Design and biological evaluation of a novel type of potential multi-targeting antimicrobial sulfanilamide hybrids in combination of pyrimidine and azoles

Sui, Yan-Fei; Li, Di; Wang, Juan; Bheemanaboina, Rammohan R. Yadav; Ansari, Mohammad Fawad; Gan, Lin-Ling; Zhou, Cheng‐He

doi:10.1016/j.bmcl.2020.126982

Cited by 51 publications

(33 citation statements)

References 49 publications

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“…1 H NMR (600 MHz, DMSO-d 6 ) δ 13.14 (s, 1H, imidazole-NH), 11.51 (s, 1H, barbituric acid-NH), 11.41 (s, 1H, barbituric acid-NH), 7.97 (s, 1H, CH), 2.86 (t, J = 7. 5…”

Section: (E)-5-((2-butyl-4-chloro-1h-imidazol-5-yl)methylene) Pyrimidine-246 (1h3h5h)-trione (2)mentioning

confidence: 99%

“…1 H NMR (600 MHz, CDCl 3 ) δ 13.28 (s, 1H, imidazole-NH), 8.41 (s, 1H, CH), 3.94 (t, J = 7.3 Hz, 2H, NCH 2 ), 2.85 (t, J = 7. 5 13, 138.31, 123.45, 106.97, 41.89, 31.88, 30.83, 29.74-29.39, 29.39-29.03, 27.97, 26.84, 22.64, 22.26, 14.10…”

Section: (E)-5-((2-butyl-4-chloro-1h-imidazol-5-yl)methylene)-1-octylpyrimidine-246(1h3h5h)-trione (3 D)mentioning

confidence: 99%

“…Compound 5 i was obtained as yellow solid (434 mg), melting point: > 250°C, yield: 59.6%. 1 H NMR (600 MHz, DMSO-d 6 ) δ 13.15 (s,1H,11.89 (s,1H,8.18 (d,J = 2.3 Hz,1H,CH),8.04 (s,1H,5,5.11 (s,2H,NCH 150.76, 147.16, 146.60, 146.31, 145.26, 135.22, 128.90, 128.54, 123.90, 122.59, 109.51, 44.06, 29.61, 29.46, 28.35, 22.10, 14. Biological assays procedures Minimal inhibitory concentration (MIC, mM) is defined as the lowest concentration of target compounds that completely inhibit the growth of bacteria, by means of standard twofold serial dilution method in 96-well microtest plates according to the Clinical and Laboratory Standards Institute (CLSI). The tested microorganism strains were provided by the School of Pharmaceutical Sciences, Southwest University and the College of Pharmacy, Third Military Medical University.…”

Section: (E)-5-((2-butyl-4-chloro-1h-imidazol-5-yl)methylene)-1-octadecyl Pyrimidine-246(1h3h5h)-trione (3 F)mentioning

confidence: 99%

“…[3] Pyrimidine as a fascinating aromatic heterocycle with planar six-membered unsaturated ring plays a positive role in genetic information transmission and expression, [4] whose derivatives have attracted more and more attention due to vast range of applications. [5] The clinical drugs such as 5-flucytosine, voriconazole, abafungin and hexetidine are prevalent in antifungal therapies. [6] Pyrimidinetrione analogs have been extensively explored as medicinal agents including psychotropic, anticancer, antimicrobial, and anti-seizure agents.…”

Section: Introductionmentioning

confidence: 99%

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Pyrimidinetrione‐imidazoles as a Unique Structural Type of Potential Agents towards Candida Albicans: Design, Synthesis and Biological Evaluation

Sui

Ansari

Zhou

2021

Chemistry An Asian Journal

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Substantial morbidity and mortality of fungal infections have aroused concerns all over the world, and common Candida spp. currently bring about severe systemic infections. A series of pyrimidinetrione-imidazole conjugates as potentially antifungal agents were developed. Bioassays manifested that 4fluobenzyl pyrimidinetrione imidazole 5 f exerted favorable inhibition towards C. albicans (MIC = 0.002 mM), being 6.5 folds more active than clinical antifungal drug fluconazole (MIC = 0.013 mM). Preliminary mechanism research indicated that compound 5 f could not only depolarize membrane potential but also permeabilize the membrane of C. albicans. Molecular docking was operated to simulate the interaction mode between molecule 5 f and CYP51. In addition, hybrid 5 f might form 5 f-DNA supramolecular complex via intercalating into DNA. The interference of membrane and DNA might contribute to its fungicidal capacity with no obvious tendency to induce the resistance against C. albicans. Conjugate 5 f endowed good blood compatibility as well as low cytotoxicity towards HeLa and HEK-293T cells.

