121-61-9Relevant articles and documents
Photochemical C?H Amination of Ethers and Geminal Difunctionalization Reactions in One Pot
Hernández-Guerra, Daniel,Hlava?ková, Anna,Pramthaisong, Chiranan,Vespoli, Ilaria,Pohl, Radek,Slanina, Tomá?,Jahn, Ullrich
, p. 12440 - 12445 (2019)
A mild, atom-economic, and metal-free α-C?H amination of ethers using relatively stable nonafluorobutanesulfonyl (nonaflyl, Nf) azide as the aminating reagent to give N-sulfonyl hemiaminals is reported. This enables unprecedented C(sp3) difunctionalization reactions, leading to diverse functionalized amino group containing compounds starting from simple ethers in one pot.
Two New Diazonium Bis(perfluoroalkyl)arylsulfonyl Imide Zwitterionic Monomers from Perfluoro(3-oxa-4-pentene)sulfonyl Fluoride for Proton Exchange Membrane Fuel Cells
Mei, Hua,Ibrahim, Faisal
, p. 46 - 51 (2017)
Two new bis(perfluoroalkyl)arylsulfonyl imide monomers, which contain the aryl diazonium moiety and intramolecular zwitterionic fragment, have been designed and prepared for the first time from perfluoro(3-oxa-4-pentene)sulfonyl fluoride. As promising monomer candidates for high-performance proton exchange membrane fuel cell electrolytes, these two monomers have furnished perfluorinated electrolytes that include the polymers from perfluorinated sulfonic acid or perfluorinated sulfonimide monomers. The synthesis strategies and NMR analysis are summarized and discussed in details.
In situ formation of vilsmeier reagents mediated by oxalyl chloride: A tool for the selective synthesis of N-sulfonylformamidines
Gazvoda, Martin,Kocevar, Marijan,Polanc, Slovenko
, p. 5381 - 5386 (2013)
N-Sulfonylformamidines were produced from sulfonamides or N-acylated sulfonamides using Vilsmeier reagent obtained in situ from N,N-disubstituted formamides and oxalyl chloride. Optically active substrates did not racemize during the process. The efficient and mild cleavage of N-sulfonylformamidines can be achieved with hydrazine hydrate in ethanol. The entire procedure constitutes a simple method for protecting, and deprotecting, the sulfonamide moiety. A straightforward and efficient synthesis for N-sulfonylformamidines by employment of various Vilsmeier reagents generated in situ is described. The reactions proceed under mild reaction conditions and tolerate several sensitive functional groups. Copyright
Novel stereoselective 2,3-disubstituted quinazoline-4(3H)-one derivatives derived from glycine as a potent antimalarial lead
Patel, Tarosh S.,Vanparia, Satish F.,Gandhi, Sahaj A.,Patel, Urmila H.,Dixit, Ritu B.,Chudasama, Chaitanya J.,Dixit, Bharat C.
, p. 8638 - 8649 (2015)
An optimization and modification of Grimmel's method leading to cyclization and incorporation of glycine linked sulphonamide at position-2 in 4-quinazolin-(3H)-ones was accomplished. Generation of a lipophilic site at position-3 of 4-quinazolinones was explored by synthesis of imines, unfortunately leading to an isomeric mixture of stereoisomers. These stereoisomeric mixtures were further converted to a single isomer utilizing the novel methodology developed by the use of an aprotic solvent system. Moreover, a mixture of (Z)/(E)-isomers and single configuration was identified and ascertained using NMR, HMQC, HMBC and NOESY spectroscopic techniques. The synthesized entities were further screened for their antimalarial efficacy pertaining two active scaffolds 8m and 8s. The active molecules were sent forth for enzyme inhibitory study against presumed receptors h-DHFR and Pf-DHFR computationally as well as in vitro, proving their potency as dihydrofolate reductase inhibitors. The oral bioavailability of these active molecules was also predicted by the study of ADME properties, indicating good bioavailability of the active entities.
Condensation reactions of trifluoronitrosomethane CF3NO with sulfanilamide H2NC6H4SO2NH2 - Preparation of CF3NNC6H4SO2NH2, CF3NNC6H4SO2NNCF3, CH3C(O)N(H)C6H4SO2NNCF3
Minkwitz, Rolf,Jakob, Jens,Winter, Andreas
, p. 647 - 654 (1997)
We report the condensations of trifluoronitrosomethane with sulfanilamide. The new compounds p-trifluoromethylazophenylsulfonamide CF3NNC6H4SO2NH2, p-trifluoromethylazosulfonyltrifluoromethylazobenzole CF3NNC6H4SO2NNCF3 and p-trifluoromethylazosulfonyl-acetanilide CH3C(O)N(H)C6H4SO2NNCF3 were characterized by elemental analysis, IR, Raman, mass, 1H, 19F and 13C NMR spectroscopy. In addition we present our approach to the preparation of p-trifluoromethylazosulfonylaniline H2NC6H4SO2NNCF3 by using protecting groups for the amino group.
