52147-97-4Relevant academic research and scientific papers
Highly efficient azido-Ugi multicomponent reactions for the synthesis of bioactive tetrazoles bearing sulfonamide scaffolds
Nazeri, Mohammad Taghi,Nowee, Ali Beygzade,Javanbakht, Siamak,Farhid, Hassan,Shaabani, Ahmad,Notash, Behrouz
, (2021)
Recent studies revealed that the contribution of the different bioactive scaffolds in one structure creates modern drugs/compounds with unique synergistic biological properties. In this regard, thanks to the interesting biological and medicinal properties
Design of Development Candidate eFT226, a First in Class Inhibitor of Eukaryotic Initiation Factor 4A RNA Helicase
Ernst, Justin T.,Thompson, Peggy A.,Nilewski, Christian,Sprengeler, Paul A.,Sperry, Samuel,Packard, Garrick,Michels, Theodore,Xiang, Alan,Tran, Chinh,Wegerski, Christopher J.,Eam, Boreth,Young, Nathan P.,Fish, Sarah,Chen, Joan,Howard, Haleigh,Staunton, Jocelyn,Molter, Jolene,Clarine, Jeff,Nevarez, Andres,Chiang, Gary G.,Appleman, Jim R.,Webster, Kevin R.,Reich, Siegfried H.
supporting information, p. 5879 - 5955 (2020/07/03)
Dysregulation of protein translation is a key driver for the pathogenesis of many cancers. Eukaryotic initiation factor 4A (eIF4A), an ATP-dependent DEAD-box RNA helicase, is a critical component of the eIF4F complex, which regulates cap-dependent protein synthesis. The flavagline class of natural products (i.e., rocaglamide A) has been shown to inhibit protein synthesis by stabilizing a translation-incompetent complex for select messenger RNAs (mRNAs) with eIF4A. Despite showing promising anticancer phenotypes, the development of flavagline derivatives as therapeutic agents has been hampered because of poor drug-like properties as well as synthetic complexity. A focused effort was undertaken utilizing a ligand-based design strategy to identify a chemotype with optimized physicochemical properties. Also, detailed mechanistic studies were undertaken to further elucidate mRNA sequence selectivity, key regulated target genes, and the associated antitumor phenotype. This work led to the design of eFT226 (Zotatifin), a compound with excellent physicochemical properties and significant antitumor activity that supports clinical development.
Antioxidant, Anti-inflammatory, and Neuroprotective Effects of Novel Vinyl Sulfonate Compounds as Nrf2 Activator
Choi, Ji Won,Shin, Su Jeong,Kim, Hyeon Ji,Park, Jong-Hyun,Kim, Hyeon Jeong,Lee, Elijah Hwejin,Pae, Ae Nim,Bahn, Yong Sun,Park, Ki Duk
supporting information, p. 1061 - 1067 (2019/06/24)
The main pathway responsible for cellular regulation against oxidative stress is nuclear factor E2-related factor-2 (Nrf2) signaling. We previously synthesized and reported a novel vinyl sulfone (1) as an Nrf2 activator with therapeutic potential for Parkinson's disease (PD). In this study, we changed the vinyl sulfone to vinyl sulfonamide or vinyl sulfonate to improve Nrf2 activating efficacy. We observed that the introduction of vinyl sulfonamide led to a reduction of the effects on Nrf2 activation, whereas vinyl sulfonate compounds exhibited superior activity compared to the vinyl sulfone compounds. Among the vinyl sulfonates, 3c exhibited 6.9- and 83.5-fold higher effects on Nrf2 activation than the corresponding vinyl sulfone (1) and vinyl sulfonamide (2c), respectively. Compound 3c was confirmed to induce expression of the Nrf2-dependent antioxidant enzymes at the protein level in cells. In addition, 3c mitigated PD-associated behavioral deficits by protecting DAergic neurons in the MPTP-induced mouse model of PD.
NOVEL SUBSTITUTED SULFONYLUREA DERIVATIVES
-
Page/Page column 18, (2019/03/17)
The present invention relates to novel heterocyclic compounds of the general formula (I) their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, diastereomers and polymorphs. The invention also relates to processes for
Green approach for the synthesis of thiophenyl pyrazoles and isoxazoles by adopting 1,3-dipolar cycloaddition methodology and their antimicrobial activity
Sowmya,Lakshmi Teja,Padmaja,Kamala Prasad,Padmavathi
, p. 891 - 898 (2017/12/26)
A variety of N-((1,3-diphenyl-5-aryl-1H-pyrazol-4-yl)sulfonyl)thiophene-2-carboxamides (7) and N-((5-aryl-3-phenylisoxazol-4-yl)sulfonyl)thiophene-2-carboxamides (8) were prepared from (E)-N-(arylethenesulfonyl)thiophene-2-carboxamides (4) adopting 1,3-di
Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes
Wang, Xiaoyang,Liu, Jing,Yu, Ze,Guo, Minjie,Tang, Xiangyang,Wang, Guangwei
supporting information, p. 6516 - 6519 (2018/10/20)
A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroal
EIF4A-INHIBITING COMPOUNDS AND METHODS RELATED THERETO
-
Paragraph 0966; 0967, (2017/08/01)
The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X, Y, R1, R2, R3a, R3b, R4a, R4b and R5 are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4A and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.
Diastereoselective synthesis of novel tetra-and pentacyclic annulated coumarino-δ-sultam pyrrolidine, pyrrolizidine, pyrrolothiazole and isoxazolidine derivatives: Via intramolecular 1,3-dipolar cycloadditions
Ghandi, Mehdi,Zarezadeh, Nahid,Abbasi, Alireza
, p. 67805 - 67816 (2016/08/02)
A facile and efficient strategy towards the novel tetra- and pentacyclic annulated coumarino-δ-sultam pyrrolidine, pyrrolizidine, pyrrolothiazole and isoxazolidine via intramolecular 1,3-dipolar cycloadditions of nitrones or azomethine ylides is described
Solvent-free synthesis of novel styrenesulfonamide derivatives and evaluation of their antibacterial activity
Maghsoodi, Narjes Khaton,Khazaeli, Tooba,Massah, Ahmad Reza
, p. 141 - 144 (2015/06/02)
Novel N-aryl-styrenesulfonamide derivatives have been prepared from styrenesulfonyl chloride and a variety of amines under solvent-free conditions and their in vitro anti-bacterial activities against Staphylococcus aureus and Escherichia coli have been de
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
supporting information, 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.
