A Comparative Study of the in Vitro Bacteriostatic Action of Some Simple Derivatives of Furan, Thiophene, and Pyrrole

Abstract

A study of the in vitro bacteriostatic action of simple furan derivatives has demonstrated the value of the nitro group in the molecule for effective bacteriostasis of both gram-positive and gram-negative organisms, and the inactivity of analogous nonnitrated compounds (Dodd and Stilman, 1944). The proved function of the nitro group in the furan series created interest in its effect when introduced into other five-membered heterocyclic ring systems having a single hetero-atom. Thiophene and pyrrole, the sulfur and nitrogen analogues of furan, which have physical and chemical characteristics that reseinble furan in many respects, were chosen for a comparative study of the effect of a nitro group on the bacteriostatic action of such compounds. A series of simple thiophene and pyrrole derivatives both nitrated and nonnitrated was, therefore, prepared and tested for in vitro bacteriostatic action and the results were compared with corresponding furan derivatives. Certain furan derivatives having a substituent in the 2-position containg an aldehyde or ketone carbonyl group and nitrated in the 5-position are highly efficient bacteriostatic agents. The compounds 5-nitro-2-furaldehyde and 5nitro-2-acetofurone are excellent examples of active compounds of this type. The former and its semicarbazone derivative are two of the most active members of the furan series. The 2-acetyl derivatives of thiophene and pyrrole were prepared and compared with the active 2-acetyl furan derivatives. Nonnitrated and nitrated compounds are included for comparison. The effect of introducing a nitro group is clearly brought out. The data on bacteriostatic activity of 2-acetofurone semicarbazone and 5-nitro-2-acetofurone semicarbazone have not been published.

Nifuroxazide induces the apoptosis of human non‑small cell lung cancer cells through the endoplasmic reticulum stress PERK signaling pathway

“…The discovery of the therapeutic potential of nitrofuran derivatives dates back to 1948 when it was discovered how they induced antimicrobial activity (8). Nifuroxazide (NFZ), a gastrointestinal antibiotic, was first patented in 1961 (England), 1966 (France) and 1966 (USA) by Robert & Carrie Laboratories (9).…”

One-Electron Reduction Potentials: Calibration of Theoretical Protocols for Morita–Baylis–Hillman Nitroaromatic Compounds in Aprotic Media

“…Nitro compounds have been used against various diseases for over five decades [ 1 , 2 , 3 , 4 , 5 ] due to their wide range of pharmacological activity against bacteria [ 6 , 7 ], fungus [ 8 ], and tumors [ 9 , 10 ] as well as malaria, leishmaniasis, and Chagas disease [ 11 , 12 , 13 , 14 ]. The pharmacological mechanism of these compounds generally involves enzymatic bioreduction facilitated by the electron acceptor strength of the nitro group, leading to formation of free radicals with preferential toxicity for invading microorganisms [ 15 , 16 , 17 , 18 , 19 ].…”

Permeabilidade in vitro e in silico de análogos à nifuroxazida com atividade potencial frente a cepas multirresistentes de Staphylococcus aureus

“…Testes realizados com o furoato de 2-metila comprovaram que a substituição do grupo nitro na posição 5 do anel furânico por outros substituintes, como Cl, Br, CH 3 , CHO, CH 2 Cl e CH 2 OH, conferia inatividade frente a bactérias Gram-positivas e Gram-negativas, como Staphylococcus aureus e E. coli (WARD, DODD, 1948;DODD, CRAMER, WARD, 1950).…”