111983-37-0Relevant academic research and scientific papers
Fluoride-Triggered Ring-Opening of Photochromic Diarylpyrans into Merocyanine Dyes: Naked-Eye Sensing in Subppm Levels
Mukhopadhyay, Arindam,Maka, Vijay Kumar,Moorthy, Jarugu Narasimha
, p. 7741 - 7750 (2016)
The fluoride-mediated desilylation reaction has been exploited, for the first time, to trigger ring-opening of photochromic diarylbenzo-/naphthopyrans into highly colored anionic merocyanine dyes with high molar absorptivities to permit naked-eye sensing.
SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride–Amine Adducts
Wang, Hua,Zhou, Feng,Ren, Gerui,Zheng, Qinheng,Chen, Hongli,Gao, Bing,Klivansky, Liana,Liu, Yi,Wu, Bin,Xu, Qingfeng,Lu, Jianmei,Sharpless, K. Barry,Wu, Peng
, p. 11203 - 11208 (2017)
The SuFEx-based polycondensation between bisalkylsulfonyl fluorides (AA monomers) and bisphenol bis(t-butyldimethylsilyl) ethers (BB monomers) using [Ph3P=N?PPh3]+[HF2]? as the catalyst is described.
SuFEx-based synthesis of polysulfates
Dong, Jiajia,Sharpless, K. Barry,Kwisnek, Luke,Oakdale, James S.,Fokin, Valery V.
supporting information, p. 9466 - 9470 (2014/11/07)
High-molecular-weight polysulfates are readily formed from aromatic bis(silyl ethers) and bis(fluorosulfates) in the presence of a base catalyst. The reaction is fast and proceeds well under neat conditions or in solvents, such as dimethyl formamide or N-methylpyrrolidone, to provide the desired polymers in nearly quantitative yield. These polymers are more resistant to chemical degradation than their polycarbonate analogues and exhibit excellent mechanical, optical, and oxygen-barrier properties. High-molecular-weight polysulfates are readily formed from aromatic bis(silyl ethers) and bis(fluorosulfates) in the presence of a base catalyst. The polymers were obtained in nearly quantitative yield under neat conditions, they are more resistant to chemical degradation than their polycarbonate analogues and exhibit excellent mechanical, optical, and oxygen-barrier properties. BPA=bisphenol A.
Synthesis, in vitro and in vivo activity of benzophenone-based inhibitors of steroid sulfatase
Hejaz, Hatem A. M.,Woo, L. W. Lawrence,Purohit, Atul,Reed, Michael J.,Potter, Barry V. L.
, p. 2759 - 2772 (2007/10/03)
Steroid sulfatase (STS) is an important new therapeutic target in oncology. Attempts to design nonsteroidal STS inhibitors, because of the oestrogenicity of the original lead oestrone 3-O-sulfamate in rodents, have led to the discovery of benzophenone-4,4′-O,O-bis-sulfamate (BENZOMATE, 3). The nonfused bicyclic BENZOMATE is a highly potent STS inhibitor in vitro, inhibiting STS activity in intact MCF-7 breast cancer cells by >70% at 0.1μM and in placental microsomes by >98% at 10μM. When MCF-7 cells were pre-treated with 3 at 1μM and then washed to remove unbound inhibitor, the initial 94% inhibition was reduced to 89% suggesting that 3, like other sulfamate-based STS inhibitors, inhibits the enzyme irreversibly. This agent also inhibits rat liver STS activity by 84% and 93% respectively 24h after a single dose of 1 or 10mg/kg, demonstrating that BENZOMATE possesses similar in vivo potency to the established potent nonsteroidal inhibitor 667COUMATE. Several modifications were made to BENZOMATE structurally and effects on in vitro activity were examined. These structure-activity relationship studies show that its carbonyl and bis-sulfamate groups are pivotal for activity, although conformational flexibility is not required. Two rigid anthraquinone-based sulfamate derivatives however showed inhibitory activity significantly better than BENZOMATE in the MCF-7 cell assay. BENZOMATE and related analogues therefore represent an important class of non-steroidal STS inhibitor and lead compounds for future drug design.
