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

Research output: Contribution to journalArticle

1 Citation (Scopus)

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
Publication statusPublished - 5 Oct 2019
Externally publishedYes

Fingerprint

Quinazolines
Antioxidants
Microwaves
Derivatives
Spectroscopic analysis
X ray crystallography
Ultraviolet radiation
Photoluminescence
Single crystals
Heating
X ray diffraction
Crystals
Chemical analysis

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

Cite this

Hasan, H. A., Abdulmalek, E., Saleh, T. A., Abdul Rahman, M. B., Shaari, K. B., Mohd. Yamin, B., & Chan, K. W. (2019). Synthesis of novel 6-substituted-5,6-Dihydrobenzo[4,5] Imidazo[1,2-c] quinazoline compounds and evaluation of their properties. Journal of Molecular Structure, 1193, 482-494. https://doi.org/10.1016/j.molstruc.2019.04.111

Synthesis of novel 6-substituted-5,6-Dihydrobenzo[4,5] Imidazo[1,2-c] quinazoline compounds and evaluation of their properties. / Hasan, Hiba Ali; Abdulmalek, Emilia; Saleh, Tawfik A.; Abdul Rahman, Mohd Basyaruddin; Shaari, Khozirah Binti; Mohd. Yamin, Bohari; Chan, Kim Wei.

In: Journal of Molecular Structure, Vol. 1193, 05.10.2019, p. 482-494.

Research output: Contribution to journalArticle

Hasan, Hiba Ali ; Abdulmalek, Emilia ; Saleh, Tawfik A. ; Abdul Rahman, Mohd Basyaruddin ; Shaari, Khozirah Binti ; Mohd. Yamin, Bohari ; Chan, Kim Wei. / Synthesis of novel 6-substituted-5,6-Dihydrobenzo[4,5] Imidazo[1,2-c] quinazoline compounds and evaluation of their properties. In: Journal of Molecular Structure. 2019 ; Vol. 1193. pp. 482-494.
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