preparation of sulfanilamide from benzene application
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Abstract
New amidine and benzene sulfonamide derivatives were developed and structures of the new products were confirmed by elemental and spectral analysis (FT-IR, ESI-MS, 1HNMR, and 13CNMR). In vitro, developed compounds were screened for their antibacterial and antifungal activities against medically important bacterial strains, namely, S. aureus, B. subtilis, and E. coli, and fungi, namely, A. flavus, A. parasiticus, and A. sp. The antibacterial and antifungal activities have been determined by measuring MIC values (μg/mL) and zone of inhibitions (mm). Among the tested compounds, it was found that compounds 3b, 9a, and 9b have most potent activity against S. aureus, A. flavus, and A. parasiticus, respectively, and were found to be more active than sulfamethoxazole and itraconazole with MIC values 40 μg/mL. In contrast, all the compounds were totally inactive against the A. sp. except 10b and 15b to show activity to some extent.
1. Introduction
Sulfonamides are basis of several drug groups, known as sulfa drugs. Any compound that has sulfonamide moiety (SO2NH2) in its structure is referred to as sulfonamide. They comprise substantial class of pharmaceutical drugs, containing various kinds of pharmacological agents having antitumor [1], antibacterial [2], anticarbonic anhydrase [3, 4], diuretic [5, 6], hypoglycemic [7], and protease inhibitory activity [8–10] or antithyroid activity [11] among others. Sulfonamides are mostly used to treat the bacterial infectious cells because they do not significantly affect the antigenic properties of the infective organism or the development of specific antibodies [12]. Bacteria have liability to acquire resistance against sulfonamides by changing their cell wall permeability, enhancing essential metabolites production, or increasing production of enzyme [13]. In this way sulfonamides become ineffective to inhibit their production. But their ineffectiveness in drug therapy can be abstained, due to inductive effect of SO2 group. Sulfonamides having first value around 10 are less soluble in water; therefore, they may readily crystalize in kidney but with advancement in medical science, and new sulfonamides have been synthesized having lower value (5-6) to avoid crystallization in kidney [14]. The compounds having pyridine and amide functional group exhibit various biological activities like antifungal and antibacterial. So these biological activities encourage us to synthesize the sulfonamides containing such important functional groups [15–18]. The motivation behind this research work was to synthesize some novel sulfonamides (Schemes 1–4) having antimicrobial properties. Different amines were chosen and reacted with sulfonyl chlorides. As a result of substitution, different functional groups were added and resulting compounds exhibited antibacterial and antifungal activities.
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