Secnidazole-sulfonates: Synthesis, physical, electrochemical, antibacterial &amp; antifungal characteristics

Wahid, Sana; Hanif, Muddasir; Jahangir, Sajid; Shafique, Maryam; Shahid, Hafiz Abdullah; Muhammad, Haji; Shah, Syed Adnan Alı; Versiani, Muhammad Ali; Khan, Khalid Mohammed; Tahiri, Iftikhar Ahmad

doi:10.1016/j.molstruc.2019.02.068

Cited by 9 publications

(4 citation statements)

References 25 publications

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“…Sulfonate derivatives, owing to physicochemical properties, have a strong affinity for lipid phases and can cross the cuticle membrane easily to bind to target sites [23], and compounds containing aryl sulfonate moieties have received considerable attention due to extensive biological activities, and it has been proven to possess antiviral [24,25], antibacterial [26][27][28], insecticidal [29,30], anticancer [31,32], and other biological activity [33]. They were widely used in agricultural industries, medicine researches and other fields.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Zhou

Tang

et al. 2021

Monatsh Chem

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A series of myricetin derivatives containing sulfonate groups were designed and synthesized. Preliminary antibacterial activity showed that most of the target compounds exhibited significant biological activities against Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the EC50 value of compound 3e was 13.76 μg/cm3 against Xac, which was better than commercial reagents bismerthiazol (50.32 µg/cm3) and thiodiazole copper. (83.27 µg/cm3), and the EC50 value of compound 3j was 11.92 μg/cm3 against Xoo in vitro, The result was better than that of bismerthiazol (72.08 µg/cm3) and thiodiazole copper (99.26 µg/cm3). Compound 3j displayed the better in vivo activity against rice bacterial leaf blight than bismerthiazol and thiodiazole copper. Meanwhile, the antibacterial mechanism of compounds 3e and 3j was studied by scanning electron microscope (SEM). These results suggested that myricetin derivatives containing sulfonate can be considered as a new antibacterial reagents. Graphic abstract

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Zhou

Tang

et al. 2021

Monatsh Chem

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“…1d They have also been explored as synthetic auxiliaries, intermediates, protecting groups, and activating groups. 1c Furthermore, sulfonate ester derivatives have been utilized as the bifunctional DNA alkylating agents (such as busulfan and treosulfan), 3 monoamine oxidase A inhibitors, 4 P2X 7 receptor antagonist, 5 phospho-STAT3 inhibitor, 6 and antimicrotubule agents with antibacterial and antifungal properties (e.g., secnidazole sulfonate) 7 as shown in Figure 1, in clinical settings. As a result, the creation of these bioactive molecules containing sulfonate esters is in great demand.…”

Section: ■ Introductionmentioning

confidence: 99%

Convenient Synthesis of Salicylanilide Sulfonates from 1,2,3-Benzotriazin-4(3H)-ones and Organosulfonic Acids via Denitrogenative Cross-Coupling

et al. 2023

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An efficient and straightforward approach to synthesize salicylanilide aryl and alkyl sulfonates from 1,2,3-benzotriazin-4(3H)-ones and organosulfonic acids is described. This protocol is operationally simple and scalable, exhibits a broad substrate scope with high functional group tolerance, and affords the desired products in good to high yield. Application of the reaction is also demonstrated by converting the desired product to synthetically useful salicylamides in high yields.

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“…Several metronidazoles and secnidazole derivatives have been reported as potential α‐amylase, β‐glucuronidase inhibitors, and antimicrobial agents (Figure 1). [ 20–26 ] It is pertinent to mention that previous secnidazole derivatives were rarely investigated for the inhibition of AChE, BChE, α‐glucosidase, and carbonic anhydrase I and II enzymes. Thus, we are keen to explore the designed and synthesized secnidazole esters for the above‐mentioned indispensable drug targets.…”

Section: Introductionmentioning

confidence: 99%

“…Several metronidazoles and secnidazole derivatives have been reported as potential α-amylase, β-glucuronidase inhibitors, and antimicrobial agents (Figure 1). [20][21][22][23][24][25][26] It is pertinent to mention that previous secnidazole derivatives were rarely investigated for the inhibition of AChE, BChE, α-glucosidase, and carbonic anhydrase I and II F I G U R E 1 Already identified lead molecules based on metronidazole and secnidazole drugs and newly identified secnidazole derivatives 1-30 as acetylcholinesterase (AChE), butyrylcholinesterase (BChE), carbonic anhydrase I, II, and α-glucosidase inhibitors enzymes. Thus, we are keen to explore the designed and synthesized secnidazole esters for the above-mentioned indispensable drug targets.…”

Section: Introductionmentioning

confidence: 99%

Biology‐oriented drug synthesis and evaluation of secnidazole esters as novel enzyme ınhibitors

Ansari

Saad

Khan

et al. 2021

Archiv der Pharmazie

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The identification of novel compounds that can inhibit physiologically and metabolically important drug targets or enzymes has prime importance in medicinal chemistry. With this aim, a range of secnidazole esters 1–30 were synthesized under the heading of biology‐oriented drug synthesis by the 1,1′‐carbonyldiimidazole‐mediated coupling reaction between secnidazole and varyingly benzoic acid derivatives. All compounds were screened for inhibitory activity against human carbonic anhydrase (hCA) I and II, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α‐glucosidase. The results indicate that all the synthesized compounds showed potent inhibitory activities against all targets, as compared to the standard inhibitors, revealed by IC50 values. Ki values of the secnidazole derivatives 1–30 for hCA I, hCA II, AChE, BChE, and α‐glucosidase enzymes were obtained in the ranges of 47.37–190.74, 44.38–198.21, 12.14–68.37, 8.04–61.53, and 7.78–45.91 nM, respectively. To assess the enzyme–ligand interactions, the optimized most active compounds 2, 3, 8, 9, 14, 17, and 23 were subjected to molecular docking studies with modeled AChE, BChE, hCA I, hCA II, and α‐glucosidase enzymes, where several important and key interactions were monitored with amino acid residues of each target enzyme.

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Secnidazole-sulfonates: Synthesis, physical, electrochemical, antibacterial & antifungal characteristics

Cited by 9 publications

References 25 publications

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Convenient Synthesis of Salicylanilide Sulfonates from 1,2,3-Benzotriazin-4(3H)-ones and Organosulfonic Acids via Denitrogenative Cross-Coupling

Biology‐oriented drug synthesis and evaluation of secnidazole esters as novel enzyme ınhibitors

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