153035-39-3Relevant academic research and scientific papers
Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization-Hydroboration of Unactivated Alkenes
Cooper, Phillippa,Engle, Keary M.,Jankins, Tanner C.,Martin, Ruben,Martin-Montero, Raul
supporting information, p. 14981 - 14986 (2021/09/29)
A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp3)-H bonds aided by native directing groups is described herein. The method is characterized by its simplicity, exquisite regio- and chemoselectivity, and wide substrate scope, offering a complementary site-selectivity pattern to other metal-catalyzed borylation reactions and chain-walking protocols.
α,?-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA
Chattopadhyay, Shital K.,Ghosh, Subhankar,Sarkar, Sarita,Bhadra, Kakali
supporting information, p. 2524 - 2533 (2019/12/11)
An alternate synthetic route to the important anticancer drug suberoylanilide hydroxamic acid (SAHA) from its α,?-didehydro derivative is described. The didehydro derivative is obtained through a cross metathesis reaction between a suitable terminal alkene and N-benzyloxyacrylamide. Some of the didehydro derivatives of SAHA were preliminarily evaluated for anticancer activity towards HeLa cells. The administration of the analogues caused a significant decrease in the proliferation of HeLa cells. Furthermore, one of the analogues showed a maximum cytotoxicity with a minimum GI50 value of 2.5 μg/mL and the generation of reactive oxygen species (ROS) as some apoptotic features.
Anti-Markovnikov Hydroazidation of Alkenes by Visible-Light Photoredox Catalysis
Wang, Juan-Juan,Yu, Wei
supporting information, p. 3510 - 3514 (2019/02/19)
The anti-Markovnikov hydroazidation of alkenes has been accomplished under visible-light irradiation by using [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as the photocatalyst and trimethylsilyl azide as the azidating agent. The reactions were greatly facilitated by water, the beneficial effect of which can be attributed to its participation in the reaction as the hydrogen donor, as indicated by deuterium isotope experiments. The reactions proceed under solvent free conditions in the presence of water. 4-Dimethylaminopyridine also exhibited a beneficial effect on the reactions. The present method enabled hydroazidation of several types of unactivated alkenes with good yields and high regioselectivity.
Design and synthesis of novel isoxazole-based HDAC inhibitors
Conti, Paola,Tamborini, Lucia,Pinto, Andrea,Sola, Laura,Ettari, Roberta,Mercurio, Ciro,De Micheli, Carlo
experimental part, p. 4331 - 4338 (2010/09/16)
A series of isoxazole-based histone deacetylase (HDAC) inhibitors structurally related to SAHA were designed and synthesized. The isoxazole moiety was inserted in the vicinity of the Zn2+-binding group in order to check its participation in the coordinating process. New isoxazole-based histone deacetylase inhibitors structurally related to SAHA were designed and synthesized to check the participation of the isoxazole moiety in the Zn 2+coordination.
Effect of substitution on the intramolecular 1,3-dipolar cycloaddition of alkene tethered muenchnones
Belanger, Guillaume,April, Myriam,Dauphin, Etienne,Roy, Stephanie
, p. 1104 - 1111 (2007/10/03)
(Chemical Equation Presented) A sequence of chemoselective activation of N-acylaminoacids, muenchnone generation, intramolecular 1,3-dipolar cycloaddition, and ring opening efficiently generated functionalized polycyclic structures such as cyclopenta[b]py
Radical Translocation Reactions across Amides. 1,5-Hydrogen-Transfer Reactions of o-Iodobenzamides and N-(o-Iodobenzyl) Amides
Curran, Dennis P.,Liu, Hohgtao
, p. 1377 - 1394 (2007/10/02)
Radicals derived from N,N-disubstituted o-iodobenzamides undergo rapid 1,5-hydrogen-transfer reactions.The regioselectivity of these reactions is coupled to the rotamer population of the starting iodobenzamide, and the products vary with changing amide substituents.Related 1,5-hydrogen-transfer reactions are observed for N-alkyl-N-(o-iodobenzyl)-benzamides and -acetamides.
Charge-directed conjugate addition reactions of silylated α-β- unsaturated amidate anions
Cooke Jr.,Pollock
, p. 7474 - 7481 (2007/10/02)
A variety of N-substituted α-silylated-α,β-unsaturated amidate anions (2) have been found to be excellent Michael acceptors in charge-directed conjugate addition reactions with Grignard and organolithium reagents. The effects of olefin substitution, Si-substitution, N-substitution, and amidate counterion have been studied. Anionic acceptors may be prepared in situ by the addition of silylated vinyllithium reagents to isocyanates and then allowed to undergo conjugate addition reactions with subsequently added nucleophiles, but it was found to be more efficient to isolate neutral acceptors and regenerate the acceptor anion through the use of excess nucleophile. β-Substituted acceptors were found to react only with reactive organolithium reagents while a β,β-disubstituted acceptor failed to undergo conjugate addition reactions. A primary amide acceptor (14d) also undergoes addition reactions with larger quantitites of nucleophiles suggesting that dianionic amidate acceptors (31) are involved. Diene acceptor 24 was found to undergo a 1,6-addition reaction with n-BuLi. Sodium and potassium amidate salts were found to be inferior to lithium and magnesium salts in addition reactions in keeping with the expectation that an increase in carbonyl-group charge burden retards conjugate reactions. Triphenylsilyl-containing acceptor 16 was found to be more reactive in reactions with n-BuMgCl but less reactive with bulkier tert-BuMgCl. Adduct dianions can be monoalkylated with alkyl iodides and used in Peterson olefination reactions.
