Synthesis, antibacterial evaluation, crystal structure and molecular interactions analysis of new 6-Bromo-2–chloro–3-butylquinazolin-4(3 H )-one

Oussama Ouerghi (1, 2) , Mohammed Geesi (3) , Abdellah Kaiba (1) , El Hassane Anouar (3) , Abdul-Malek S. Al-Tamimi (4) , Philippe Guionneau (5) , Elmutasim O. Ibnouf (6, 7) , Rachid Azzallou (8) , Md Afroz Bakht (3) , Yassine Riadi (4)

1 Department of Physics
2 UTM - Université de Tunis El Manar
3 Department of Chemistry
4 Department of Pharmaceutical Chemistry
5 ICMCB - Institut de Chimie de la Matière Condensée de Bordeaux
6 Department of Pharmaceutics
7 Department of Medical Microbiology
8 UH2MC - Université Hassan II [Casablanca]

An efficient process was described to prepare a novel 6‑bromo‑2‑chloro‑3-butylquinazolin-4(3H)-one. The targeted compound was synthesized from available chemicals and assessed for anti-bacterial activity. This new compound structure crystallises in the triclinic system with P-1 space group. Its unit cell parameters are (a = 4.91550(10) Å, b = 11.4764(2) Å, c = 12.1670(3) Å), volume (638.11(4) Å3), α= 110.079(8)°, β= 93.8130(10)°, γ = 95.4580(10)° and Z = 2. The crystal packing was stabilized by C = O…H hydrogen bonds and CH3CH2CH2CH2CHH….C π-stacking interaction and hydrogen π-π stacking interactions. Hirshfeld surfaces and their associated two-dimensional fingerprint plots were used to analyze the intermolecular interactions in the crystal structure. In addition, electrostatic surface potential (ESP) was generated using the density functional theory.

Mots clés: 6‑bromo‑2‑chloro‑3-butylquinazolin-4(3h)-one; Antibacterial; Crystal structure; Hirshfeld surface analysis

Domaines: Chimie thérapeutique; Cristallographie

Oussama Ouerghi, Mohammed Geesi, Abdellah Kaiba, El Hassane Anouar, Abdul-Malek S. Al-Tamimi, et al.. Synthesis, antibacterial evaluation, crystal structure and molecular interactions analysis of new 6-Bromo-2–chloro–3-butylquinazolin-4(3 H )-one. Journal of Molecular Structure, 2021, 1225, pp.129166. ⟨10.1016/j.molstruc.2020.129166⟩. ⟨hal-02929647⟩