32776-14-0Relevant academic research and scientific papers
In vivo potent BM635 analogue with improved drug-like properties
Poce, Giovanna,Cocozza, Martina,Alfonso, Salvatore,Consalvi, Sara,Venditti, Giulia,Fernandez-Menendez, Raquel,Bates, Robert H.,Barros Aguirre, David,Ballell, Lluis,De Logu, Alessandro,Vistoli, Giulio,Biava, Mariangela
supporting information, p. 539 - 550 (2018/01/17)
BM635 is the hit compound of a promising anti-TB compound class. Herein we report systematic variations around the central pyrrole core of BM635 and we describe the design, synthesis, biological evaluation, pharmacokinetic analysis, as well as in vivo TB mouse efficacy studies of novel BM635 analogues that show improved physicochemical properties. This hit-to-lead campaign led to the identification of a new analogue, 4-((1-isopropyl-5-(4-isopropylphenyl)-2-methyl-1H-pyrrol-3-yl)methyl)morpholine (17), that shows excellent activity (MIC = 0.15 μM; SI = 133) against drug-sensitive Mycobacterium tuberculosis strains, as well as efficacy in a murine model of TB infection.
NOVEL PROCESS FOR PREPARING SYNTHESIS INTERMEDIATES USING PRODUCTS OF NATURAL ORIGIN AND USE OF THE INTERMEDIATES OBTAINED
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Paragraph 0231, (2017/12/15)
Disclosed is a process for preparing a product of formula I: wherein the reaction is catalyzed both by thiamine or a thiamine salt and by ascorbic acid in a form which is free or salified or an organic acid salt of an alkaline metal, preferably sodium acetate, potassium tartrate, sodium succinate, or a reductone, preferably 2-hydroxypropanedial or 2,3-dihydroxycyclopent-2-ene-1-one in an organic solvent.
Regioselective cobalt-catalysed hydrovinylation for the synthesis of non-conjugated enones and 1,4-diketones
Kersten, Laura,Hilt, Gerhard
, p. 863 - 869 (2012/05/04)
The highly regioselective cobalt-catalysed 1,4-hydrovinylation of terminal alkenes with 2-trimethylsilyloxy-1,3-butadiene generates in a stereospecific fashion unsaturated E-configured silyl enol ether intermediates that are suitable for diastereoselective Mukaiyama-aldol reactions with bulky aliphatic aldehydes. The acidic hydrolysis of the enol ethers to γ,δ- unsaturated ketones followed by ozonolysis can be used for the synthesis of various 1,4-diketones and polycarbonyl derivatives. The 1,4-diketones and polycarbonyl derivatives were successfully tested for the synthesis of some mono- and bis-pyrrole derivatives. The γ,δ-unsaturated ketones are useful building blocks (e.g., in natural product synthesis) and can be generated in a one-pot procedure. Copyright
Ruthenium-catalyzed three-component coupling via hydrative conjugate addition of alkynes to alkenes: One-pot synthesis of 1,4-dicarbonyl compounds
Chen, Yiyun,Park, Sung Hwan,Lee, Chung Whan,Lee, Chulbom
supporting information; experimental part, p. 2000 - 2004 (2011/11/07)
A catalytic three-way rendezvous: Terminal alkynes undergo metal vinylidene formation, anti-Markovnikov hydration to give a metal acyl complex, and conjugate addition to produce synthetically useful 1,4-dicarbonyl compounds under ruthenium catalysis. This one-pot three-component coupling reaction is a useful platform for further exploration in alkyne functionalization.
Gold(III) complexes catalyze deoximations/transoximations at neutral pH
Isart, Carles,Bastida, David,Bures, Jordi,Vilarrasa, Jaume
experimental part, p. 3275 - 3279 (2011/05/12)
Golden solution: A neutral solution of AuBr3, containing [AuBr2(OH)2]- in equilibrium with [AuBr 3(OH)]- and [AuBr4]-, promotes the chemoselective hydrolysis of robust oximes into carbonyl compounds without racemization (see scheme). The food additive diacetyl acts as a NH 2OH-trapping agent, thus avoiding the formation of gold nanoparticles and allows the reaction to run catalytically. Copyright
Rauhut-Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes
Shanbhag, Pramod,Nareddy, Pradeep R.,Dadwal, Mamta,Mobin, Shaikh M.,Namboothiri, Irishi N. N.
supporting information; experimental part, p. 4867 - 4873 (2010/11/17)
Reaction of nitroalkenes or nitrodienes with methyl vinyl ketone (MVK) or acrylate in the presence of the imidazole-LiCl catalyst system provides Rauhut-Currier (vinylogous Morita-Baylis-Hillman) adducts in moderate yield. Under similar conditions (imidaz
Pd(0)-Catalyzed Conjugate Addition of Benzylzinc Chlorides to α,β-Enones in An Atmosphere of Carbon Monoxide: Preparation of 1,4-Diketones
Yuguchi, Motoki,Tokuda, Masao,Orito, Kazuhiko
, p. 908 - 914 (2007/10/03)
Pd(0)-catalyzed conjugate addition of benzylzine chloride to methyl vinyl ketone in the presence of chlorotrimethylsilane and lithium chloride in an atmosphere of carbon monoxide at room temperature afforded 1-phenyl-2,5-hexanedione monosilyl enol ether. In this catalytic carbonylation, four components are connected in one reaction. Successive acidic workup generated a variety of 1,4-diketones from substituted benzylzine chlorides or related compounds and α,β-enones. Some products were converted to cyclopentenones or five-membered heterocyclic compounds containing an N, O, or S atom.
A convenient synthesis of 1,4-diketones
Motoyoshiya,Hongo,Tanaka,Hayashi
, p. 997 - 1000 (2007/10/02)
A simple and short synthesis of 1,4-diketones was achieved via 2-chloro-5-methylthio-2,5-hexadienes and their hydrolysis with titanium tetrachloride.
