Synthesis and Antimicrobial Activities of Novel Quinazolinone Acylhydrazone Derivatives Containing the Indole Moiety

Abstract

A series of novel quinazolinone acylhydrazone derivatives containing the indole moiety were designed, synthesized, and evaluated for their inhibition activities against some important phytopathogens in vitro. Antibacterial experiments indicated that some compounds exhibited remarkable inhibition activities against tested bacteria. Especially, the EC50 values of 7a (EC50 = 55.13 μg/mL against Xoo, EC50 = 56.92 μg/mL against Rs) demonstrated the best antibacterial activities against Xoo and Rs than the other compounds, and the control agents Bismerthiazol (EC50 = 89.80 μg/mL against Xoo) and Thiodiazole copper (EC50 = 189.52 μg/mL against Rs), moreover, compound 7o (EC50 = 50.80 μg/mL) displayed the excellent activity against Xac than the control Bismerthiazol (EC50 = 56.92 μg/mL).

Novel 3-Thioether-4-indolimino-4H-1,2,4-triazole Derivatives Bearing Pyridyl Moiety: Design, Synthesis and Bioactivity Evaluation in vitro

“…1,2-Substituted-1H-indole-3-carbaldehydes (8 and 10～ 11) were prepared according to literature procedures. [29,24,30] The physical and spectral data of the prepared compounds 8 and 10～11 were consistent with those in the literature [29,24,30] .…”

“…[6] The amino and mercapto groups are ready-made nucleophilic centers for the preparation of fused heterocyclic rings. [21] Noteworthily, our previous work led to the discovery of a series of novel substituted indole derivatives possessing excellent antitumor activities, such as compounds 4, [22] 5 [23] (Figure 1) and antimicrobial activities [24] such as compound 6 [25] (Figure 1). Moreover, there are also many drugs containing indole moiety for tumor treatment, such as nintedanib, vinblastine, vinorelbine, sunitinib, melatonin, indirubin, etc.…”

Indole/isatin‐containing hybrids as potential antibacterial agents

“…Some indole–quinazoline/quinazolinone hybrids also demonstrated a considerable antibacterial activity, and among them, hybrid 88 (EC 50 : 50.80 μg/ml) displayed the higher activity against Xac than the reference bismerthiazol (EC 50 : 56.92 μg/ml). [ 184,185 ]…”

Design, Synthesis, and Structure–Activity Relationship of Quinazolinone Derivatives as Potential Fungicides

“…The 4(3H)-quinazolinone skeleton belongs to the Ncontaining heterocyclic building block and is composed of a benzene ring and a pyrimidine ring, 10 This skeleton is widely present in natural products, including luotonin A, 11 tryptan-thrin, 12 evodiamine, 13 rutaecarpine, 14 quinazolinone, and 2methylquinazolinone (Figure 1). Its derivatives display various pharmacological properties, such as antifungal, 15 antibacterial, 16 antimalarial, 17 anticancer, 18 and antiviral 19 activities. In addition, the backbone of 4(3H)-quinazolinone is also critical for the prevention and treatment of agricultural diseases; commercial fungicides fluquinconazole and proquinazid are two representative drugs (Figure 1).…”