Synthesis and biological evaluation of pyrimidinyl sulphonamide derivatives as promising class of antitubercular agents

Abstract

A small library of compounds are synthesized and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37RV. Two compounds, -[(2 0 ,4 0 -dinitrophenyl) sulphonyl]-4-(p-aminophenylsulphonylamino)-6-(2 0 -chlorophenyl)-pyrimidine-5-carboxamide F b and 2-hydrazino-4-(p-aminophenylsulphonylamino)-6-(2 0 -chlorophenyl)-pyrimidine-5-carboxamide D b were found to be the most active compounds in vitro with MIC of 0.02 lg/mL against MTB and were more potent compared to isoniazid (MIC: 0.03 lg/mL). ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Chromene-Containing Aromatic Sulfonamides with Carbonic Anhydrase Inhibitory Properties

“…The classical CA inhibitors (CAIs) are the primary sulfonamides, which coordinate the zinc ion with their terminal deprotonated nitrogen atom and have been in clinical use for more than 70 years as diuretics and systemically acting antiglaucoma drugs [ 10 ]. Chromenes have attracted the interest of the scientific community due to their wide range of biological activities, such as antimicrobial [ 11 , 12 ], anticancer [ 13 , 14 ], anti-inflammatory [ 15 , 16 ], and CA inhibitors [ 17 , 18 , 19 , 20 , 21 ], nematicidal [ 22 ], antiallergic [ 23 ] Some sulfonamides also show antimicrobial [ 24 , 25 ], anticancer [ 26 , 27 ], antidiabetic [ 28 ], anti-inflammatory [ 15 , 29 ], and antitubercular [ 30 ] activities. Taking into account all of the above-mentioned, here we report the synthesis of (4-sulfamoylphenyl)-4 H -chromene-2-carboxamide derivatives for its incorporation into one scaffold chromene and sulfonamide moieties.…”

An overview of sulfonamide‐based conjugates: Recent advances for tuberculosis treatment

“…Among all promising chemical structures ( 68 – 85 , 87 – 101 , 103–107 ; MIC = 6.25 μg/ml −1 ), conjugates ( 86 , 102 ) exhibited the most potent MIC values (0.02 μg/ml −1 ) (Figure 9b). These two compounds ( 86 , 102 ) had their cytotoxicity profiles measured against VERO cell lines, showing IC 50 values of 13.96 μg/ml −1 and 79.55 μg/ml −1 (SI = 2.23 and 12.72), respectively (Bhuva et al, 2017).…”

“…(a) New pyrimidinyl‐based sulphonamide conjugates ( 68 – 87 ) (Bhuva et al, 2017). (b) New pyrimidinyl‐based sulphonamide conjugates ( 88 – 107 ) (Bhuva et al, 2017)…”

“…Against 57,[59][60][61][62][63]66) showed MIC ranges between 8.0-500.0 μM (Krátký et al, 2017). Bhuva and co-workers (2015) assessed a series of 40 novel pyrimidinyl-based sulphonamide analogues (68-107); the results showed satisfactory anti-Mtb (H 37 Rv) effects (Bhuva et al, 2017). Among all promising chemical structures (68-85, 87-101, 103-107; MIC = 6.25 μg/ml À1 ), conjugates (86, 102) exhibited the most potent MIC values (0.02 μg/ml À1 ) (Figure 9b).…”

New Sulfanilamide Derivatives Incorporating Heterocyclic Carboxamide Moieties as Carbonic Anhydrase Inhibitors

“…In addition, furano- and thienopyroles have attracted interest of medicinal chemists due to their wide range of biological activities, such as antiviral [ 19 , 20 , 21 ], antimicrobial [ 22 , 23 , 24 ], anticancer [ 25 , 26 , 27 ], anti-inflammatory [ 28 , 29 ], antidiabetic [ 30 ], carbonic anhydrase inhibitory [ 31 ]. On the other hand, some sulfonamides also show anticancer [ 32 , 33 ], antimicrobial [ 34 , 35 ], anti-inflammatory [ 36 , 37 ] antidiabetic [ 38 ], and antitubercular [ 39 ] activities.…”