21626-69-7Relevant academic research and scientific papers
Ammonium chloride-catalyzed four-component sonochemical synthesis of novel hexahydroquinolines bearing a sulfonamide moiety
Hussein
, p. 54 - 64 (2015)
Ammonium chloride as a very inexpensive and readily available reagent efficiently catalyzes one-pot four-component condensation of dimedone with aromatic aldehyde, malononitrile or ethyl cyanoacetate, and sulfonamide derivatives in ethanol at 70°C under ultrasonic irradiation to afford the corresponding 2-amino-4-aryl-1,4,5,6,7,8-hexahydroquinolines bearing a sulfonamide moiety in high yields. In comparison to conventional methods, high yields, easy work-up, and short reaction time are advantages of this sonochemical procedure. The effects of the catalyst, solvent, and temperature are assessed.
Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors
Uysal, Sirin,Soyer, Zeynep,Saylam, Merve,Tarikogullari, Ayse H.,Yilmaz, Sinem,Kirmizibayrak, Petek Ballar
, (2020/10/12)
A series of novel 4-aminobenzensulfonamide/carboxamide derivatives bearing naphthoquinone pharmacophore were designed, sythesized and evaluated for their proteasome inhibitory and antiproliferative activities against human breast cancer cell line (MCF-7). The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The proteasome inhibitory activity studies were carried out using cell-based assay. The antiproteasomal activity results revealed that most of the compounds exhibited inhibitory activity with different percentages against the caspase-like (C-L, β1 subunit), trypsin-like (T-L, β2 subunit) and chymotrypsin-like (ChT-L, β5 subunit) activities of proteasome. Among the tested compounds, compound 14 bearing 5-chloro-2-pyridyl ring on the nitrogen atom of sulfonamide group is the most active compound in the series and displayed higher inhibition with IC50 values of 9.90 ± 0.61, 44.83 ± 4.23 and 22.27 ± 0.15 μM against ChT-L, C-L and T-L activities of proteasome compared to the lead compound PI-083 (IC50 = 12.47 ± 0.21, 53.12 ± 2.56 and 26.37 ± 0.5 μM), respectively. The antiproliferative activity was also determined by MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay in vitro. According to the antiproliferative activity results, all of the compounds exhibited cell growth inhibitory activity in a range of IC50 = 1.72 ± 0.14–20.8 ± 0.5 μM and compounds 13 and 28 were found to be the most active compounds with IC50 values of 1.79 ± 0.21 and 1.72 ± 0.14 μM, respectively. Furthermore, molecular modeling studies were carried out for the compounds 13, 14 and 28 to investigate the ligand-enzyme binding interactions.
Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source
Li, Wanfang,Beller, Matthias,Wu, Xiao-Feng
supporting information, p. 9513 - 9516 (2014/08/18)
Various sulfonamides have been synthesized from triazenes and sulfur dioxide. In the presence of just a catalytic amount of BF3· OEt2, a series of 1-aryl-triazenes were converted into sulfonyl hydrazines in good to excellent yields. When using CuCl2 as the catalyst, the corresponding sulfonamides can be produced from the 1-aryl triazenes in good yields. This journal is the Partner Organisations 2014.
Synthesis and pharmacological evaluation of N-phenyl-acetamide sulfonamides designed as novel non-hepatotoxic analgesic candidates
de Castro Barbosa, Maria Leticia,de Albuquerque Melo, Gabriela Muniz,da Silva, Yolanda Karla Cupertino,de Oliveira Lopes, Raquel,de Souza, Everton Tenorio,de Queiroz, Aline Cavalcanti,Smaniotto, Salete,Alexandre-Moreira, Magna Suzana,Barreiro, Eliezer J.,Lima, Lidia Moreira
experimental part, p. 3612 - 3620 (2009/12/09)
In this paper we report the design, synthesis and pharmacological evaluation of a series of N-phenyl-acetamide sulfonamide derivatives (5a-g), planned by structural modification on the prototype paracetamol (1). In this series (5a-g), compound LASSBio-1300 (5e; ID50 = 5.81 μmol/kg) stands out as a new non-hepatotoxic analgesic drug candidate. The increase of area, volume and eletrostatic potential of paracetamol's analogues seems to be beneficial to the analgesic activity. Unlike paracetamol (1) and the other analogues (5a, 5d-g), compounds 5b and 5c presented an important anti-hypernociceptive activity associated to inflammatory pain.
NOVEL ADENOSINE A3 RECEPTOR AGONISTS
-
Page/Page column 28, (2008/06/13)
The invention realizes that a series of sulfonamido derivatives with a conserved uronamide group at the 5' position provide superior A3 receptor affinity as well as selectivity. These new adenosine agonists are sulfonamido deritatives N-substituted with aliphatic groups (cyclic or linear) or aromatic radicals.
