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents

Hamada H Amer; Omar M Ali; Akram A Salama; Marwa S El-gendy; Omima K Houssin

doi:10.5455/njppp.2018.8.0416408052018-1

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Original Research
Online Published: 27 Jun 2018

Natl J Physiol Pharm Pharmacol. 2018; 8(9): 1275-1286

doi: 10.5455/njppp.2018.8.0416408052018-1

Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents

Hamada H Amer, Omar M Ali, Akram A Salama, Marwa S El-gendy, Omima K Houssin.

Abstract
Background: 1,3,4-oxadiazoles square measure a very important category of heterocyclic compounds with a broad variety of biological activities such as medicament, analgesic, ulcerogenicity, apoptosis inducer, anti-mycobacterial, antifungal, antitumor, P-glycoprotein Inhibitors, pesticides, 4-hydroxylase inhibitors, and antiepileptic drug activity.

Aims and Objectives: The present study is undertaken to study the evaluation of new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents.

Materials and Methods: A sequence of acyclic nucleoside derivatives, arylidines, oxadiazole, and α-aminophosphonates derived from 1,3,4-oxadiazole moiety were synthesized, observed by thin-layer chromatography, and purified by crystallization and another chromatographic methods; then, the prepared compounds were confirmed chemically by spectroscopic analysis such as infrared, mass spectra, and1H nuclear magnetic resonance and also elucidated by elemental analysis.

Results: The synthesized compounds were tested for their anticancer activity by measuring the inhibitory activity against hepatocellular carcinoma cell method under conditions with 50% inhibitory concentration (IC50) = 38.8 ± 5.4 μg/ml, IC50 = 89.1 ± 7.6 μg/ml, IC50 = 25.4 ± 3.8 μg/ml, IC50 = 90.2. ± 8.1 μg/ml, IC50 = 86.9 ± 7.9 μg/ml, IC50 = 248 ± 19.6 μg/ml, and IC50 = 12.5 ± 4.7 μg/ml for compounds 3, 7a, 9a, 11d, 13b, 15e, and 16a, respectively. 5-fluorouracil was used as reference anticancer drug in this work.

Conclusion: The synthesized compounds 3 (hydrazide), 7a and 9a (acyclic nucleosides), 11d (arylidines derivative), 13b (oxadiazoline derivative), and 15e and 16a (α-aminophosphonate derivatives) show moderate-to-high activity against hepatocellular carcinoma cells.

Key words: α-aminophosphonates; Arylidines Derivatives; Oxadiazole; Anticancer Activity

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How to Cite this Article

Pubmed Style

Amer HH, Ali OM, Salama AA, El-gendy MS, Houssin OK. Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents. Natl J Physiol Pharm Pharmacol. 2018; 8(9): 1275-1286. doi:10.5455/njppp.2018.8.0416408052018-1

Web Style

Amer HH, Ali OM, Salama AA, El-gendy MS, Houssin OK. Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents. https://www.njppp.com/?mno=297787 [Access: June 26, 2026]. doi:10.5455/njppp.2018.8.0416408052018-1

AMA (American Medical Association) Style

Amer HH, Ali OM, Salama AA, El-gendy MS, Houssin OK. Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents. Natl J Physiol Pharm Pharmacol. 2018; 8(9): 1275-1286. doi:10.5455/njppp.2018.8.0416408052018-1

Vancouver/ICMJE Style

Amer HH, Ali OM, Salama AA, El-gendy MS, Houssin OK. Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents. Natl J Physiol Pharm Pharmacol. (2018), [cited June 26, 2026]; 8(9): 1275-1286. doi:10.5455/njppp.2018.8.0416408052018-1

Harvard Style

Amer, H. H., Ali, . O. M., Salama, . A. A., El-gendy, . M. S. & Houssin, . O. K. (2018) Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents. Natl J Physiol Pharm Pharmacol, 8 (9), 1275-1286. doi:10.5455/njppp.2018.8.0416408052018-1

Turabian Style

Amer, Hamada H, Omar M Ali, Akram A Salama, Marwa S El-gendy, and Omima K Houssin. 2018. Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents. National Journal of Physiology, Pharmacy and Pharmacology, 8 (9), 1275-1286. doi:10.5455/njppp.2018.8.0416408052018-1

Chicago Style

Amer, Hamada H, Omar M Ali, Akram A Salama, Marwa S El-gendy, and Omima K Houssin. "Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents." National Journal of Physiology, Pharmacy and Pharmacology 8 (2018), 1275-1286. doi:10.5455/njppp.2018.8.0416408052018-1

MLA (The Modern Language Association) Style

Amer, Hamada H, Omar M Ali, Akram A Salama, Marwa S El-gendy, and Omima K Houssin. "Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents." National Journal of Physiology, Pharmacy and Pharmacology 8.9 (2018), 1275-1286. Print. doi:10.5455/njppp.2018.8.0416408052018-1

APA (American Psychological Association) Style

Amer, H. H., Ali, . O. M., Salama, . A. A., El-gendy, . M. S. & Houssin, . O. K. (2018) Synthesis of some new 1,3,4-oxadiazole derivatives bearing sugars and α-aminophosphonate derived from 4-nitrophenol as anticancer agents. National Journal of Physiology, Pharmacy and Pharmacology, 8 (9), 1275-1286. doi:10.5455/njppp.2018.8.0416408052018-1

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