Ionic liquid mediated four-component synthesis of novel phthalazinone based indole-pyran hybrids as cytotoxic agents

M. Shaheer Malik; Reem I. Alsantali; Meshari A. Alsharif; Sultan I. Aljayzani; Moataz Morad; Rabab S. Jassas; Munirah M. Al-Rooqi; Abdulrahman A. Alsimaree; Hatem M. Altass; Basim H. Asghar; Abdelrahman S. Khder; Saleh A. Ahmed

Arabian Journal of Chemistry (Feb 2022)

Ionic liquid mediated four-component synthesis of novel phthalazinone based indole-pyran hybrids as cytotoxic agents

M. Shaheer Malik,
Reem I. Alsantali,
Meshari A. Alsharif,
Sultan I. Aljayzani,
Moataz Morad,
Rabab S. Jassas,
Munirah M. Al-Rooqi,
Abdulrahman A. Alsimaree,
Hatem M. Altass,
Basim H. Asghar,
Abdelrahman S. Khder,
Saleh A. Ahmed

Affiliations

M. Shaheer Malik: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia; Corresponding authors at: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia
Reem I. Alsantali: Department of Pharmaceutical Chemistry, College of Pharmacy, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia
Meshari A. Alsharif: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia
Sultan I. Aljayzani: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia
Moataz Morad: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia
Rabab S. Jassas: Department of Chemistry, Jamoum University College, Umm Al-Qura University, 21955 Makkah, Saudi Arabia
Munirah M. Al-Rooqi: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia
Abdulrahman A. Alsimaree: Department of Basic Science (Chemistry), College of Science and Humanities, Shaqra University, Afif, Saudi Arabia
Hatem M. Altass: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia
Basim H. Asghar: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia
Abdelrahman S. Khder: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia; Faculty of Science, Chemistry Department, Mansoura University, 35516 Mansoura, Egypt
Saleh A. Ahmed: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia; Department of Chemistry, Faculty of Science, Assiut University, 71516 Assiut, Egypt; Corresponding authors at: Department of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah 21955, Saudi Arabia

Journal volume & issue: Vol. 15, no. 2
p. 103560

Abstract

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A robust design and synthesis of novel phthalazinone based indole-pyran hybrids as cytotoxic agents is described. A relatively safer ionic liquid medium ([BMIM]BF4) was utilized to mediate a one-pot, four-component reaction to access the novel hybrids in short reaction time and good yields. The cytotoxic potential of the hybrids was investigated against selected cancer cell lines. The hybrids 5h and 5b displayed potent activity with IC50 values in the range of 5.8–9.6 μM. The insilico docking demonstrated a pronounced affinity of hybrids 5h and 5b towards the human tankyrase-1 enzyme exhibiting binding energies values of −11.2 and −10.2 kcal/mole, respectively. Additional ADME and drug likeliness analyses revealed the potential of the active hybrids to be taken forward for advanced studies.

Published in Arabian Journal of Chemistry

ISSN: 1878-5352 (Print)
Publisher: Elsevier
Country of publisher: Netherlands
LCC subjects: Science: Chemistry
Website: http://www.journals.elsevier.com/arabian-journal-of-chemistry/

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