Synthesis of novel 6-substituted-5,6-Dihydrobenzo[4,5] Imidazo[1,2-c] quinazoline compounds and evaluation of their properties

Hiba Ali Hasan*, Emilia Abdulmalek, Tawfik A. Saleh, Mohd Basyaruddin Abdul Rahman, Khozirah Binti Shaari, Bohari Mohd Yamin, Kim Wei Chan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

New 6-substituted-5,6-dihydrobenzo[4,5] imidazo[1,2-c] quinazoline compounds were synthesized using two different protocols: microwave-enhanced and classical heating methods. A comparison study that was set up to compare both the methods and the results showed that the microwave-assisted method produced a better percentage yield (up to 98%) in a very short reaction time (only a few minutes). All compounds were characterized by spectroscopic and elemental analysis. Only one compound was analyzed by single crystal X-ray diffraction despite the difficulties of getting good crystal even after several attempts. The X-ray crystallography results were chemically acceptable and confirmed the structure of benzimidazoquinazoline 5. Incidentally, the studied derivatives were found to emit a very nice blue light when exposed to UV-light. Therefore, a photoluminescence study was performed as a part of the characterization processes. Biological application as an antimicrobial and an antioxidant for the target analogues was performed. Some derivatives exhibited high antibacterial activity against studied Gram-positive strains, although they were not active against Gram-negative strains. Moreover, some of them showed excellent antioxidant activities against both of the studied antioxidant DPPH and ABTS•+ radicals.

Original languageEnglish
Pages (from-to)482-494
Number of pages13
JournalJournal of Molecular Structure
Volume1193
DOIs
StatePublished - 5 Oct 2019

Bibliographical note

Publisher Copyright:
© 2019 Elsevier B.V.

Keywords

  • Antimicrobial
  • Antioxidant
  • Dihydrobenzo[4,5]imidazo[1,2-c]quinazolin
  • Fluorescence
  • Single crystal

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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