740835-10-3Relevant academic research and scientific papers
Synthesis and evaluation of antiepileptic activity of newly designed coumarin-sulfonamide hybrids
Dhiman, Neerupma,Gupta, Arti,Kumar, Sandeep,Mallikarjun, B. P.,Sharma, Archana,Singh, Vijay Kumar
, p. 3108 - 3114 (2021/12/14)
The combination of different heterocyclic rings to form a multifunctional compound is a new approach to get the potent and selective compounds, which can act as antiepileptic drugs. In this study we designed and synthesized the hybrid of the coumarin ring with sulfonamide moiety. Coumarin sulfonamide hybrids (CS1-CS7) were synthesized by Knoevenagel condensation of methyl anilinosulfonyl acetate with substituted salicyaldehyde in the presence of catalytic base. The synthesized hybrid compounds were characterized by means of mass, 1H & 13C NMR and FTIR spectroscopy, moreover antiepileptic activity was screened through seizure model of epilepsy using pentylenetetrazole and maximal electroshock. According to results, compound CS-2 remained to be highest potent and presented significant protection at 60 mg/kg in both the seizure models. Furthermore, compound CS-2 was also evaluated for biochemical and a histopathological study in which no significant results were obtained. In addition to former activities, compound CS-2 was also examined for liver toxicity.
Design, synthesis, and biological evaluation of (E)-N-Aryl-2- arylethenesulfonamide analogues as potent and orally bioavailable microtubule-targeted anticancer agents
Reddy, M. V. Ramana,Mallireddigari, Muralidhar R.,Pallela, Venkat R.,Cosenza, Stephen C.,Billa, Vinay K.,Akula, Balaiah,Subbaiah, D. R. C. Venkata,Bharathi, E. Vijaya,Padgaonkar, Amol,Lv, Hua,Gallo, James M.,Reddy, E. Premkumar
, p. 5562 - 5586 (2013/07/26)
A series of novel (E)-N-aryl-2-arylethenesulfonamides (6) were synthesized and evaluated for their anticancer activity. Some of the compounds in this series showed potent cytotoxicity against a wide spectrum of cancer cell-lines (IC50 values ranging from 5 to 10 nM) including all drug resistant cell-lines. Nude mice xenograft assays with compound (E)-N-(3-amino-4- methoxyphenyl)-2-(2′,4′,6′-trimethoxyphenyl)ethenesulfonamide (6t) showed dramatic reduction in tumor size, indicating their in vivo potential as anticancer agents. A preliminary drug development study with compound 6t is predicted to have increased blood-brain barrier permeability relative to many clinically used antimitotic agents. Mechanistic studies indicate that 6t and some other analogues disrupted microtubule formation, formation of mitotic spindles, and arrest of cells in mitotic phase. Compound 6t inhibited purified tubulin polymerization in vitro and in vivo and circumvented drug resistance mediated by P-glycoprotein. Compound 6t specifically competed with colchicine binding to tubulin and with similar avidity as podophylltoxin, indicating its binding site on tubulin.
Synthesis of new coumarin 3-(N-aryl) sulfonamides and their anticancer activity
Reddy, Natala Srinivasa,Mallireddigari, Muralidhar Reddy,Cosenza, Stephen,Gumireddy, Kiranmai,Bell, Stanley C.,Reddy, E. Premkumar,Reddy, M.V. Ramana
, p. 4093 - 4097 (2007/10/03)
Synthesis of coumarin 3-(N-aryl) sulfonamides was accomplished either by Knoevenagel condensation of anilinosulfonylacetic acids with suitable salicylaldehydes or by the reaction of methyl anilinosulfonylacetates with substituted salicylaldehydes in presence of a catalytic amount of a base. All the compounds tested for antiproliferative activity in different cancer cell lines have shown GI50 values less than 100μM.
