60633-90-1Relevant academic research and scientific papers
Synthesis of Tetrahydroisoquinolines by Visible-Light-Mediated 6- exo -trig Cyclization of α-Aminoalkyl Radicals
Bach, Thorsten,Grübel, Michael,Jandl, Christian
, p. 1825 - 1829 (2019/09/09)
Starting from the respective tertiary α-silylmethyl amines, the intramolecular cyclization of α-aminoalkyl radicals to Michael acceptors produced tetrahydroisoquinolines. The reaction conditions included the use of 5 molpercent of an iridium photoredox catalyst, dimethylformamide as the solvent, and equimolar amounts of water and cesium carbonate as the additives. 13 substrates were synthesized from ortho -alkylbenzaldehydes in a three-step procedure involving a carbonyl condensation, a radical bromination, and a substitution by a secondary α-silylmethyl amine. After optimization of the photocyclization, the reaction delivered tetrahydroisoquinolines in moderate to high yields (41-83percent). A facial diastereoselectivity (dr ? 80:20) was observed with chiral substrates and a crystal structure provided evidence for the relative configuration of the major diastereoisomer. A catalytic cycle with direct electron transfer to the photoexcited metal catalyst is proposed.
Tandem annulation strategy for the convergent synthesis of benzonaphthopyranones: total synthesis of chartarin and O-methylhayumicinone
Ray, Sutapa,Patra, Asit,Mal, Dipakranjan
, p. 3253 - 3267 (2008/09/19)
A Hauser-initiated tandem annulation has been developed for the rapid regiospecific synthesis of benzonaphthopyranones via formation of two rings in one-pot operation. This strategy has been generalized with benzonaphthopyranones 26, 29, 32, and 35. It has also been employed in a short synthesis of chartarin (3) and O-methylhayumicinone (67).
Synthesis and biological properties of novel, uracil-containing histone deacetylase inhibitors
Mai, Antonello,Massa, Silvio,Rotili, Dante,Simeoni, Silvia,Ragno, Rino,Botta, Giorgia,Nebbioso, Angela,Miceli, Marco,Altucci, Lucia,Brosch, Gerald
, p. 6046 - 6056 (2007/10/03)
A novel series of compounds containing a uracil moiety as the connection unit between a phenyl/phenylalkyl portion and a N-hydroxy- polymethylenealkanamide or -methylenecinnamylamide group (uracil-based hydroxamic acids, UBHAs) was tested against maize histone deacetylases (HDACs) and mouse HDAC1. Compounds with a phenyl/benzyl ring at the uracil-C6 position and bearing 4-5 carbon units as well as a m- or p-methylenecinnamyl moiety as a spacer were the most potent inhibitors. In cell-based human HDAC1 and HDAC4 assays, the two UBHAs tested inhibited the HDAC1 but not HDAC4 immunoprecipitate activity. When tested in human leukemia U937 cells, some UBHAs produced G1 phase arrest of the cell cycle. Moreover, 1j showed high antiproliferative and dose-dependent granulocytic differentiation properties. The tested UBHAs displayed weak p21WAF1/CIP1 induction in U937 cells, and 1d and 1j showed high histone H3 and α-tubulin acetylation effects.
Total synthesis of the cytotoxic alkaloid 22-hydroxyacuminatine
Ma, Zhongze,Lee, David Y.W.
, p. 6721 - 6723 (2007/10/03)
The total synthesis of the cytotoxic alkaloid 22-hydroxyacuminatine has been achieved in 14.9% overall yield starting from 2-methylcinnamic acid via the key intermediate 5-ethoxymethylisoquinolin-1-one. The total synthesis of the cytotoxic alkaloid 22-hyd
Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment
-
, (2008/06/13)
Compounds of formula I: as well as pharmaceutically acceptable salts, hydrates and esters thereof, are disclosed. The compounds are useful for treating or preventing prostaglandin mediated diseases. Pharmaceutical compositions containing such compounds and methods of treatment are also included.
Structure-activity relationship on the human EP3 prostanoid receptor by use of solid-support chemistry
Juteau, Helene,Gareau, Yves,Labelle, Marc,Lamontagne, Sonia,Tremblay, Nathalie,Carriere, Marie-Claude,Sawyer, Nicole,Denis, Danielle,Metters, Kathleen M.
, p. 747 - 749 (2007/10/03)
Potent and selective EP3 receptor ligands were found by making a library using solid-support chemistry. These compounds can be obtained by a Suzuki coupling reaction of a solid-supported benzyl bromide using various boronic acids. The yields obtained for this reaction were in the range of 24-95% of arylmethyl cinnamic acid I after cleavage from the Wang resin,
Prostaglandin receptor ligands
-
, (2008/06/13)
Compounds and methods for treating prostaglandin mediated diseases, and certain pharmaceutical compositions thereof are disclosed. The compounds are represented by formula II: Ar1—W—Ar2—X—Q??II The compounds of the invention are structurally different from NSAIDs and opiates, and are antagonists of the pain and inflammatory effects of E-type prostaglandins.
Synthesis of Thiazoloisoindoles by Intramolecualar Cycloaddition-Elimination Reactions of 4-Methyl-5-(substituted)imino-Δ2-1,2,3,4-thiatriazolines
L'abbe, Gerrit,Leurs, Stefan,Sannen, Ingrid,Dehaen, Wim
, p. 4439 - 4446 (2007/10/02)
Fused thiazolidine 11 and thiazoline derivatives 19a-c are obtained by intramolecular cycloaddition-elimination reactions of appropriately substituted 5-iminothiatriazolines 10 and 18a-c.The incorporation of a sidechain phenyl group excercises a favorable effect on cyclization since no reaction is observed with 25.Comparable intermolecular reactions also fail to occur.
Synthesis of Substituted 1,2-Dihydroisoquinolines by the Intramolecular 1,3-Dipolar Alkyl Azide-Olefin Cycloaddition
Liu, Jia-Ming,Young, Jenn-Jong,Li, Yu-Jang,Sha, Chin-Kang
, p. 1120 - 1123 (2007/10/02)
A general synthesis of substituted 1,2-dihydroisoquinolines based on intramolecular 1,3-dipolar cycloaddition of alkyl azides and olefins is described.Reaction of bromide 4 with sodium azide afforded azide 5, which underwent 1,3-dipolar cycloaddition intramolecularly to give triazoline 6 .Rearrangement of triazoline 6 on silica gel gave diazo compound 7.Treatment of 7 with rhodium acetate afforded substituted 1,2-dihydroisoquinoline 9 in good overall yield.