Switching on prodrugs using radiotherapy
Geng, Jin,Zhang, Yichuan,Gao, Quan,Neumann, Kevin,Dong, Hua,Porter, Hamish,Potter, Mark,Ren, Hua,Argyle, David,Bradley, Mark
, p. 805 - 810 (2021)
Chemotherapy is a powerful tool in the armoury against cancer, but it is fraught with problems due to its global systemic toxicity. Here we report the proof of concept of a chemistry-based strategy, whereby gamma/X-ray irradiation mediates the activation of a cancer prodrug, thereby enabling simultaneous chemo-radiotherapy with radiotherapy locally activating a prodrug. In an initial demonstration, we show the activation of a fluorescent probe using this approach. Expanding on this, we show how sulfonyl azide- and phenyl azide-caged prodrugs of pazopanib and doxorubicin can be liberated using clinically relevant doses of ionizing radiation. This strategy is different to conventional chemo-radiotherapy radiation, where chemo-sensitization of the cancer takes place so that subsequent radiotherapy is more effective. This approach could enable site-directed chemotherapy, rather than systemic chemotherapy, with ‘real time’ drug decaging at the tumour site. As such, it opens up a new era in targeted and directed chemotherapy. [Figure not available: see fulltext.].
Intensified Crystallization Processes for 1:1 Drug-Drug Cocrystals of Sulfathiazole-Theophylline, and Sulfathiazole-Sulfanilamide
Yeh, Kuan Lin,Lee, Tu
, p. 1339 - 1349 (2018)
The chemical synthesis and crystallization steps were integrated successfully for directly producing a 1:1 cocrystal of sulfathiazole-theophylline and a 1:1 cocrystal of sulfathiazole-sulfanilamide. The benefits of this process intensification were the reduction of number of steps, and the amount of energy consumption and solvent used. In addition, the overall cocrystal yields by Intensified Method I were much higher than the ones by the conventional method. Intensified Method I also gave high-purity cocrystals of ≥99%. Sulfathiazole not forming cocrystals with sulfanilamide by Intensified Method I was dissolved in the mother liquor by taking advantage of the pH-dependent solubility of sulfathiazole. Cocrystals of both sulfathiazole-theophylline and sulfathiazole-sulfanilamide systems remained stable under conditions of 40 °C and 75% relative humidity for a month.
Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets
Li, Tingting,Xu, Bo
supporting information, p. 2673 - 2678 (2021/08/03)
Main observation and conclusion: We describe a practical and general protocol for immobilization of heterogeneous catalysts to mechanically robust porous ultra-high molecular weight polyethylene tablets using inter-facial Lifshitz-van der Waals Interactions. Diverse types of powderous catalysts, including Cu, Pd/C, Pd/Al2O3, Pt/C, and Rh/C have been immobilized successfully. The immobilized catalysts are mechanistically robust towards stirring in solutions, and they worked well in diverse synthetic reactions. The immobilized catalyst tablets are easy to handle and reused. Moreover, the metal leaching of immobilized catalysts was reduced significantly.
Inhibition of carbonic anhydrase II by sulfonamide derivatives
Xuan,Zhan,Zhang,Li,Zheng
, p. 412 - 415 (2021/11/22)
A series of sulfonamide derivatives were synthesized, and the enzyme inhibitory activity of the synthesized compounds on carbonic anhydrase II was evaluated. Through molecular docking studies, it was found that compounds 1b, 1e, 2a, 2b, 3a have a strong binding affinity to carbonic anhydrase II. The IC50 values of the four compounds 1e, 2b, 3a, and 3b were lower than that of the positive control drug acetazolamide. What’s more, the compounds had a high inhibitory activity for A549 lung cancer cell growth, among them, 1e and 3a could inhibit both carbonic anhydrase II and lung cancer cell proliferation.
Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture
Kühl, Nikos,Leuthold, Mila M.,Behnam, Mira A. M.,Klein, Christian D.
supporting information, p. 4567 - 4587 (2021/05/06)
The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.
