Bio-Potent Sulfonamides

Dineshkumar, S.; Thirunarayanan, Ganesamoorthy

doi:10.4067/s0717-97072019000104386

Cited by 4 publications

(3 citation statements)

References 28 publications

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“…The displacement of the bands can be attributed to changes in the vibrational frequency characteristic of the ν(C-C) bond in the pyridine molecule due to its involvement in the coordination of the Cu +2 ion through the nyridinic atom. The features of the IR spectrum of the complex are similar to those reported for the other copper N -sulfonamide derivatives [ 33 , 34 , 35 ] and demonstrate the existence of new linkages within the complex ( Figures S1 and S2 Supplementary Materials ).…”

Section: Resultssupporting

confidence: 71%

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

et al. 2022

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Nowadays, the discovery of a new non-toxic metal complex with biological activity represents a very active area of research. Two Cu+2 complexes, [Cu(L1)2(H2O)3] (C1) (HL1= N-(5-(4-methylphenyl)-[1,3,4]–thiadiazole–2-yl)-naphtalenesulfonamide) and [Cu(L2)2(py)2(H2O)] (C2) (HL2= N-(5-ethyl-[1,3,4]–thiadiazole–2-yl)-naphtalenesulfonamide), with two new ligands were synthesized. The X-ray crystal structures of the complexes were determined. In both complexes, Cu+2 is five-coordinated, forming a CuN2O3 and CuN4O chromophore, respectively. The ligands act as monodentate, coordinating the metal ion through a single Nthiadiazole atom; for the C2 complex, the molecules from the reaction medium (pyridine and water) are also involved in the coordination of Cu+2. The complexes have a distorted square pyramidal square-planar geometry. The compounds were characterized by FT-IR, electronic EPR spectroscopy, and magnetic methods. The nuclease activity studies confirm the complexes’ capacity to cleave the DNA molecule. Using a xanthine-xanthine oxydase system, the SOD mimetic activity of the complexes was demonstrated. Cytotoxicity studies were carried out on two tumor cell lines (HeLa, WM35) and on a normal cell line (HFL1) using the MTT method, with cisplatin used as a positive control. The antibacterial activity of the complexes was investigated against two Gram-positive and two Gram-negative bacteria, and compared with Amoxicillin and Norfloxacin using the disk diffusion method. Both complexes showed in vitro biological activity but the C2 complex was more active. A lack of in vivo toxicity was demonstrated for the C2 complex by performing hepatic, renal, and hematological studies on Swiss mice.

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Section: Resultssupporting

confidence: 71%

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

et al. 2022

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“…Nevertheless, only the sulfonyl fluorides were observed for aliphatic NÀ CF 3 secondary amines (25)(26)(27)(28)(29)(30)(31). Finally, to demonstrate the potential of this new construction method for NÀ CF 3 sulfonamides to prepare drug-like molecules, we have undertaken the synthesis of bioactive molecules (76), [39] benzocaine derivatives (77), and the attractive sulfamethoxazole derivatives (78). [36] Sulfamethoxazole is a commonly used anti-infective drug, and its NÀ CF 3 derivative was obtained by reducing compound 71 [36] (combination of isoxazole secondary amine 20 with pnitrobenzenesulfonyl bromide) with palladium-carbon (Figure 3).…”

Section: Methodsmentioning

confidence: 99%

General Access to N−CF₃ Secondary Amines and Their Transformation to N−CF₃ Sulfonamides

Wang

et al. 2022

Angew Chem Int Ed

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The synthesis of NÀ CF 3 compounds through fluorination or trifluoromethylation of N-containing compounds has been extensively investigated. However, general access to NÀ CF 3 compounds simply from NÀ CF 3 secondary amines is hampered by the challenging preparation and instability of these amines, as well as a much lower reactivity due to the strong electron-withdrawing nature and steric bulk of the trifluoromethyl moiety. Herein, we report a general and highly efficient synthesis of NÀ CF 3 secondary amines with excellent isolated yields via the addition of the in situ generated difluoromethyl imine (RÀ N=CF 2 ) intermediates with hydrogen fluoride, which is mildly produced by triethylsilane and silver fluoride. NÀ CF 3 sulfonamides, highly desirable but scarce at present, are easily accessible from these valuable building blocks through an unprecedented route. This study will bring new vitality to the synthesis of NÀ CF 3 compounds.

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“…Nevertheless, only the sulfonyl fluorides were observed for aliphatic NÀ CF 3 secondary amines (25)(26)(27)(28)(29)(30)(31). Finally, to demonstrate the potential this new construction method for NÀ CF 3 sulfonamides to prepare drug-like molecules, we have undertaken the synthesis of bioactive molecules (76), [39] benzocaine derivatives (77), and the attractive sulfamethoxazole derivatives (78). [36] Sulfamethoxazole is a commonly used anti-infective drug, and its NÀ CF 3 derivative was obtained by reducing compound 71 [36] (combination of isoxazole secondary amine 20 with pnitrobenzenesulfonyl bromide) with palladium-carbon (Figure 3).…”

Section: Zuschriftenmentioning

confidence: 99%

General Access to N−CF₃ Secondary Amines and Their Transformation to N−CF₃ Sulfonamides

Wang

et al. 2022

Angewandte Chemie

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The synthesis of N−CF3 compounds through fluorination or trifluoromethylation of N‐containing compounds has been extensively investigated. However, general access to N−CF3 compounds simply from N−CF3 secondary amines is hampered by the challenging preparation and instability of these amines, as well as a much lower reactivity due to the strong electron‐withdrawing nature and steric bulk of the trifluoromethyl moiety. Herein, we report a general and highly efficient synthesis of N−CF3 secondary amines with excellent isolated yields via the addition of the in situ generated difluoromethyl imine (R−N=CF2) intermediates with hydrogen fluoride, which is mildly produced by triethylsilane and silver fluoride. N−CF3 sulfonamides, highly desirable but scarce at present, are easily accessible from these valuable building blocks through an unprecedented route. This study will bring new vitality to the synthesis of N−CF3 compounds.

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Bio-Potent Sulfonamides

Cited by 4 publications

References 28 publications

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

General Access to N−CF₃ Secondary Amines and Their Transformation to N−CF₃ Sulfonamides

General Access to N−CF₃ Secondary Amines and Their Transformation to N−CF₃ Sulfonamides

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Bio-Potent Sulfonamides

Cited by 4 publications

References 28 publications

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

New Cu+2 Complexes with N-Sulfonamide Ligands: Potential Antitumor, Antibacterial, and Antioxidant Agents

General Access to N−CF3 Secondary Amines and Their Transformation to N−CF3 Sulfonamides

General Access to N−CF3 Secondary Amines and Their Transformation to N−CF3 Sulfonamides

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General Access to N−CF₃ Secondary Amines and Their Transformation to N−CF₃ Sulfonamides

General Access to N−CF₃ Secondary Amines and Their Transformation to N−CF₃ Sulfonamides