Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c] [1,3,2]diazaphosphole-2-oxides

Abstract

Some novel 2-(heterylcarboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo [3,4-c][1,3,2]diazaphosphole-2-oxides (4-13) have been synthesized from reaction of 3,4-diamino-1,2,5-oxadiazole (3) with various dichlorophosphinylcarboxamides (2), which were prepared by C-acylation of electron-rich heterocyclic compounds with dichloro isocyanato phosphine oxide (Kirsanov isocyanate) (1) in dry octane, in the presence of triethylamine at 50-60 °C. Their structures were determined by IR, 1 H, 13 C, 31 P NMR and mass spectral (MS) studies. They were screened for antifungal and antibacterial activity against Curvularia lunata / Aspergillus niger and Staphylococcus aureus / Escherichia coli, respectively. Most of these compounds exhibited moderate activity in the assays.

Furazans in Medicinal Chemistry

“…The prominence of antibiotic resistance and the estimated global burden of multidrug resistant pathogens has prompted research efforts to identify novel chemotypes. Furazan derivatives are known to exhibit a range of antimicrobial activities, including antibiotic, antifungal, and antipest, − yet evidence of selectivity over eukaryotic cells is seldom provided. A report from Abbot Laboratories identified furazanopyrazines (Figure , compound 95 ) as broad-spectrum antibiotics with good selectivity over eukaryotic cell lines; antibiotic activity was observed in H. influenzae , S. aureus , and S. pneumoniae with no observable cytotoxicity in yeast ( C. albicans ) or human lymphocytes (Table ).…”

A mild and efficient synthesis of aminofurazans

“…Molecules containing furazan rings play a significant role in pharmaceutical science, showing more than 40 types of activity, including anticonvulsant, 8 anti-histamine, 7 anti-inflammatory, 9 anti-microbial, 10 antiplasmodial, 11 anti-HIV, 12 antifungal, 13 antitumor, 14 cardiovascular, 15 anti-Alzheimer's 16 activity and others. This structural unit is a part of many agro-chemicals, 17 and in most cases aminofurazans are key building blocks in their synthesis.…”

First Example of Catalytic Synthesis of Difurazanohexahydrohexaazapyrenes and in Vitro Study of Their Antitumor Activity

“…4,5 Aforesaid studies have contributed to the development of methods for the synthesis of furazanopyrazines 6−9 and have stimulated investigations into their physical 10 and biological 11,12 properties. Heterocycles containing an oxadiazole moiety possess antiatherogenic, 13 antimalarial, 14 and antimicrobial 15,16 activities, as well as neuroprotective 17 and antiproliferative 18 effects.…”

“…According to ref , the furazan ring constitutes a part of high energy materials, while the polynitrogenous derivatives of furazanopyrazine have been proposed for use as explosives. , Aforesaid studies have contributed to the development of methods for the synthesis of furazanopyrazines − and have stimulated investigations into their physical and biological , properties. Heterocycles containing an oxadiazole moiety possess antiatherogenic, antimalarial, and antimicrobial , activities, as well as neuroprotective and antiproliferative effects.…”