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US 2023/0266302 A1Published application
Synthesis and use of n-benzyl sulfonamides
AssigneeThe University of Tulsa
InventorsAngus A Lamar, Robert J Sheaff
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Abstract
Disclosed is a method for preparing N-benzyl sulfonamides. Also disclosed is a composition for treating cancer. The composition includes a N-benzyl sulfonamide and a metabolic inhibitor. Also disclosed is a method for determining the impact on cell ATP levels of a composition containing a N-benzyl sulfonamide with or without a metabolic inhibitor.
Claims25
A method for determining the cytotoxicity of a compound of interest, the method comprising:
- providing a first sample of living cells in a first test well;
- providing a second sample of living cells in a second test well;
- treating the first sample of living cells with the compound of interest;
- treating the second sample of living cells with a suitable control compound;
- selecting a luminescing detection agent and determining the time period for exposure of the first sample of living cells to the compound of interest which must pass prior to addition of the selected luminescing detection agent to said first sample of living cells and said second sample of living cells based on the selected luminescing detection agent;
- adding the luminescing detection agent to said first sample of living cells over a period of time as determined by the selected luminescing detection agent and adding said luminescing detection agent to said second sample of living cells over a period of time as determined by the selected luminescing detection agent;
- measuring the resulting luminescence produced by the first sample of living cells;
- measuring the resulting luminescence produced by the second sample of living cells;
- the difference between the luminescence of the first sample of living cells and the luminescence of the second sample of living cells reflects a reduction in ATP levels in the first sample of living cells which is indicative of the cytotoxicity of the compound of interest;
- and, said step of treating the first sample of living cells with the compound of interest does not result in cell death.
7 more elements
A composition comprising:
- a N-benzyl sulfonamide having the structure of Formula I:
- where R1 is an aromatic, heteroaromatic, or aliphatic alkyl group;
- and,
- where R3 is a heteroaromatic component.
1 more element
A method of preparing an N-benzyl sulfonamide comprising:
- providing a heteroaromatic compound having an aldehyde or carboxaldehyde functionality;
- providing a N-sulfonamide substrate;
- reacting the heteroaromatic compound with the N-sulfonamide substrate in the presence of elemental iodine and an oxidizing agent to form a N-sulfonyl imine, under non-acidic conditions, on the heteroaromatic scaffold of the heteroaromatic compound;
- converting the N-sulfonyl imine to a N-benzyl sulfonamide by addition of a reducing agent.
1 more element
A method of preparing an N-benzyl sulfonamide comprising:
- providing a heteroaromatic compound having an aldehyde or ketone functionality;
- providing a N-sulfonamide substrate in the form of an iminoiodinane reagent;
- reacting the heteroaromatic compound an iminoiodinane reagent;
- adding a reducing agent to the reaction mixture to provide the desired N-benzyl sulfonamide.
1 more element
Dependencies are inferred from the claim text.