61444-26-6Relevant academic research and scientific papers
Photoinduced Olefin Diamination with Alkylamines
Angelini, Lucrezia,Govaerts, Sebastian,Hampton, Charlotte,Leonori, Daniele,Malet-Sanz, Laia,Ruffoni, Alessandro
supporting information, p. 15021 - 15028 (2020/06/17)
Vicinal diamines are ubiquitous materials in organic and medicinal chemistry. The direct coupling of olefins and amines would be an ideal approach to construct these motifs. However, alkene diamination remains a long-standing challenge in organic synthesis, especially when using two different amine components. We report a general strategy for the direct and selective assembly of vicinal 1,2-diamines using readily available olefin and amine building blocks. This mild and straightforward approach involves in situ formation and photoinduced activation of N-chloroamines to give aminium radicals that enable efficient alkene aminochlorination. Owing to the ambiphilic nature of the β-chloroamines produced, conversion into tetra-alkyl aziridinium ions was possible, thus enabling diamination by regioselective ring-opening with primary or secondary amines. This strategy streamlines the preparation of vicinal diamines from multistep sequences to a single chemical transformation.
Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method
Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Piltan, Mohammad Amin
, p. 113 - 124 (2019/07/30)
Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].
Oxo-rhenium-catalyzed deoxydehydration of polyols with hydroaromatic reductants
Boucher-Jacobs, Camille,Nicholas, Kenneth M.
supporting information, p. 1985 - 1990 (2015/06/08)
Several dihydroaromatic compounds are shown to be effective reducing agents in the oxo-metal-catalyzed deoxydehydration of diols and polyols to produce olefins and the corresponding arenes. NH4ReO4 and MeReO3 are active catalysts for the reactions. The most effective of the hydroaromatic reductants is indoline, which is oxidized to indole. Yields for a variety of diols and polyols range from 35% to 99%. Two hydrogen donors, 1,3-cyclohexadiene and dihydroanthracene, engage in tandem DODH/cycloaddition reactions. Competition experiments show that indoline is more reactive than representative alcohols in H-transfer. Indoline is shown to reduce MeReO3 to MeReO2 via an isolable adduct, MeReO3(indoline) (4), which has been structurally characterized and is suggested to be an intermediate in the catalytic DODH process.
Caffeine-based gold(I) N-heterocyclic carbenes as possible anticancer agents: Synthesis and biological properties
Bertrand, Benoiit,Stefan, Loic,Pirrotta, Marc,Monchaud, David,Bodio, Ewen,Richard, Philippe,Le Gendre, Pierre,Warmerdam, Elena,De Jager, Marina H.,Groothuis, Geny M.M.,Picquet, Michel,Casini, Angela
supporting information, p. 2296 - 2303 (2014/03/21)
A new series of gold(I) N-heterocyclic carbene (NHC) complexes based on xanthine ligands have been synthesized and characterized by mass spectrometry, NMR, and X-ray diffraction. The compounds have been tested for their antiproliferative properties in human cancer cells and nontumorigenic cells in vitro, as well as for their toxicity in healthy tissues ex vivo. The bis-carbene complex [Au(caffein-2-ylidene)2][BF4] (complex 4) appeared to be selective for human ovarian cancer cell lines and poorly toxic in healthy organs. To gain preliminary insights into their actual mechanism of action, two biologically relevant in cellulo targets were studied, namely, DNA (more precisely a higher-order DNA structure termed G-quadruplex DNA that plays key roles in oncogenetic regulation) and a pivotal enzyme of the DNA damage response (DDR) machinery (poly-(adenosine diphosphate (ADP)-ribose) polymerase 1 (PARP-1), strongly involved in the cancer resistance mechanism). Our results indicate that complex 4 acts as an efficient and selective G-quadruplex ligand while being a modest PARP-1 inhibitor (i.e., poor DDR impairing agent) and thus provide preliminary insights into the molecular mechanism that underlies its antiproliferative behavior.
Design, synthesis, antiviral, and cytostatic evaluation of novel isoxazolidine analogs of homonucleotides
Lysakowska, Magdalena,Balzarini, Jan,Piotrowska, Dorota G.
, p. 341 - 353 (2014/05/20)
Moderate diastereoselectivities (d.e. 2-62%) of isoxazolidine homonucleotides were observed for cycloadditions between N-methyl-C- (diethoxyphosphoryl)nitrone and N-allyl nucleobases, with trans-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil-containing cycloadducts. The cis- and trans-isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33-100 μM.
N 7-Tosyltheophylline (TsTh): A highly efficient reagent for the one-pot synthesis of n 7-alkyltheophyllines from alcohols
Soltani Rad, Mohammad Navid,Behrouz, Somayeh,Najafi, Hosnieh
, p. 1380 - 1388 (2014/06/09)
A convenient and highly efficient one-pot N-alkylation of theophylline from alcohols via N 7-tosyltheophylline (TsTh) is described. In this protocol, the treatment of primary and/or secondary alcohols with a mixture of TsTh and 1,8-diazabicyclo[5.4.0]undec-7-ene in refluxing acetonitrile affords the corresponding N 7-alkyltheophylline in good to excellent yields; the reaction was optimized for solvent and base. This methodology is highly efficient for various structurally diverse primary and secondary alcohols. A plausible mechanism for the one-pot N-alkylation of theophylline with alcohols via TsTh has been suggested. Georg Thieme Verlag Stuttgart New York.
Silica sulfuric acid (SSA) as a highly efficient heterogeneous catalyst for persilylation of purine and pyrimidine nucleobases and other N-heterocycles using HMDS
Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Divar, Masoumeh,Behrouz, Somayeh
experimental part, p. 1943 - 1954 (2010/11/16)
Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts. Copyright
One-pot synthesis of n-alkyl purine, pyrimidine and azole derivatives from alcohols using ph3p/ccl4: A rapid route to carboacyclic nucleoside synthesis
Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Asrari, Zeinab,Behrouz, Marzieh,Aminia, Zohreh
experimental part, p. 3067 - 3076 (2009/12/28)
A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n- butylammonium iodide (TBAI) in refluxing N,N-dimethylformamide, furnishes the corresponding N-alkyl derivatives in good yields. This methodology is highly efficient for various structurally diverse primary alcohols and also useful for N-alkylation of other N-heterocycles containing an acidic N-H bond.
Potentiation of cADPR-induced Ca2+-release by methylxanthine analogues
Cavallaro, Rosaria A.,Filocamo, Luigi,Galuppi, Annamaria,Galione, Antony,Brufani, Mario,Genazzani, Armando A.
, p. 2527 - 2534 (2007/10/03)
Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7- hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR- induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.
