3306-62-5Relevant articles and documents
Easy preparation of novel 3,3-dimethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide: Molecular structure, Hirshfeld surface, NCI analyses and molecular docking on AMPA receptors
Etsè, Koffi Sénam,Zaragoza, Guillermo,Etsè, Kodjo Djidjolé
, (2021/04/27)
We present in this study the synthesis and characterization of a new 3,3-dimethyl-substituted 1,2,4-benzothiadiazine 1,1-dioxide. 3,3-dimethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide 10, was obtained by reacting 2-aminobenzenesulfonamide with acetone. The molecular structures of the starting sulfonamide and the new benzothiadiazine were obtained by X-ray diffraction analysis and the interactions like hydrogen bonds stabilizing the crystal packing were discussed. The contacts are confirmed by non-covalent interaction analysis. Analyses of Hirshfeld surface mapped over di, de, dnorm and shape-index were further used to identify the intermolecular interactions. The fingerprint histogram allow to show that H···H (45.7%) and O···H (30.1%) contacts are the dominant interactions in the crystal packing of 10. The effects of the molecular environment were accessed by analyzing the electron density isosurface and the 3D-topology of energy frameworks. The prediction of physicochemical properties suggested that 10 could be considered as a lead-like drug. Therefore, molecular docking study was performed on the α-amino-3?hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR) and suggested that 10 could interact with the allosteric site located on the ligand binding domain of AMPAR and could be a positive allosteric modulator. Docking results show that 10 can bind in a symmetrical way in the GluA2 ligand binding domain with two molecules at the dimer interface. The results also demonstrated that the presence of two methyl groups at the 3-position of the thiadiazine ring induced rotation of 10 in the binding site leading to close contacts with Pro494, Ser497, Ser729 and Ser754.
Benzothiadiazine methoxy acrylate derivatives and preparation method and application thereof
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Paragraph 0023-0025, (2020/07/24)
The invention provides benzothiadiazine methoxy acrylate derivatives and a preparation method and application thereof, and the benzothiadiazine methoxy acrylate derivatives have the following chemicalstructural general formula VII as shown in the description, wherein R1 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy or nitro; and R2 is hydrogen, methyl or benzyl. According to the invention, an active group 3, 4-dihydro-2H-1, 2, 4-benzothiadiazine-1, 1-dioxo substitutes the side chain part of the methoxy acrylate bactericide and then is reasonably spliced with the pharmacophore of the methoxy acrylate bactericide, so that the bactericide with novel structure, broad spectrum, high efficiency and low toxicity is synthesized, the bactericide can be alternately used with the existing bactericide, the generation of resistance is avoided or delayed, the preparation conditions are conventional, the subsequent treatment is simple and convenient, and the industrialization is easy to realize.
Iridium-Catalyzed ortho-C?H Amidation of Benzenesulfonamides with Sulfonyl Azides
Hou, Hongcen,Zhao, Yongli,Sheng, Shouri,Chen, Junmin
, p. 4393 - 4398 (2019/08/28)
We developed herein an iridium-catalyzed direct C?H activation/ C?N bond formation reaction of benzenesulfonamides with sulfonyl azides. The amidation reaction provides a protocol for the synthesis of 2-aminobenzesulfonamides in good to excellent yields. This strategy features a wide substrate scope, tolerates a broad range of functional groups under external oxidant-free conditions and only releases molecular nitrogen as the sole by-product. Moreover, the preliminary mechanism was investigated and the proposed reaction pathway was provided. (Figure presented.).
