Studies on biologically active halogenated compounds. 1. Synthesis and central nervous system depressant activity of 2-(fluoromethyl)-3-aryl-4(3H)-quinazolinone derivatives

Abstract

Some 2-(fluoromethyl) analogues of 2-methyl-3-aryl-4-(3H)-quinazolinones have been synthesized and screened for CNS activities. It was shown that the 2-(fluoromethyl) analogues possess in general more potent CNS depressant activities and less toxicities than their parent compounds. Of particular interest were the 2-(fluoromethyl) analogues (22, 24, and 31) of methaqualone and 6-aminomethaqualone. Compound 24 was more potent in CNS depressant activity and less toxic than methaqualone. Compound 31 exhbited potent central muscle relaxing activity and markedly reduced toxicity as compared with 6-aminomethaqualone.

Methyl 2-[2-(benzyloxycarbonylamino)propan-2-yl]-5-hydroxy-6-methoxypyrimidine-4-carboxylate

“…Afloqualone has been evaluated as a successful anti-inflammatory agent with lower-back-pain patients (Tani et al, 1979). In view of the importance of pyrimidine derivatives, the title compound (I) was synthesized and its crystal structure was reported.…”

“…For hydrogenbond motifs, see: Bernstein et al (1995). For background to and applications of pyrimidine derivatives, see : Cheng & Roth (1971); Cox (1968); Eussell (1945); Jain et al (2006); Shinogi (1959); Tani et al (1979).…”

Synthesis of new 4(3H)-quinazolinone derivatives under solvent-free conditions using PEG-400

“…21 The latter on treatment with m-anisidine in refluxing pyridine for 5-6 h, followed by simple processing resulted in the formation of 2-(chloromethyl)-3-(3-methoxyphenyl) quinazolin-4(3H)-one 3a 22 (i.e.3a, Ar = C 6 H 4 -3-OCH 3 ). Conversion of 3 to corresponding 4, 5, and 6 derivatives is favored in presence of KI.…”

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

“…Many studies have been shown that compounds containing the pyrimidine ring possess antidiabetic, antibacterial, antifungal, antimalarial, and anticonvulsant activities, [12][13][14][15][16] and anticancer activities, [17,18] and many of pyrimidine compounds were reported to act as calcium channel blockers, [19] and as potential central nervous system (CNS) depressants. [20,21] Also, Pyrazoline derivatives widely occur in the environment, in the form of alkaloids, vitamins and pigments as constituents of plant and animal cell. Considerable attention has been carried out on the pyrazolines and substituted pyrazolines due to their inspiring biological activities such as antibacterial, antifungal, [22][23][24] antidepressant, [25][26][27][28] anticonvulsant, [29] and antitumor, [30] properties.…”