4392-54-5Relevant articles and documents
Novel benzenesulfonamides aryl and arylsulfone conjugates adopting tail/dual tail approaches: Synthesis, carbonic anhydrase inhibitory activity and molecular modeling studies
Eldeeb, Assem H.,Abo-Ashour, Mahmoud F.,Angeli, Andrea,Bonardi, Alessandro,Lasheen, Deena S.,Elrazaz, Eman Z.,Nocentini, Alessio,Gratteri, Paola,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
supporting information, (2021/05/10)
New series of benzenesulfonamide and benzoic acid derivatives were designed and synthesized using tail/dual tail approach to improve potency and selectivity as carbonic anhydrase inhibitors. The synthesized compounds evaluated as CAIs against isoforms hCA I, II, IV and IX with acetazolamide (AAZ) as standard inhibitor. The benzenesulfonamide derivatives 7a-d, 8a-h, 12a-c, 13a and 15a-c showed moderate to potent inhibitory activity with selectivity toward isoform hCA II, especially, compound 13a with (Ki = 7.6 nM), while the benzoic acid analogues 12d-f, 13b and 15d-f didn't show any activity except compounds 12d,f and 15e that showed weak activity. Additionally, molecular docking was performed for compounds 7a, 8a, 8e, 12a, 13a and 15a on isoform hCA I, II to illustrate the possible interaction with the active site to justify the inhibitory activity.
One-Pot Synthesis of Indoles and Pyrazoles via Pd-Catalyzed Couplings/Cyclizations Enabled by Aqueous Micellar Catalysis
Akporji, Nnamdi,Braga, Felipe C.,Gabriel, Christopher M.,Landstrom, Evan B.,Lee, Nicholas R.,Lipshutz, Bruce H.
supporting information, (2020/09/02)
An effective one-pot synthesis of either indoles or pyrazoles can be achieved via Pd-catalyzed aminations followed by subsequent cyclizations facilitated by aqueous micellar catalysis. This new technology includes efficient couplings with low loadings of palladium, a more stable source of the required hydrazine moiety, greater atom economy for the initial coupling, and reduced reaction temperatures, all leading to environmentally responsible processes.
3-Hydrazinoisatin-based benzenesulfonamides as novel carbonic anhydrase inhibitors endowed with anticancer activity: Synthesis, in vitro biological evaluation and in silico insights
Abo-Ashour, Mahmoud F.,Eldehna, Wagdy M.,Nocentini, Alessio,Bonardi, Alessandro,Bua, Silvia,Ibrahim, Hany S.,Elaasser, Mahmoud M.,Kry?tof, Vladimír,Jorda, Radek,Gratteri, Paola,Abou-Seri, Sahar M.,Supuran, Claudiu T.
, (2019/10/19)
Herein we describe the design and synthesis of two series of sulfonamides featuring N-unsubstituted (4a-c) or N-substituted (7a-o) isatin moieties (as tails) connected to benzenesulfonamide moiety via a hydrazine linker. All the prepared sulfonamides (4a-c and 7a-o) showed potent inhibitory activities toward transmembrane tumor-associated human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, IX and XII with KI range (8.3–65.4 nM) and (11.9–72.9 nM), respectively. Furthermore, six sulfonamides (7e, 7i, 7j, 7m, 7n and 7o) were assessed for their anti-proliferative activity, according to US-NCI protocol, toward a panel of sixty cancer cell lines. Compounds 7j and 7n were the most promising counterparts in this assay displaying broad spectrum anti-proliferative activity toward diverse cell lines. Also, sulfonamide 7n significantly inhibited clonogenicity of HCT-116 cells in a concentration dependent manner in the colony forming assay. Moreover, molecular modeling studies were performed to gain insights for the plausible binding interactions and affinities for the target isatin-based sulfonamides (4a-c and 7a-o) within hCA isoforms II and IX active sites.
