10311-89-4Relevant academic research and scientific papers
Design, synthesis, molecular modeling and anti-hyperglycemic evaluation of phthalimide-sulfonylurea hybrids as PPARγ and SUR agonists
El-Zahabi, Mohamed Ayman,Elbendary, Eman R.,Bamanie, Faida H.,Radwan, Mohamed F.,Ghareib, Salah A.,Eissa, Ibrahim H.
, (2019/07/16)
New series of phthalimide-sulfonylurea hybrids were prepared and examined for their in vivo anti-hyperglycemic activities in STZ-induced hyperglycemic rats using glibenclamide as a reference drug. Compounds 6c, 6d, 6g, 6h, 6j and 6k induced significant reduction in the blood glucose levels of diabetic rats ranging from 24.43 to 21.43%. Moreover, molecular docking and pharmacophore approaches were carried out to examine binding modes and fit values of the prepared compounds against PPARγ and SUR, respectively. Compounds 6c, 6d, 6j and 6m exhibited the highest binding free energies against PPARγ. Compounds 6c, 6j, 6k, 6l, and 6n showed the highest fit values against the generated pharmacophore model. Also, QSAR technique was carried out to estimate the proposed PPARγ binding affinities and insulin-secreting abilities. The synthesized compounds showed promising estimated activities. In-silico ADMET studies were performed to investigate pharmacokinetics of the synthesized compounds. They showed considerable human intestinal absorption with low BBB penetration.
Design and Synthesis of New 1,3,5-Trisubstituted Triazines for the Treatment of Cancer and Inflammation
Abbott, Shaun D.,Duceppe, Jean-Simon,Gagnon, Lyne,Geerts, Lilianne,Gervais, Liette,Grouix, Brigitte,Laurin, Pierre,Penney, Christopher L.,Perron, Valérie,Sarra-Bournet, Fran?ois,Wilb, Nicole,Zacharie, Boulos
, p. 737 - 749 (2018/10/05)
Low-molecular-weight synthetic molecules 1 with the general 2-(fluorophenylamino)-4,6-disubstituted 1,3,5-triazine structure and showing anti-inflammatory and anticancer activities were explored. Structure–activity relationship studies demonstrated the importance of the aminopentyl chain, the 3- or 4-fluorophenylaniline component, and the presence of at least one substituent, such as a tyramine moiety, attached directly to the triazine ring as essential for good activity. These compounds, represented by leads 4-{2-[4-(5-Aminopentylamino)-6-(3-fluorophenylamino)-1,3,5-triazin-2-ylamino]ethyl}phenol (6) and 4-{2-[4-(5-Aminopentylamino)-6-(4-fluorophenylamino)-1,3,5-triazin-2-ylamino]ethyl}phenol (10), displayed moderate and significant in vitro and in vivo dual activities, respectively, and address the molecular link between inflammation and cancer. Compound 10 demonstrated significant antitumor efficacy upon administration by the oral and intravenous routes in several animal models. This class of triazine compounds is new, safe, and nontoxic and offers a novel approach to the treatment of inflammation and cancer.
Synthesis and biological evaluation of cyclic imides incorporating benzenesulfonamide moieties as carbonic anhydrase I, II, IV and IX inhibitors
Abdel-Aziz, Alaa A.-M.,Angeli, Andrea,El-Azab, Adel S.,Abu El-Enin, Mohamed A.,Supuran, Claudiu T.
, p. 1666 - 1671 (2017/02/26)
A group of cyclic imides was synthesized by reaction of amino-substituted benzenesulfonamides with a series of acid anhydrides such as succinic, maleic, tetrahydrophthalic, pyrazine-2,3-dicarboxylic acid anhydride, and substituted phthalic anhydrides. The synthesized sulfonamides were evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors against the human (h) isoforms hCA I, II, IV and IX, involved in a variety of diseases among which glaucoma, retinitis pigmentosa, etc. Some of these sulfonamides showed effective inhibitory action (in the nanomolar range) against the cytosolic isoform hCA II and the transmembrane, tumor-associated one hCA IX, making them interesting candidates for preclinical evaluation in glaucoma or various tumors in which the two enzymes are involved. hCA I and IV were on the other hand less inhibited by these sulfonamides, with inhibition constants in the micromolar range.
"TRIAZINE DERIVATIVES, COMPOSITIONS CONTAINING SUCH DERIVATIVES, AND METHODS OF TREATMENT OF CANCER AND AUTOIMMUNE DISEASES USING SUCH DERIVATIVES"
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Page/Page column 17-18, (2008/12/08)
We describe compounds of the following general formula (I): wherein X is fluorine or chlorine; Y is oxygen, sulfur, or an amino group; R is an amino, hydroxyl, sulfonamide, or carboxamide group or an N-monomethyl or N-dimethyl analog thereof; m is an integer from 2 to 6, and n is an integer from 0 to 2. The compounds may be used for treating certain cancers and autoimmune diseases.
