21875-74-1Relevant academic research and scientific papers
Stevens rearrangement of thioethers with arynes: A facile access to multi-substituted β-keto thioethers
Xu, Xiao-Bo,Lin, Zi-Hua,Liu, Yuyin,Guo, Jian,He, Yun
supporting information, p. 2716 - 2720 (2017/04/03)
An effective method for the synthesis of multi-substituted β-keto thioethers via Stevens rearrangement of simple β-keto thioethers with arynes has been developed. In these reactions, successive C-S/C-H/C-C bonds were formed in one pot under mild and transition-metal free conditions to afford multi-substituted β-keto thioethers in moderate to good yields.
Design, synthesis and biological evaluation of novel (E)-α- benzylsulfonyl chalcone derivatives as potential BRAF inhibitors
Li, Qing-Shan,Li, Cui-Yun,Lu, Xiang,Zhang, Hui,Zhu, Hai-Liang
experimental part, p. 288 - 295 (2012/07/14)
Activating mutations in the BRAF serine/threonine kinase are found in more than 70% of human melanomas, >90% of which are BRAFV600E. It provides new therapeutic opportunities in malignant melanoma. In silico and in vitro screening of our compound collection has identified Hit 2 as BRAF V600E inhibitor. Based on its structure, a series of novel (E)-α-benzylsulfonyl chalcone derivatives (13-40) were designed and synthesized. Compound 38 exhibited the most potent inhibitory activity with an IC50 value of 0.17 μM for BRAFV600E and GI50 value of 0.52 μM for mutant BRAF-dependent cells. The results of cell based pERK activity and cellular selectivity suggested that those compounds could selectively inhibit proliferation of mutant BRAF-dependent melanoma cell line through inhibition of oncogenic BRAF.
Enantioselective synthesis of chiral sulfones by ir-catalyzed asymmetric hydrogenation: A facile approach to the preparation of chiral allylic and homoallylic compounds
Zhou, Taigang,Peters, Byron,Maldonado, Matias F.,Govender, Thavendran,Andersson, Pher G.
supporting information; experimental part, p. 13592 - 13595 (2012/10/08)
A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Baecklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%).
One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction
Zhdanko, Alexander G.,Gulevich, Anton V.,Nenajdenko, Valentine G.
experimental part, p. 4692 - 4702 (2009/10/02)
Fully protected natural and unnatural N-acetylcysteine, dipeptide Cys-Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2,2,2-Trifluoroethanol was shown to be a superior reaction media than methanol in some reactions. Also, the 4-methyl-2,6,7-trioxabicyclo[2.2.2]octyl derivative (OBO-ester) of isocyanoacetic acid was shown to be superior to use than ethyl isocyanoacetate as a peptide synthesis precursor in cases when higher reactivity of an isocyanide is required.
Photoreactions of β-Ketosulphides: Aryl and Benzyl Phenacyl Sulphides and Related Compounds
Arora, Kanwar J. S.,Collier, John R.,Deodhar, Dinker J.,Hesabi, Masoud-M.,Hill, John
, p. 2148 - 2183 (2007/10/02)
Photoreactions of aryl phenacyl sulphides were studied, particularly in regard to substituent and solvent effects.In general, aryl phenacyl sulphides Ar1SCH2COAr2 1 = p-tolyl, Ar2 = p-X-C6H4 (X = H, Cl, OH, OMe, and Ph), 2-thienyl, and 2-furyl; Ar1 = 2,4,6-trimethylphenyl, Ar2 = Ph and p-HOC6H4; Ar1 = 2-benzthiazolyl, Ar2 = Ph> underwent photochemical cleavage to disulphides (Ar1S)2 and ketones Ar2COMe.In a few cases a diketone (Ar2COCH2)2 was the only, or major, carbonyl photoproduct.Similar photochemical behaviour was shown by ketosulphides p-Me-C6H4SCH(R)COPh (R = PhCH2, PhCOCH2, and p-Me-C6H4S) and related acetophenone derivatives PhCOCH2SR (R = COPh, SO3Na, and SCH2COPh).In a few instances, from p-Me-C6H4SCH2COAr (Ar = Ph, p-Cl-C6H4, and p-Ph-C6H4), a minor photoproduct was a 2-aryl-5-methylbenzothiophen.Benzyl phenacyl sulphides p-X-C6H4COCH2SCH2Ph (X = OH and OMe) also underwent photo-cleavage to give dibenzyl disulphide and a ketone.Free-radical cleavage products ArCOCH2(.) (Ar = Ph and p-MeO-C6H4) and p-Me-C6H4S(.) were trapped as adducts p-Me-C6H4SC(Ph)2CH2CH2COAr when irradiation of the ketosulphide was carried out in the presence of 1,1-diphenylethylene. 2,5-Diphenylfuran was formed photochemically from 1,4-diphenylbutane-1,4-dione on irradiation in methanol.
METHYLENATION WITH PHOSPHONATE ESTERS
Fox, Marye Anne,Triebel, Carol A.,Rogers, Ralph
, p. 1055 - 1062 (2007/10/02)
A series of 2-aryl-1-thioalkyl-2-propenes have been synthesized by treating the corresponding thioalkylated acetophenones with the anion of methyl phosphonate.
