Synthesis of Thioxoquinazolin-4(3H)-one Derivatives Under Microwave and Ultrasonic Irradiation with Classical Heating

Abstract

Quinazolinone derivatives have been reported to show a variety of biological properties, such as antimicrobial 1-6 , anticonvulsant 7-10 , antitumor 11-16 , anticoccidial 17 , antidepressant 18 , antihistaminic 19,20 , antiinflammatory 21-24 and antiviral 25,26 activities. Febrifugine and its analogue have been used as an anti malarial treatment 27-29. In addition, many thioxoquinazolin-4(3H)-one derivatives exhibit a considerable variety of activities, such as anticonvulsant 30 , anticancer 31,32 , antiulcer 33 and antiinflammatory and have been used as therapeutic agents for neuro-protection 34. Some novel thioxoquinazolinone derivatives have been synthesized using three different methods i.e., conventional synthesis, ultrasonic and microwave irradiation. The structures of these compounds were firmly established by well-defined IR, 1 H NMR, 13 C NMR, 2D NMR and ESI-MS spectroscopies. These compounds were then examined for antibacterial properties. EXPERIMENTAL The melting points (m.p.) were determined using an Electrothermal IA900 digital capillary melting point apparatus. The IR spectra were recorded in KBr discs on a Perkin Elmer 1000 FT-IR spectrophotometer (νmax in cm-1). The 1 H NMR, 13 C NMR spectra and 2D NMR spectra were collected in DMSO-d6 or (CDCl3) using a JEOL-ECP-400 and on Bruker 600 MHz spectrometer. The chemical shifts were reported as parts per million (δ ppm) and the coupling constants (J) are given in Hz,

Molecular docking and biological evaluation of some thioxoquinazolin-4(3H)-one derivatives as anticancer, antioxidant and anticonvulsant agents

“…Quinazoline derivatives 1 – 3 (Fig. 1 b) were synthesized according to the procedures reported previously by our group [ 31 , 32 ].…”

“…Quinazolinone derivatives were prepared according to the following literature procedures [ 31 , 32 ].…”

“…The quinazoline moiety containing compounds is of considerable medicinal importance because of their diverse biological activities. It has been observed that they possess anticancer [ 1 – 5 ], antibacterial [ 6 , 7 ], antifungal [ 7 , 8 ], antitubercular [ 9 , 10 ], antiviral [ 11 , 12 ], anticoccidial [ 13 , 14 ], anti-inflammatory and analgesics [ 15 – 21 ], antidepressant [ 22 – 24 ], anticonvulsant [ 23 , 24 ], antimalarial [ 25 , 26 ], antioxidant [ 27 ], antileishmanial [ 28 ], neuroprotective [ 29 ], antiobesity [ 30 ], antihypertensive [ 31 ], anti-H 1 -antihistaminic [ 32 ], and antiprotozoal activities [ 33 ]. The quinazoline moiety is a core unit in a variety of drugs such as Alfuzosin, Nolatrexed, CS 1101 (CAL 101), Balaglitazone, Milciclib, and Letermovir (Fig.…”

In vitro Antioxidant, Cytotoxicity Study on EAC Cell Line of Quinazolin-4(3H)-one Derivatives: Synthesis, Molecular Docking, in silico Drug Likeness

“…The quinazolin-4(3H)-one compounds are of extensive medicinal magnitude as of their assorted biological tricks. It have been experiential which exibits like antiviral, anticancer, antibacterial, antifungal, antitubercular, anticoccidial, 1 anti-inflammatory and analgesics, antidepressant, anticonvulsant, antimalarial, antioxidant, antileishmanial, 2 neuroprotectivie, 3 obesity, 4 antihypertensive, 5 anti-H1-antihistaminic, 6 and antiprotozoal activities. 7 The quinazoline candidate is a central part in array of drugs for instance Gefitinib, 8 Nolatrexed, 9 CS 1101 (CAL 101), 10,11 Erlotinib, 12 Milciclib, 13,14 and Lapatinib 15 (Figure 1a-b).…”

Ultrasonically Assisted N-Cyanoacylation and Synthesis of Alkyl(4-(3-cyano-4,6-dimethyl-2-oxopyridin-1(2H)-yl)benzoyl)amino Acid Ester Derivatives

“…Ultrasonication is now considered an important tool to perform organic reactions; in addition, it is a cost-effective method to support numerous reactions that offer a facile, clean, green, and eco-friendly way for the synthesis of compounds with biological values . Moreover, this process offers more advantages over the conventional heating method in terms of reaction rate and time. − …”