7778-42-9Relevant articles and documents
Carbonic Anhydrase Glycoinhibitors belonging to the Aminoxysulfonamide Series
Ombouma, Joanna,Vullo, Daniella,Dumy, Pascal,Supuran, Claudiu T.,Winum, Jean-Yves
, p. 819 - 821 (2015)
Abstract A general approach for the synthesis of carbonic anhydrases glycoinhibitors belonging to an aminoxysulfonamide series is presented using a Ferrier sulfonamidoglycosylation reaction on glycals. All the compounds showed good in vitro inhibitory activity against four human carbonic anhydrase isoforms, with selectivity against the cytosolic (hCA II) vs the tumor associated (hCA IX and XII) enzymes.
Uracil-5-yl O-Sulfamate: An Illusive Radiosensitizer. Pitfalls in Modeling the Radiosensitizing Derivatives of Nucleobases
Arthur-Baidoo, Eugene,Chomicz-Mańka, Lidia,Denifl, Stephan,Falkiewicz, Karina,Kozak, Witold,Makurat, Samanta,Rak, Janusz,Rodrigues Costa, Mateus Salomao,Sikorski, Artur,Spisz, Paulina,Wyrzykowski, Dariusz,Zdrowowicz, Magdalena,Ziegler, Patrick
, p. 5600 - 5613 (2020)
Efficient radiotherapy requires the concomitant use of ionizing radiation (IR) and a radiosensitizer. In the present work uracil-5-yl O-sulfamate (SU) is tested against its radiosensitizing potential. The compound possesses appropriate dissociative electron attachment (DEA) characteristics calculated at the M06-2X/6-31++G(d,p) level. Crossed electron-molecular beam experiments in the gas phase demonstrate that SU undergoes efficient DEA processes, and the single C-O or S-O bond dissociations account for the majority of fragments induced by electron attachment. Most DEAs proceed already for electrons with kinetic energies of ～0 eV, which is supported by the exothermic thresholds calculated at the M06-2X/aug-cc-pVTZ level. However, in water solution under reductive conditions and physiological pH, SU does not undergo radiolysis, which demonstrates the crucial influence of aqueous environment on the radiosensitizing properties of modified nucleosides.
Oxidative Allene Amination for the Synthesis of Azetidin-3-ones
Burke, Eileen G.,Schomaker, Jennifer M.
, p. 12097 - 12101 (2015)
Regioselectivity in the aziridination of silyl-substituted homoallenic sulfamates is readily diverted to the distal double bond of the allene to yield endocyclic bicyclic methyleneaziridines with excellent stereocontrol. Subsequent reaction with electrophilic oxygen sources initiates facile rearrangement to densely functionalized, fused azetidin-3-ones in excellent d.r., effectively transferring the axial chirality of the allene to central chirality in the products. The steric nature of the silyl group dictates which of the two rings of the fused azetidin-3-one will undergo further functionalization, providing an additional element of diversity for the preparation of enantioenriched azetidine scaffolds with potential biological activity.
Novel steroid sulfatase inhibitors based on N-thiophosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates
Da?ko, Mateusz,Demkowicz, Sebastian,Biernacki, Karol,Harrous, Amira,Rachon, Janusz,Kozak, Witold,Martyna, Aleksandra,Mas?yk, Maciej,Kubiński, Konrad,Boguszewska-Czubara, Anna
, p. 857 - 866 (2019)
In the present work, we described convenient methods for the synthesis of N-thiophosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates as steroid sulfatase (STS) inhibitors. To design the structures of the potential STS inhibitors, molecular modeling techniques were used. A computational docking method was used to determine the binding modes of the synthesized inhibitors as well as to identify potential interactions between specified functional groups on the inhibitors and the amino acid residues present in the active site of the enzyme. The inhibitory activities of the synthesized compounds were tested in an enzymatic assay with STS isolated from a human placenta. Within the set of newly synthesized compounds, 9e demonstrated the highest inhibitory activity in the enzymatic assay with an IC50 value of 0.201 μM (the IC50 value of 667-COUMATE in the same test was 0.062 μM). Furthermore, we tried to verify if the obtained STS inhibitors are able to pass through the cellular membrane effectively in cell line experiments. In the course of our study, we determined the STS activity in the MCF-7 cell line after incubation in the presence of the inhibitors (at 100 nM concentration). For this evaluation, we included newly synthesized compounds 9a-g and their N-phosphorylated analogs 6a-h, whose synthesis has been previously described. We found that the lowest STS activities were measured in the presence of N-phosphorylated derivatives 6e (0.1% of STS activity) and 6f (0.2% of STS activity). The measured STS activity in the presence of 667-COUMATE (used as a reference) was 0.1%. Moreover, at concentrations up to 1 μM, the most active compounds (6e, 6f, 9b, and 9e) did not exert any toxic effects on zebrafish embryos.
Synthesis of 7-benzylguanosine cap-analogue conjugates for eIF4E targeted degradation
Kaur, Tanpreet,Menon, Arya,Garner, Amanda L.
, p. 339 - 350 (2019)
Eukaryotic translation initiation factor 4E (eIF4E) is a key player in the initiation of cap-dependent translation through recognition of the m7GpppX cap at the 5’ terminus of coding mRNAs. As eIF4E overexpression has been observed in a number of human diseases, most notably cancer, targeting this oncogenic translation initiation factor has emerged as a promising strategy for the development of novel anti-cancer therapeutics. Toward this end, in the present study, we have rationally designed a series of Bn7GxP-based PROTACs for the targeted degradation of eIF4E. Herein we describe our synthetic efforts, in addition to biochemical and cellular characterization of these compounds.
Lewis Base-Br?nsted Acid Co-catalyzed Morita-Baylis-Hillman Reaction of Cyclic Sulfamidate Imines
García Manche?o, Olga,Khassenova, Gaukhar
, p. 2752 - 2755 (2021)
A Lewis base-Br?nsted acid co-catalyzed Morita-Baylis-Hillman reaction of cyclic sulfamidate imines with acrylate-type Michael acceptors has been developed. The combination of equimolecular catalytic amounts of DABCO and acetic acid proved highly efficient and tolerated well a wide range of Michael acceptors and substituted 6-membered ring sulfamidate imines, as well as a sultam derivative. The reaction provides a straightforward access to sulfamidates bearing α,β-unsaturated chains, which allows for the further functionalization of the products. Moreover, the robustness and applicability of the method was demonstrated by performing a gram scale reaction and further functionalization of the MBH-adducts.
Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates
Park, Yunjeong,Lee, Ji Sun,Ryu, Jae-Sang
supporting information, p. 2183 - 2188 (2021/03/15)
An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).
