28824-66-0Relevant academic research and scientific papers
Design and microwave synthesis of new (5z) 5-arylidene-2-thioxo-1,3-thiazolinidin-4-one and (5z) 2-amino-5-arylidene-1,3-thiazol-4(5h)-one as new inhibitors of protein kinase dyrk1a
Bazureau, Jean-Pierre,Bourahla, Khadidja,Carreaux, Fran?ois,Charlier, Thierry,Durieu, Emilie,Guihéneuf, Solène,Le Guével, Rémy,Limanton, Emmanuelle,Lozach, Olivier,Meijer, Laurent,Paquin, Ludovic,Rahmouni, Mustapha
supporting information, (2021/11/08)
Here, we report on the synthesis of libraries of new 5-arylidene-2-thioxo-1,3-thiazolidin-4-ones 3 (twenty-two compounds) and new 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones 5 (twenty-four compounds) with stereo controlled Z-geometry under microwave irradi
Leucettamine B analogs and their carborane derivative as potential anti-cancer agents: Design, synthesis, and biological evaluation
Chang, Jui-Hsun,Cheng, Tsai-Mu,Chu, Hsueh-Liang,Horng, Jia-Cherng,Hsieh, Cheng-Ying,Hsu, Kai-Cheng,Hsu, Ming-Hua,Kapoor, Mohit,Lin, Tony Eight,Tsai, Fu-Yuan
, (2020/03/17)
Leucettamine B is a natural product found in marine sponge Leucetta microraphis. Several of analogs of its family, such as aplysinopsine and clathridine, are medicinally active molecules which have applications in many pharmaceuticals and healthcare products; however, thus far, leucettamine B has not been studied. In this report, we describe the synthesis of a new class of analogs of leucettamine B obtained by Knoevenagel condensation using a microwave reactor. The 25 newly synthesized compounds were tested against MDA-MB-468, SW480, and Mahlavu cell lines for anticancer activity. Among them, the carborane-based compound (Z)-5-(benzo[d][1,3]dioxol-5-ylmethylene)-3-(1-closo-carboranyl)-2-thioxo -thiazolidin-4-one (49) and (Z)-5-(benzo[d][1,3]dioxol-5-ylmethylene)-3-(2-(pyrrolidin-1-yl)ethyl)-2-thioxothiazolidin-4-one (31) derivatives were found to have the most potential for use against tumor cells. The carborane derivative 49 had the lowest IC50 value against the SW480 cell line (4.7 μM) and the Mahlavu (6.6 μM) cell line. Furthermore, compound 31 also had a low IC50 value against SW480 (7.5 μM). Our research shows that leucettamine B analogs might have potential for use in cancer chemotherapy.
Uses of 2-(thiophene-2-carbonylcarbamothioylthio)acetic acid as a good synthon for construction of some new thiazole and annulated thiazole derivatives
El-Mawgoud, Heba Kamal Abd,Atta-Allah, Saad Ramadan,Hemdan, Magdy Mohamed
, p. 992 - 998 (2018/10/08)
The reaction of thiophene-2-carbonyl isothiocyanate 2 with thioglycolic acid gave 2-(thiophene-2-carbonylcarbamothioylthio) acetic acid 3. Compound 3 was subjected to some selected reactions with sulphuric acid as well as benzaldehyde, piperonal and isati
Design and Synthesis of 5-Substituted Benzo[d][1,3]dioxole Derivatives as Potent Anticonvulsant Agents
Dong, Shiyang,Wang, Tiantian,Hu, Chundi,Chen, Xiaodong,Jin, Yi,Wang, Zengtao
, (2017/02/15)
A series of 5-substituted benzo[d][1,3]dioxole derivatives was designed, synthesized, and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Neurotoxicity was determined by rotarod test. In the preliminary screening, six compounds, 3a, 3c, 3d, and 4d–f, showed promising anticonvulsant activities in the MES model, and compounds 4c and 4d exhibited full protection against seizures at doses of 300 mg/kg in the scPTZ model. Among the synthesized compounds, 3c as the most active compound showed high protection against the MES-induced seizures with an ED50 value of 9.8 mg/kg and a TD50 value of 229.4 mg/kg after intraperitoneal injection into mice, thus providing compound 3c with a high protective index (TD50/ED50) of 23.4 comparable to those of reference antiepileptic drugs.