Virtual ligand screening of the p300/CBP histone acetyltransferase: Identification of a selective small molecule inhibitor
Bowers, Erin M.,Yan, Gai,Mukherjee, Chandrani,Orry, Andrew,Wang, Ling,Holbert, Marc A.,Crump, Nicholas T.,Hazzalin, Catherine A.,Liszczak, Glen,Yuan, Hua,Larocca, Cecilia,Saldanha, S. Adrian,Abagyan, Ruben,Sun, Yan,Meyers, David J.,Marmorstein, Ronen,Mahadevan, Louis C.,Alani, Rhoda M.,Cole, Philip A.
scheme or table, p. 471 - 482 (2011/08/06)
The histone acetyltransferase (HAT) p300/CBP is a transcriptional coactivator implicated in many gene regulatory pathways and protein acetylation events. Although p300 inhibitors have been reported, a potent, selective, and readily available active-sitedirected small molecule inhibitor is not yet known. Here we use a structure-based, in silico screening approach to identify a commercially available pyrazolone- containing small molecule p300 HAT inhibitor, C646. C646 is a competitive p300 inhibitor with a Ki of 400 nM and is selective versus other acetyltransferases. Studies on site-directed p300 HAT mutants and synthetic modifications of C646 confirm the importance of predicted interactions in conferring potency. Inhibition of histone acetylation and cell growth by C646 in cells validate its utility as a pharmacologic probe and suggest that p300/CBP HAT is a worthy anticancer target.
Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating hydrazino moieties
Winum, Jean-Yves,Dogné, Jean-Michel,Casini, Angela,De Leval, Xavier,Montero, Jean-Louis,Scozzafava, Andrea,Vullo, Daniela,Innocenti, Alessio,Supuran, Claudiu T.
, p. 2121 - 2125 (2007/10/03)
Targeting proteins overexpressed in hypoxic tumors is as an important means of controlling cancer disease. One such protein is the carbonic anhydrase (CA) isoenzyme IX, which in some types of tumors is overexpressed 150-200-fold. We report here a series of sulfonamide derivatives, prepared from 2-carbohydrazido- and 4-carbohydrazido-benzenesulfonamides, which were further derivatized by reaction with aryl isocyanates or arylsulfonyl isocyanates. Several low nanomolar CA IX inhibitors were detected in this way. SAR is discussed for the diverse types of inhibitors and their affinity for different isozymes, with the aim of obtaining isozyme-specific CA IX inhibitors, with putative applications as antitumor drugs.
Synthesis of 4-(1,4-diaryl-2H-cyclopent[d]pyridazin-2-yl) benzenesulfonamides
Blankenbuehler, Mark,Parkin, Sean
, p. 2383 - 2391 (2007/10/03)
The condensation of cyclopentadienyl-derived γ-diketones and arylhydrazines was utilized to synthesize 4-(1,4-diphenyl-2H-cyclopent[d]- pyridazin-2-yl)benzenesulfonamide and 4-(1,4-di-(4-methylphenyl)-2H-cyclopent[d]pyridazin-2-yl)benzenesulfonamide in better than 80% yield. The crystal structures of the precursor hydroxyfulvene, {(5Z)-5-[hydroxy(4-methylphenyl)- methylene]cyclopenta-1,3-dien-1-yl}(4-methylphenyl)methanone, and the derived pyridazine 4-(1,4-diphenyl-2H-cyclopent[d]pyridazin-2-yl)benzenesulfonamide, were also obtained.
Iron-complexed formazan dyes for polyamide and protein substrates
-
, (2008/06/13)
A family of 1:2 Fe-complexed formazan dyes is described. The dyes unexpectedly afford reddish-violet, violet, blue and black shades on natural and synthetic substrates. Methods for synthesizing the dyes and for dyeing a substrate are described. The dyes represent environmentally friendly alternatives to conventional Cr- and Co-based azo and formazan dyes.
Synthesis of 3-Methyl-1-Phenyl-5-Pyrazolones Containing Arylaminosulfonyl Groups
Lisitsyn, V. N.,Sazonchik, O. B.
, p. 780 - 784 (2007/10/02)
N-Aryl-substituted 3(4)-aminobenzenesulfonamides were synthesized.They are the starting compounds for the production of the corresponding substituted 3(4)-(3-methyl-5-oxo-2-pyrazolin-1-yl)-N-phenylbenzenesulfonamides.Data from the IR, PMR, and mass spectra are presented, and the fragmentation of the molecules is discussed.
