936644-39-2Relevant articles and documents
Switchable Divergent Synthesis in Gold-Catalyzed Difunctionalizations of o-Alkynylbenzenesulfonamides with Aryldiazonium Salts
Li, Jun,Shi, Hongwei,Zhang, Shan,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 7713 - 7717 (2021/10/20)
Gold-catalyzed difunctionalizations of o-alkynylbenzenesulfonamides with aryldiazonium salts are reported herein. Upon irradiation with the blue LEDs, benzosultam products were formed via aminoarylation accompanied by the release of N2. Without irradiatio
Sulfonamido carboranes as highly selective inhibitors of cancer-specific carbonic anhydrase IX
Das, Viswanath,El Anwar, Suzan,Holub, Josef,Kugler, Michael,Nekvinda, Jan,?ezá?ová, Pavlína,?ícha, Václav,Brynda, Ji?í,D?ubák, Petr,Dvo?anová, Jana,Fábry, Milan,Grüner, Bohumír,Gurská, Soňa,Hajdúch, Marián,Havránek, Miroslav,Král, Vlastimil,Li?ková, Barbora,Matějková, Stanislava,Medvedíková, Martina,Pospí?ilová, Klára
supporting information, (2020/06/08)
Carbonic anhydrase IX (CA IX) is a transmembrane enzyme overexpressed in hypoxic tumors, where it plays an important role in tumor progression. Specific CA IX inhibitors potentially could serve as anti-cancer drugs. We designed a series of sulfonamide inhibitors containing carborane clusters based on prior structural knowledge of carborane binding into the enzyme active site. Two types of carborane clusters, 12-vertex dicarba-closo-dodecaborane and 11-vertex 7,8-dicarba-nido-undecaborate (dicarbollide), were connected to a sulfonamide moiety via aliphatic linkers of varying lengths (1–4 carbon atoms; n = 1–4). In vitro testing of CA inhibitory potencies revealed that the optimal linker length for selective inhibition of CA IX was n = 3. A 1-sulfamidopropyl-1,2-dicarba-closo-dodecaborane (3) emerged as the strongest CA IX inhibitor from this series, with a Ki value of 0.5 nM and roughly 1230-fold selectivity towards CA IX over CA II. X-ray studies of 3 yielded structural insights into their binding modes within the CA IX active site. Compound 3 exhibited moderate cytotoxicity against cancer cell lines and primary cell lines in 2D cultures. Cytotoxicity towards multicellular spheroids was also observed. Moreover, 3 significantly lowered the amount of CA IX on the cell surface both in 2D cultures and spheroids and facilitated penetration of doxorubicin. Although 3 had only a moderate effect on tumor size in mice, we observed favorable ADME properties and pharmacokinetics in mice, and preferential presence in brain over serum.
Small-molecule fluorophores with large stokes shifts: 9-iminopyronin analogues as clickable tags
Horváth, Peter,?ebej, Peter,?olomek, Tomá?,Klán, Petr
, p. 1299 - 1311 (2015/02/19)
The design, synthesis, and both experimental and theoretical studies of several novel 9-(acylimino)- and 9-(sulfonylimino)pyronin derivatives containing either an oxygen or a silicon atom at position 10 are reported. These compounds, especially the Si analogues, exhibit remarkably large Stokes shifts (around 200 nm) while still possessing a high fluorophore brightness, absorption bands in the near-UV and visible part of the spectrum, and high thermal and photochemical stabilities in protic solvents. The reason for the observed large Stokes shifts is an intramolecular charge-transfer excitation of an electron from the HOMO to the LUMO of the chromophore, accompanied by elongation of the C9-N bond and considerable solvent reorganization due to hydrogen bonding to the solvent. Due to the photophysical properties of the studied compounds and their facile and high-yielding synthesis, as well as a simple protocol for their bioorthogonal ligation to a model saccharide using a Huisgen alkyne-azide cycloaddition, they represent excellent candidates for biochemical and biological applications as fluorescent tags and indicators for multichannel imaging. 9-(Acylimino)pyronins alter their optical properties upon protonation and may also be used as pH sensors.
The use of a [4 + 2] cycloaddition reaction for the preparation of a series of 'tethered' Ru(ii)-diamine and aminoalcohol complexes
Cheung, Fung Kei,Hayes, Aidan M.,Morris, David J.,Wills, Martin
, p. 1093 - 1103 (2008/01/01)
A series of catalysts have been prepared for use in the asymmetric transfer hydrogenation of ketones. The complexes were prepared using a [4 + 2] cycloaddition reaction at a key step in the reaction sequence. This provides a means for the synthesis of cat