Synthesis and anticonvulsant activity of 2‐aryl‐3,4‐dialkyltetrahydro‐1,3,4‐oxadiazines and 2‐aryl‐3,4‐dialkyltetrahydro‐1,3,4‐oxadiazin‐5‐ones

Abstract

Several 2‐aryl‐3,4‐dialkyltetrahydro‐1,3,4‐oxadiazines have been synthesized from 2‐(1,2‐dialkylhydrazino)ethanol (2) and aromatic aldehydes. Also, three 2‐aryl‐3,4‐dialkyltetrahydro‐1,3,4‐oxadiazin‐5‐ones were obtained from the reaction of 1,2‐dialkylglycolylhydrazine (5) and aromatic aldehydes. These compounds exhibited activity in the maximal electroshock seizure test.

Pyrimidooxadiazine and triazolopyrimidooxadiazine derivatives: Synthesis and cytotoxic evaluation in human cancer cell lines

“…7 Chloro 1,5 dimethyl 3 phenyl 1H pyrimido [4,5 e] [1,3,4]oxadiazine (III) was prepared by the reaction of 5 bromo 2 chloro 6 methyl 4 (1 meth ylhydrazino)pyrimidine (II) with benzoyl chloride in the presence of K 2 CO 3 according to previous published method [13]. Subsequent treatment of compound (III) with pyrrolidine in boiling ethanol led to the replace ment of chorine atom to give 1,5 dimethyl 3 phenyl 7 (pyrrolidin 1 yl) 1H pyrimido [4,5 e] [1,3,4]oxadiaz ine (IV).…”

“…There are some reports in the litera ture on their cardiovascular, antibacterial, insecticidal, and anticonvulsive activities [2,3]. In addition, oxadi azines are useful intermediates in the synthesis of tenidap prodrugs or β lactam antibiotics, particularly, the synthesis of carbapenems and penems [4,5].…”

“…All synthesized compounds inhibited the growth of malignant cells in a dose dependent manner, but among them 1,5,7 trimethyl 3 phenyl 1H [1,2,4]triazolo[4',3':1,2]pyrimido[4,5 e][1,3,4]oxadiazine and [(1,5 dimethyl 3 phenyl 1H [1,2,4]triazolo[4',3':1,2]pyrimido[4,5 e] [1,3,4]oxadiazin 7 yl)sulfa nyl]acetonitrile, both with triazole moiety, were found to be more effective than other compounds; they also induced a sub G1 peak in the flow cytometry histogram of treated cells compared to controls, indicat ing that apoptotic cell death is involved in toxicity they induce. The results showed that compounds with triazole moiety fused to pyrimido[4,5 e] [1,3,4]oxadiazine derivatives are more active than those bearing chlorine or pyrrolidine groups at C 7 position.…”

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In vitro antiproliferative activities of some pyrimido [4,5 e] [1,3,4]oxadiazine and [1,2,4]triaz olo[4',3':1,2]pyrimido[4,5 e][1,3,4]oxadiazine derivatives were examined in human malignant cancer cell lines. All synthesized compounds inhibited the growth of malignant cells in a dose dependent manner, but among them 1,5,7 trimethyl 3 phenyl 1H [1,2,4]triazolo[4',3':1,2]pyrimido[4,5 e][1,3,4]oxadiazine and [(1,5 dimethyl 3 phenyl 1H [1,2,4]triazolo[4',3':1,2]pyrimido[4,5 e] [1,3,4]oxadiazin 7 yl)sulfa nyl]acetonitrile, both with triazole moiety, were found to be more effective than other compounds; they also induced a sub G1 peak in the flow cytometry histogram of treated cells compared to controls, indicat ing that apoptotic cell death is involved in toxicity they induce.

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Synthesis and antibacterial evaluations of new pyridazino[4,3‐e][1,3,4]oxadiazines

“…They have a diverse biological properties [1] such as inhibitors of bacterial growth [2], antimicrobial agents [2,3], and also useful intermediates in the synthesis of tenidap prodrugs or b-lactam antibiotics, especially, in the synthesis of carbapenems and penems [4,5], cardiovascular antibacterial, miticidal, nematocidal, acricidal, insecticidal, and anticonvulsive activities [6,7].…”