84885-76-7Relevant academic research and scientific papers
NEW MACROCYCLIC COMPOUNDS, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
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Page/Page column 170; 171, (2021/09/04)
A compound of formula (I) : wherein Z, Y1,Y2,(Formula II)R1 to R7 are as defined in the description, its optical isomers, and addition salts thereof with a pharmaceutically acceptable base. Medicaments.
Rhodium-catalyzed carbonylative coupling of alkyl halides with thiols: a radical process faster than easier nucleophilic substitution
Ai, Han-Jun,Rabeah, Jabor,Brückner, Angelika,Wu, Xiao-Feng
supporting information, p. 1466 - 1469 (2021/02/21)
How to make a carbonylative coupling faster than the easier nucleophilic substitution? In this communication, a rhodium-catalyzed radical-based carbonylative coupling of alkyl halides with thiolphenols has been realized. Thioesters were isolated in good y
Synthesis and structure-activity relationships of soluble 7-substituted 3-(3,5-dimethoxyphenyl)-1,6-naphthyridin-2-amines and related ureas as dual inhibitors of the fibroblast growth factor receptor-1 and vascular endothelial growth factor receptor-2 tyrosine kinases
Thompson, Andrew M.,Delaney, Amy M.,Hamby, James M.,Schroeder, Mel C.,Spoon, Teresa A.,Crean, Sheila M.,Showalter, H. D. Hollis,Denny, William A.
, p. 4628 - 4653 (2007/10/03)
7-Substituted 3-aryl-1,6-naphthyridine-2,7-diamines and related 2-ureas are inhibitors of fibroblast growth factor receptor-1 (FGFR-1) and vascular endothelial growth factor receptor-2 (VEGFR-2). 3-(3,5-Dimethoxyphenyl) and 3-phenyl analogues were prepared from 7-acetamido-2-teri-butylureas by alkylation with benzyl ω-iodoalkyl ethers, debenzylation, and animation, followed by selective cleavage of the 7-N-acetamide. 3-(2,6-Dichlorophenyl) analogues were prepared from the 7-fluoro-2-amine by displacement with substituted alkylamines, followed by selective acylation of the resulting substituted naphthyridine-2,7-diamines with alkyl isocyanates. The 3-(3,5-dimethoxyphenyl) derivatives were low nanomolar inhibitors of both FGFR and VEGFR and were highly selective (>100-fold) over PDGFR and c-Src. Variations in the base strength or spatial position of the 7-side chain base had only small effects on the potency (5-fold) or selectivity (20-fold). The 3-(2,6-dichlorophenyl)-2-urea derivatives were slightly less active against VEGFR and less selective, being more effective against PDGFR (ca. 10-fold) and c-Src (ca. 500-fold). The 3-(3,5-dimethoxyphenyl)-1,6-naphthyridines were generally more potent than the corresponding pyrido[2,3-d]pyrimidines against both VEGFR and FGFR (2- to 20-fold), with only slightly increased PDGFR and c-Src activity. The 3-(3,5-dimethoxyphenyl)-1,6-naphthyridine 2-ureas were also low nanomolar inhibitors of the growth of human umbilical vein endothelial cells (HUVECs) stimulated by serum, FGF, or VEGF, at concentrations that did not affect the growth of representative tumor cell lines, and were more (3- to 65-fold) potent than the corresponding pyrido[2,3-d]pyrimidines.
Nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 9. Formal synthesis of (-)-pinidine and total synthesis of (-)-histrionicotoxin, (+)-histrionicotoxin and (-)-histrionicotoxin 235A
Davison, Edwin C.,Fox, Martin E.,Holmes, Andrew B.,Roughley, Stephen D.,Smith, Catherine J.,Williams, Geoffrey M.,Davies, John E.,Raithby, Paul R.,Adams, Joseph P.,Forbes, Ian T.,Press, Neil J.,Thompson, Mervyn J.
, p. 1494 - 1514 (2007/10/03)
An intramolecular hydroxylamine-alkyne cyclisation is used for the enantioselective synthesis of the cyclic nitrones 36 and 44. We have demonstrated the use of a novel nitrone protection strategy by cycloaddition of styrene to the cyclic nitrone 44 in the synthesis of the spirocyclic core of the histrionicotoxin family of alkaloids. Deprotection by dipolar cycloreversion of the styrene adduct (the bicyclic isoxazolidine 39) and in situ intramolecular dipolar cycloaddition of a pendant (Z)-α,β-unsaturated nitrile to the intermediate nitrone 50 gave the isoxazolidine 51 in high yield with a surprising degree of regioselectivity compared with the corresponding (Z)-enyne 36. The method is amenable to the synthesis of both enantiomers 51 and 62 of the tricyclic core structure which can be converted by way of the common intermediates (e.g. 53 and ent-53) respectively into the natural configuration of alkaloids (-)-histrionicotoxin 1 and (-)-histrionicotoxin 235A 65 as well as the unnatural (+)-histrionicotoxin 63.
Synthesis of extremely simplified compounds possessing the key pharmacophore units of taxol, phenylisoserine and oxetane moieties
Fuji, Kaoru,Watanabe, Yukari,Ohtsubo, Tadamune,Nuruzzaman, Mohammad,Hamajima, Yoshio,Kohno, Michiaki
, p. 1334 - 1337 (2007/10/03)
Straight chain compounds having a phenylisoserine unit and an oxetane ring at the α- and ω- position, respectively as extremely simplified analogues of taxol were prepared. None of these compounds showed promising tubulin inhibitory activity.
Synthesis of the Cyclophane Tetramethoxyturriane: a Derivative of the Phenolic Cyclophanes of Grevillea striata R. Br.
Sargent, Melvyn V.,Wangchareontrakul, Sirichai
, p. 129 - 132 (2007/10/02)
The synthesis of 9,10,11,12,13,14,15,16,17,18,19,20,21,22-tetradecahydro-2,4,6,24-tetramethoxy-5,8-ethenobenzocycloeicosene (tetramethoxyturriane) (9) a derivative of the phenolic cyclophanes extracted from the wood of Grevillea striata R.Br., is reported.The key steps in this synthesis were the construction of the biphenyl linkage of the molecule using dihydro-oxazole chemistry and the closure of the macrocycle by oxidative coupling of a diacetylene.