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“…1 H NMR (600 MHz, DMSO-d 6 ) δ 13.14 (s, 1H, imidazole-NH), 11.51 (s, 1H, barbituric acid-NH), 11.41 (s, 1H, barbituric acid-NH), 7.97 (s, 1H, CH), 2.86 (t, J = 7. 5…”

Section: (E)-5-((2-butyl-4-chloro-1h-imidazol-5-yl)methylene) Pyrimidine-246 (1h3h5h)-trione (2)mentioning

confidence: 99%

Section: (E)-5-((2-butyl-4-chloro-1h-imidazol-5-yl)methylene)-1-octylpyrimidine-246(1h3h5h)-trione (3 D)mentioning

confidence: 99%

Section: (E)-5-((2-butyl-4-chloro-1h-imidazol-5-yl)methylene)-1-octadecyl Pyrimidine-246(1h3h5h)-trione (3 F)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Pyrimidinetrione‐imidazoles as a Unique Structural Type of Potential Agents towards Candida Albicans: Design, Synthesis and Biological Evaluation

Sui

Ansari

Zhou

2021

Chemistry An Asian Journal

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“…[53,54] antifungal, [55,56] antiviral, [57][58][59] antibacterial, [60] antimalarial, [61] anti-HIV, [62,63] antiulcer, [64] insecticide, [65] antineoplastic, [66] antiepileptic, [67] analgesic, [68] and anthelmintic. [69] Several commercially available drugs derived from pyrimidine are sildenafil (viagra), formycin A, [70] sulfadiazine, [71] pyrimethamine, [72] roscovitine, [73] indiplon, zaleplon, [74] ocinaplon, [75] dinaciclib, [75] fluorastrol, [76] 5-fluorouracil, [77] ispinesib, [78] volasertib, [79] pictilisib, monastrol, [80] and etravirine [81] (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Farooq

Ngaini

2021

Journal of Heterocyclic Chem

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Chalcone-derived pyrimidine is a well-known heterocyclic compound that is commonly present in ribonucleic acid (RNA) and deoxyribonucleic acid (DNA) bio-isosteres. Pyrimidine derivatives are effective in both the electronic industry and drug industries. This review highlights the synthesis of pyrimidines, namely mono-pyrimidine, bis-pyrimidine, fused pyrimidine, symmetric, and asymmetric pyrimidine via one-pot and two-pot methods. The one-pot method is the direct reaction of amino derivatives with aldehydes and acetophenones, whereas the two-pot method is frequently reported for the synthesis of chalcone before the cyclization to a pyrimidine. This review is important in organic synthesis, particularly in the heterocyclic field, regarding pyrimidines and their significance in therapeutic and electronic industries.

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Novel Schiff Base‐conjugated para‐Aminobenzenesulfonamide Indole Hybrids as Potentially Muti‐targeting Blockers against Staphylococcus aureus

Zhang

Huang

et al. 2022

Asian J Org Chem

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Staphylococcus aureus (S. aureus) has developed strong resistance to a variety of clinical antibiotics, which makes the design and synthesis of novel structural molecules with outstanding antibacterial potential put on the agenda. The results of bioactivity assessment displayed that sulfonamide indole compound 4 h, which was modified with a butene group, had remarkable antibacterial activity against S. aureus (MIC=5 μM), and was superior to the reference drugs norfloxacin (MIC=13 μM) and sulfathiazole (MIC=501 μM). The propensity of evaluation of hybrid 4 h to induce drug resistance was lower than that of the reference drugs. In addition, the cytotoxicity assay revealed that compound 4 h had no obvious cytotoxicity to normal mammalian cells (RAW 264.7). Molecular docking analysis further demonstrated that the highly active molecule 4 h could interact with the active sites of DNA hexamer duplex and human carbonic anhydrase isozyme II through hydrogen bonds. Moreover, preliminary mechanistic studies indicated that hybrid 4 h prospectively acted as an blocker by disrupting the bacterial membrane of S. aureus and inserting itself into S. aureus DNA to prevent strains from replicating.

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Design and biological evaluation of a novel type of potential multi-targeting antimicrobial sulfanilamide hybrids in combination of pyrimidine and azoles

Cited by 51 publications

References 49 publications

Pyrimidinetrione‐imidazoles as a Unique Structural Type of Potential Agents towards Candida Albicans: Design, Synthesis and Biological Evaluation

Pyrimidinetrione‐imidazoles as a Unique Structural Type of Potential Agents towards Candida Albicans: Design, Synthesis and Biological Evaluation

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Novel Schiff Base‐conjugated para‐Aminobenzenesulfonamide Indole Hybrids as Potentially Muti‐targeting Blockers against Staphylococcus aureus

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