In silico Investigation and Biological Evaluation of Synthesized Sulfamethoxazole Derivatives

Sahoo, Jagannath; Kshiroda, Priyambada; Sarangi, Nandini; Rout, Susanta Kumar; Paidesetty, Sudhir Kumar

doi:10.36468/pharmaceutical-sciences.629

Cited by 4 publications

(2 citation statements)

References 9 publications

(19 reference statements)

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“…In recent years, a great number of sulfamethoxazole derivatives were synthesized, characterized and tested to obtain high-potency agents for clinical purposes. The investigations have disclosed analgesic, antioxidant, antimicrobial [29], antibacterial [30][31][32][33], and antifungal [32,33] properties of newly synthesized derivatives. They proved to be promising starting points for the development of new antichlamydial medications [34] and HSP70 inhibitors [35].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

et al. 2023

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A series of new derivatives based on sulfamethoxazole were designed and synthesized in this study. The structures of the new compounds were confirmed based on a comprehensive characterization of spectral data by applied IR and 1H as well as 13C NMR spectroscopy. The prepared compounds were tested for their anticancer and antimicrobial properties. Hydrazone 16b demonstrated convincing anticancer effect against all tested cell cultures such as human prostate carcinoma PPC-1 and human kidney carcinoma CaKi-1 cell lines, and human fibroblasts HF, n = 3. The most promising compound 16b showed higher activity against CaKi-1 cell line than the anticancer drugs axitinib and pazopanib used to treat renal cancer. Also, it was more active in the PPC-1 cell line compared to the approved PARP inhibitor Olaparib. Hydrazone 16b was also found to possess good antimicrobial properties against gram-positive bacteria strains of Staphylococcus aureus, Staphylococcus epidermidis, as well as Bacillus cereus.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

et al. 2023

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“…Since the molecular structure of sulfonyl amides is similar to the structure of the p -aminobenzoic acid being synthesized in our body, it interferes with the reactions controlled by this agent and affects the functioning of the metabolism [ 22 , 23 ]. The more acidic character of the hydrogens on the nitrogen of the N -substituted sulfonyl amides in this class causes it to form stronger hydrogen bonds and thus increase its activity [ 24 – 29 ] (Scheme S2).…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic effect, enzyme inhibition, and in silico studies of some novel N-substituted sulfonyl amides incorporating 1,3,4-oxadiazol structural motif

et al. 2022

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The acetylcholinesterase and carbonic anhydrase inhibitors (AChEIs and h CAIs) remain key therapeutic agents for many bioactivities such as anti-Alzheimer and antiobesity antiepileptic, anticancer, antiinfective, antiglaucoma, and diuretic effects. Here, it has been attempted to discover novel multi-target AChEIs and h CAIs that are highly potent, orally bioavailable, may be brain penetrant, and have higher effectiveness at lower doses than tacrine and acetazolamide. After detailed investigations both in vitro and in silico, novel N -substituted sulfonyl amide derivatives ( 6a–j ) were determined to be highly potent inhibitors for AChE and h CAs ( K I s are in the range of 23.11–52.49 nM, 18.66–59.62 nM, and 9.33–120.80 nM for AChE, h CA I, and h CA II, respectively). Moreover, according to the cytotoxic effect studies, such as the ADME-Tox, cortex neuron cells, and neuroblastoma SH-SY5Y cell line, compounds 6a , 6d , and 6h , which are the most potent representative versus the target enzymes, were identified as orally bioavailable, highly selective, and brain preferentially distributed AChEIs and h CAIs. The docking studies revealed precise binding modes between 6a , 6d , and 6h and h CA II, h CA I, and AChE, respectively. The results presented here might provide a solid basis for further investigation into more potent AChEIs and h CAIs. Graphical abstract Supplementary Information The online version contains supplementary material available at 10.1007/s11030-022-10422-8.

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Synthesis and Antibacterial Activity of Azo-Sulfa-Based Disperse Dyes and Their Application in Polyester Printing

et al. 2023

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For conjugating sulfa drug moieties with Schiff’s bases scaffold in the same build through an azo linker to take advantage of the bioactive feature of both motifs, we designed and synthesized a series of bioactive disperse dyes. The target disperse dyes, methyl 2-(E-2-hydroxy-5-((E)-(4-sulfa-derivative) diazenyl)benzylidene) hydrazine-1-carbodithioates 4a–e have been synthesized via the acidic reaction of azo dyes 3a–e with methyl hydrazine carbodithioate. Structures of the synthesized dyes were clarified based on their spectral and elemental analyses. The effectiveness of the dyes was initially tested as an antibacterial toward Staphylococcus aureus ATCC 6538-P and Escherichia coli ATCC 25933. Dyes that were proven to be effective against bacteria have been used as disperse dyes to print polyester fabrics. The color properties of the dyes and their fastness properties counting washing, perspiration, light, rubbing, and sublimation fastness were also examined. The printed polyester fabrics were evaluated for their antibacterial activity via colony-forming unit (CFU) technique. Fabric samples treated with 4c, 4d, and 4b had promising anti-Gram-positive activities against S. aureus. Whereas 4c-, 4d-, and 4b-treated fabrics exhibited moderate anti-Gram-negative activities against the test bacterium E. coli.

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In silico Investigation and Biological Evaluation of Synthesized Sulfamethoxazole Derivatives

Cited by 4 publications

References 9 publications

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

Synthesis of novel sulphamethoxazole derivatives and exploration of their anticancer and antimicrobial properties

Cytotoxic effect, enzyme inhibition, and in silico studies of some novel N-substituted sulfonyl amides incorporating 1,3,4-oxadiazol structural motif

Synthesis and Antibacterial Activity of Azo-Sulfa-Based Disperse Dyes and Their Application in Polyester Printing

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