Synthesis and Bioactivity of Novel Bis‐heterocyclic Compounds Containing Pyrazole and Oxadiazoline

Abstract

Nucleophilic addition of the starting material 3-aryl-1-phenyl-4-formylpyrazoles (1~3) and 4-substituted aryloxyacetyl hydrazine (4a~4e) afford hydrazone compounds containg pyrazolyl (5a~5e, 6a~6e, 7a~7e) in the ethanol. These adducts were refluxed in Ac 2 O and furnished a series of novel bis-heterocyclic compounds. (8a~8e, 9a~9e, 10a~10e) via cyclic reaction. The structures of all newly synthesized compounds were established by IR, 1 H NMR, MS and elemental analysis. New compounds conducted preliminary tests of antibacterial activities about Fusarium oxyaporium, Verticillium dahliae, Rhizoctonia solani, Pychium aphanidermatum, Alternaria solani, Sclerotinia sclerotiorum. The results showed that the inhibiting rate of the bis-heterocyclic compounds (8a~8e, 9a~9e, 10a~10e) was higher than the pyrazolyl hydrazones (5a~5e, 6a~6e, 7a~7e) obviously.

Synthesis, insecticidal activities and structure–activity relationship studies of novel anthranilic diamides containing pyridylpyrazole‐4‐carboxamide

“…Notably, anthranilic diamides containing a 1‐(2‐pyridyl)pyrazole‐5‐ylcarbonyl moiety in the second section (B) show significantly better activity than other heterocyclic derivatives . In the literature, 1‐(2‐phenyl)pyrazole derivatives function as antitumour screening, and demonstrate potent antimicrobial activity …”

“…8 -10 In the literature, 11 derivatives function as antitumour screening, and demonstrate potent antimicrobial activity. 5,12 Encouraged by these reports, we propose an idea to examine whether the cyclisation of the anthraniloyl skeleton by an aromatic acyl moiety (B) could have an effect on potential insecticidal activities. Based on the molecular structure of anthranilic diamide, we changed the substituted position of carboxamide on the pyrazole ring from 5 to 4.…”

Antimicrobial and antiprotozoal activity of 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines: a review

“…28) Fluconazole, used as reference substance, displayed activity below ≤1 µg/ml (Kumar et al 2010). Yang et al (2011) conducted a series of reactions and obtained 15 bis-heterocyclic compounds containing pyrazole and 1,3,4-oxadiazoline scaffold. Antifungal activity was assessed against five species of fungi: Fusarium oxysporum, Verticillium dahliae, Rhizoctonia solani, Pychium aphanidermatum, Alternaria solani and Sclerotinia sclerotiorum.…”

Synthesis and Evaluation of New Bis‐1,3,4,2‐triazaphospholinoalkane Derivatives as In Vitro α‐Amylase and Lipase Inhibitors

“…On the other hand, the chemistry of heterocycles is an integrating part of chemical sciences which represent a considerable part of modernity and form an important class of organic components. In recent years, several research works have been devoted to the synthesis of bis‐heterocyclic compounds because they have antioxidant, antitumor, anticancer, and antidepressants activities . Moreover, organophosphorus has received much attention due to their broad spectrum of biological activities such as antimicrobial, cytotoxic, and antiviral agents .…”