Microwave-Assisted condensation reactions of acetophenone derivatives and activated methylene compounds with aldehydes catalyzed by boric acid under solvent-free conditions
Brun, Elodie,Safer, Abdelmounaim,Carreaux, Franois,Bourahla, Khadidja,L'Helgoua'ch, Jean-Martial,Bazureau, Jean-Pierre,Villalgordo, Jose Manuel
, p. 11617 - 11631 (2015/08/06)
We here disclosed a new protocol for the condensation of acetophenone derivatives and active methylene compounds with aldehydes in the presence of boric acid under microwave conditions. Implementation of the reaction is simple, healthy and environmentally
Design and synthesis of novel bis-thiazolone derivatives as micromolar CDC25 phosphatase inhibitors: Effect of dimerisation on phosphatase inhibition
Sarkis, Manal,Tran, Diem Ngan,Kolb, Stephanie,Miteva, Maria A.,Villoutreix, Bruno O.,Garbay, Christiane,Braud, Emmanuelle
, p. 7345 - 7350 (2013/02/23)
CDC25 phosphatases are involved in deregulated cell cycle progression and tumor development with poor prognosis. Among the most potent CDC25 inhibitors, quinonoid-based derivatives have been extensively studied. Dimerisation of heterocyclic quinones has led to IRC-083864, a bis-quinone compound with increased CDC25B inhibitory activity. Thirty-one bis-thiazolone derivatives were synthesized and assayed for CDC25 inhibitory activity. Most of the dimers displayed enhanced inhibitory activities with micromolar IC50 values lower than that observed for each thiazolone scaffold separately. Moreover, most of these compounds were selective CDC25 inhibitors. Dimer 40 showed an IC 50 value of 2.9 μM and could inhibit CDC25 activity without generating reactive oxygen species which is likely to occur with quinone-based inhibitors. Molecular docking studies suggested that the dimers could bind simultaneously to the active site and the inhibitor binding pocket.
A new approach for the N- and S-galactosylation of 5-arylidene-2-thioxo-4- thiazolidinones
Khodair, Ahmed I.,Gesson, Jean-Pierre
experimental part, p. 2831 - 2837 (2012/01/02)
N- and S-galactosylation was carried out via the reaction of 5-((Z)-arylidene)-2-thioxo-4-thiazolidinones with 2,3,4,6-tetra-O-acetyl- α-d-galactopyranosyl bromide under alkaline conditions or under silylation conditions. Deacetylation of the N-galactosyl
Rhodanine derivatives as novel inhibitors of PDE4
Irvine, Mark W.,Patrick, Graham L.,Kewney, Justin,Hastings, Stuart F.,MacKenzie, Simon J.
, p. 2032 - 2037 (2008/12/21)
The discovery, synthesis and in vitro activity of a novel series of rhodanine based phosphodiesterase-4 (PDE4) inhibitors is described. Structure-activity relationship studies directed toward improving potency led to the development of submicromolar inhibitors 2n and 3i (IC50 = 0.89 & 0.74 μM). The replacement of rhodanine with structurally related heterocycles was also investigated and led to the synthesis of pseudothiohydantoin 7 (IC50 = 0.31 μM).
A practical access to novel 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones via sulfur/nitrogen displacement under solvent-free microwave irradiation
Bourahla, Khadidja,Derdour, A?cha,Rahmouni, Mustapha,Carreaux, Fran?ois,Bazureau, Jean Pierre
, p. 5785 - 5789 (2008/02/09)
A new effective approach to the synthesis of a small library of 2-amino-5-arylidene-1,3-thiazol-4(5H)-ones was reported using solvent-free reaction conditions under microwave irradiation. In the first step, rhodanines were subjected to Knoevenagel condens
Synthesis and antifungal activity of (Z)-5-arylidenerhodanines
Sortino, Maximiliano,Delgado, Paula,Juarez, Sabina,Quiroga, Jairo,Abonia, Rodrigo,Insuasty, Braulio,Nogueras, Manuel,Rodero, Laura,Garibotto, Francisco M.,Enriz, Ricardo D.,Zacchino, Susana A.
, p. 484 - 494 (2008/03/12)
An efficient microwave-assisted synthesis of new (Z)-5-arylidenerhodanines under solvent-free conditions is described and their in vitro antifungal activity was evaluated following the CLSI (formerly NCCLS) guidelines against a panel of both standardized
