Synthesis and in vitro cytotoxicity studies of novel triazolo[4,3-b]pyridazinones

Abstract

New triazolo [4,3-b]pyridazinones were synthesized and evaluated for their potential in vitro cytotoxic antitumor properties. The compounds were prepared by 1,3-dipolar cycloaddition of pyridazin-3-ones with N-aryl-C-ethoxycarbonylnitrile imines, generated in situ from ethylhydrazono--bromoglyoxylates. The peri-and regioselectivity of the reaction were ascertained by 1 H and 13 C NMR spectroscopy of the cycloadducts.

Anti‐HAV Activity of Some Newly Synthesized Triazolo[4,3‐b]pyridazines

“…Chemistry 6-Phenyl- [1,2,4]triazolo [4,3-b]pyridazine-3(2H)-thione 2, as key compound for this study and for further syntheses of other fused heterocyclic compounds, was previously synthesized by Gafitanu et al [20] through the reaction of (6-phenylpyridazin-3-yl)-hydrazine 1 [21] with phenyl isothiocyanate. Here, we prepared compound 2 via the reaction of compound 1 with carbon disulfide in dry pyridine.…”

“…In the last few decades, the chemistry of triazolo [4,3-b]pyridazine derivatives has received considerable attention owing to their variety of biological activities, especially as a potential antiviral [1], antitumoral [2,3], sedative/hypnotic [4], anti-anxiety [5 -7], adenine receptor ligand [8,9], hypotensive and heart rate activity [10], as herbicidal, pesticidal [11], and bactericidal [12]. In connection with our research program for the synthesis of different fused heterocyclic compounds with antiviral [1,13,14] and antimicrobial interest [15 -19], we describe the syntheses of some triazolo [4,3-b]pyridazine derivatives with promising anti-HAV activity.…”

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6-Phenyl- [1,2,4]triazolo [4,3-b]pyridazine-3(2H)-thione 2 was used as precursor for the preparation of some novel 3-S-substituted-6-phenyl- ,4]oxadiazole derivatives 15 and 17, are described. Some of the prepared products revealed a promising antiviral activity against hepatitis-A virus (HAV, MBB-cell culture adapted strain).

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Synthesis and in‐vitro Cytotoxic Evaluation of Novel Pyridazin‐4‐one Derivatives

“…Recently, we have reported the synthesis and the cytotoxicity activities of new triazolopyridazinone derivatives. Some of these compounds exhibited significant cytotoxicity against the Hep cell line [12]. In continuation of our studies [12,13] on the synthesis of new pyridazinone compounds, herein, we report the synthesis of some potent analogs of N-substituted-pyridazinone derivatives, which have been tested for their antitumor activity.…”

A brief review on Triazin-pyridazinones: Synthesis and biological activities

“…The compound 24 was more cytotoxic than compound 23. Compound 24 exhibited significant cytotoxicity against the Hep cell line [31]. Synthesis: The preparation of some derivatives of the [1,2,4]triazolo [4,3-b]pyridazine system from ethyl N-benzoyl-(6-chloro [1,2,4]triazolo [4,3-b]pyridazin-3-yl)glycinate is reported [32].…”