Synthesis of novel pyridazine derivatives as potential antimicrobial agents

Abstract

A series of novel pyridazine derivatives incorporated with triazole, thiazolidine, imidazolidine, oxazine, and quinazoline moieties was synthesized by the reaction of [6-(4-phenoxyphenyl)pyridazin-3-yloxy]acetyl isothiocyanate with variety of nucleophilic reagents. The structures of all products were confirmed and characterized by the elemental analysis and spectroscopic studies (IR, MS, 1 H NMR). Also, the products were investigated for their antibacterial and antifungal activities and were compared with the standard drugs. Most of the synthesized compounds demonstrated potent to weak antimicrobial activity.

Synthesis of Some Novel Thiazolo[3,2‐a]pyrimidine and Pyrimido[2,1‐b][1,3]thiazine Derivatives and their Antimicrobial Evaluation

“…Treatment of acid 1 (prepared from acylation of diphenyl ether by succinic anhydride under Fridel Crafts conditions [30]) with thiophen-2-carbaldehyde and thiourea in ethanol containing anhydrous potassium carbonate afforded 2-(2-mercapto-4-(4-phenoxyphenyl)-6-(thiophen-2-yl)-1,6-dihydropyrimidin-5-yl) acetic acid (2) (Scheme 1).…”

“…Compound 1 was prepared according to the published procedure [30]. Compound 1 was prepared according to the published procedure [30].…”

“…In addition, pyrimidine derivatives such as pyrazolo [1,5-a]pyrimidine, pyrido [2,3-d]pyrimidine, thieno [2,3-d]pyrimidines, pyrrolo [2,3-d]pyrimidines, and indolylpyrimidines showed potent antitumor [15][16][17][18][19][20], antitubercular [21], anti-inflammatory [22], and antidiabetic [23] activities. On the basis of the reported observations and in continuation of our ongoing interest in the synthesis of biologically active molecules [27][28][29][30], the present work describes the synthesis of new series of thiazolo [3,2-a]pyrimidine and pyrimido [2,1-b] [1,3] thiazine derivatives as well as the evaluation of their antibacterial and antifungal activities. On the basis of the reported observations and in continuation of our ongoing interest in the synthesis of biologically active molecules [27][28][29][30], the present work describes the synthesis of new series of thiazolo [3,2-a]pyrimidine and pyrimido [2,1-b] [1,3] thiazine derivatives as well as the evaluation of their antibacterial and antifungal activities.…”

Synthesis of Novel Phthalazine Derivatives as Potential Anticancer and Antioxidant Agents Based on 1‐Chloro‐4‐(4‐phenoxyphenyl)phthalazine

“…Acid 1 was prepared according to previously reported procedure via Friedel‐Crafts acylation of diphenyl ether with phthalic anhydride in tetrachloroethane in the presence of catalytic amount of anhydrous aluminum chloride. Hydrazinolysis of acid 1 with hydrazine hydrate in ethanol furnished 4‐(4‐phenoxyphenyl)phthalazin‐1(2H)‐one ( 2 ).…”

“…In view of the aforementioned facts and in continuation of our research interest for the synthesis of biologically active heterocycles , we report here the synthesis of novel series of phthalazine derivatives bearing tetrazole, triazole, imidazole, and triazine moieties, as well as an evaluation of their anticancer activities against four human tumor cell lines, namely, hepatocellular carcinoma HePG‐2, mammary gland breast cancer MCF‐7, human prostate cancer PC3, and colorectal carcinoma HCT‐116 using MTT assay. In addition, some of the synthesized compounds were investigated for their antioxidant activities.…”