Anti-inflammatory, antibacterial and molecular docking studies of novel spiro-piperidine quinazolinone derivatives

Abstract

A series of novel substituted quinazolinone derivatives was synthesized and characterized by 1 H NMR and LC-MS spectral techniques. The overall results of the antibacterial tests showed that these compounds had better bacteriostatic activity against Grampositive bacteria than their parent compounds. Furthermore, compounds 5f, 6b and 6f showed potent activity against Enterococcus faecalis (ATCC 51299), with MIC values <0.2 g/mL. Compounds 4e, 5g, 5e and 6c showed excellent activity, with MIC values <0.4 g/mL. Gram-negative bacteria Escherichia coli (ATCC 35218) and Klebsiella (ATCC 700603) are more resistant to lower concentrations of the synthesized compounds. The anti-inflammatory activities of the synthesized compounds were evaluated using the Carrageenan-induced rat Paw oedema method and ibuprofen as a standard drug. Compounds 4a and 4b exhibited good activity. Additionally, docking stimulations were performed to position compounds 4e, 4g, 5e, 5f, 6a and 6f into the EGFR kinase domain and human oestrogen receptor active site to determine probable binding information. This study indicated that compounds 6a and 6f have significant binding activities of 58.36 and 57.67 kJ mol −1 , respectively.

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“…Benzyl substitution at 2 nd position has remarkable anti-Leishmanial properties. [44] Substitution on 3 rd position-R 2 N-Phenyl with ortho, para, or meta substitution increases the activity. However, benzyl group is essential for antibacterial activity.…”

Green chemistry approach to the synthesis of 3-substituted-quinazolin-4(3H)-ones and 2-methyl-3-substituted-quinazolin-4(3H)-ones and biological evaluation

“…Quinazolinones are a group of heterocyclic compounds exhibiting a range of significant biological and pharmacological activities. Their structural diversity greatly affects their biological activity and they are proven to possess antitubercular (1,2), antibacterial (3,4), antitumor (5,6), anticonvulsant (7,8), anti-inflammatory (9,10) and antiviral (11) activities (Figure 1).…”

Spectrophotometric Determination of Paracetamol using a Newly Synthesized Chromogenic Reagent 4-[(2-amino-1, 3thiazol-4-yl)amino]nitro benzene

“…Enhanced lipid solubility with hydrophilicity [10]. Thiazole is widely used as anti-inflammatory drugs [11], sulfathiazole as the antimicrobial agent [12,13], penicillin that has a thiazole ring in their structure as Antibiotics [14], Antioxidant [15], Antiviral like Ritonavir drug [16], and anti-cancer properties [17,18]. They are also used in the treatment of Alzheimers disease, hypertension [19], Anti-allergies [20], cytotoxicity [21], and Anti-HIV [22].…”