81885-74-7Relevant academic research and scientific papers
Chemoselective reduction of α,β-unsaturated carbonyl compounds in the presence of CuPd alloy nanoparticles decorated on mesoporous graphitic carbon nitride as highly efficient catalyst
Bayrak, Cetin,Menzek, Abdullah,Sevim, Melike
, (2021/12/09)
Herein, we reported reductions of acid, amide, ester and ketone groups with selectivity (>99%) by the catalytic transfer hydrogenation of with CuPd alloy nanoparticles (NPs) decorated on mesoporous graphitic carbon nitride (Cu50Pd50/mpg-C3N4) catalyst under mild conditions in a water/methanol mixture. CuPd alloy NPs were synthesized by the co-reduction of palladium (II) acetylacetonate and copper(II) acetylacetonate in oleylamine (OAm) solution by the reduction of morpholine-borane solution and then assembled on mpg-C3N4 via liquid phase self‐assembly method. The α, β-unsaturated carbonyl compounds were obtained from the condensation reaction of the benzaldehyde derivatives with acetone derivatives. Cu50Pd50/mpg-C3N4 nanocatalyst was characterized by TEM, XRD, XPS, BET and ICP‐MS. Cu50Pd50/mpg-C3N4 nanocatalyst is highly active catalyst for the reduction of various organic groups and converted to high yield and 99% selectivity. The superior Cu50Pd50/mpg-C3N4 nanocatalyst is highly efficient and reusable catalyst which is reuse after 5 cycle with 98% conversion.
Chemoselective and metal-free reduction of α,β-unsaturated ketones by: In situ produced benzeneselenol from O -(tert -butyl) Se-phenyl selenocarbonate
Ballarotto, Marco,Siciliano, Carlo,Temperini, Andrea
, p. 33706 - 33717 (2020/10/22)
The carbon-carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use of toxic Se/CO mixture and NaSeH, or the smelly and air-sensitive benzeneselenol, is avoided. This journal is
Synthesis of functionalized alkyl substituted benzoquinones by Rh-catalyzed additions of boronic acids
Veguillas, Marcos,Rojas-Martín, Jaime,Ribagorda, María,Carre?o, M. Carmen
supporting information, p. 5386 - 5394 (2017/07/10)
A general synthetic route to γ-oxo alkyl or α-hydroxy benzyl 2-substituted benzoquinones has been developed through a one-pot Rh-catalyzed C-C bond formation/oxidative demethylation sequence from 2,5-dimethoxy aryl boronic acids and several electron deficient alkenes or aldehydes. The process allows rapid access to functionalized benzoquinones under very mild conditions and good yields. We disclose the first example of a Rh-catalyzed 1,4-addition reaction of benzoquinonyl boronic acid to methyl vinyl ketone and other conjugate acceptors, which allows the direct synthesis of 2-(γ-functionalized alkyl) substituted benzoquinones.
Novel diarylheptanoids as inhibitors of TNF-α production
Dhuru, Sameer,Bhedi, Dilip,Gophane, Dnyaneshwar,Hirbhagat, Kiran,Nadar, Vijaya,More, Dattatray,Parikh, Sapna,Dalal, Roda,Fonseca, Lyle C.,Kharas, Firuza,Vadnal, Prashant Y.,Vishwakarma, Ram A.,Sivaramakrishnan
supporting information; experimental part, p. 3784 - 3787 (2011/07/31)
Synthesis and anti-inflammatory activity of novel diarylheptanoids [5-hydroxy-1-phenyl-7-(pyridin-3-yl)-heptan-3-ones and 1-phenyl-7-(pyridin-3-yl) hept-4-en-3-ones] as inhibitors of tumor necrosis factor-α (TNF-α) production is described in the present article. The key reactions involve the formation of a β-hydroxyketone by the reaction of substituted 4-phenyl butan-2-ones with pyridine-3-carboxaldehyde in presence of LDA and the subsequent dehydration of the same to obtain the α,β-unsaturated ketones. Compounds 4i, 5b, 5d, and 5g significantly inhibit lipopolysaccharide (LPS)-induced TNF-α production from human peripheral blood mononuclear cells in a dose-dependent manner. Of note, the in vitro TNF-α inhibition potential of 5b and 5d is comparable to that of curcumin (a naturally occurring diarylheptanoid). Most importantly, oral administration of 4i, 5b, 5d, and 5g (each at 100 mg/kg) but not curcumin (at 100 mg/kg) significantly inhibits LPS-induced TNF-α production in BALB/c mice. Collectively, our findings indicate that these compounds may have potential therapeutic implications for TNF-α-mediated auto-immune/inflammatory disorders.
2,4-Diaminothienopyrimidine Analogues of Trimetrexate and Piritrexim as Potential Inhibitors of Pneumocystis Carinii and Toxoplasma gondii Dihydrofolate Reductase
Rosowsky, Andre,Mota, Clara E.,Wright, Joel E.,Freisheim, James H.,Heusner, James J.,et al.
, p. 3103 - 3112 (2007/10/02)
A series of eight previously undescribed 2,4-diaminothienopyrimidine analogues of the potent dihydrofolate reductase (DHFR) inhibitors trimetrexate (TMQ) and piritrexim (PTX) were synthesized as potential drugs against Pneumocystis carinii and Toxoplasma gondii, which are major causes of severe opportunistic infections in AIDS patients. 2,4-Diamino-5-methyl-6-(aryl/aralkyl)thienopyrimidines with 3,4,5-trimethoxy or 2,5-dimethoxy substitution in the aryl/aralkyl moiety and 2,4-diamino-5-(aryl/aralkyl)thienopyrimidines with 2,5-dimethoxy substitution in the aryl/aralkyl moiety were obtained by reaction of the corresponding 2-amino-3-cyanothiophenes with chloroformamidine hydrochloride.The aryl group in the 5,6-disubstituted analogues was either attached directly to the hetero ring or was separated from it by one or two carbons, whereas the aryl group in the 5-monosubstituted analogues was separated from the hetero ring by two or three carbons. 2-Amino-3-cyano-5-methyl-6-(aryl/alkyl)thiophene intermediates for the preparation of the 5,6-disubstituted analogues were prepared from ω-aryl-2-alkylidenemalononitriles and sulfur in the presence of a secondary amine, and 2-amino-3-cyano-4-(aryl/aralkyl)thiophene intermediates for the preparation of the 5-monosubstituted analogues were obtained from ω-aryl-1-chloro-2-alkylidenemalononitriles and sodium hydrosulfide.Synthetic routes to the heterofore unknown ylidenemalononitriles, and the ketone precursors thereof, were developed.The final products were tested in vitro as inhibitors of DHFR from Pneumocystis carinii, Toxoplasma gondii, rat liver, beef liver, and Lactobacillus casei.A select number of previously known 2,4-diaminothienopyrimidines lacking the 3,4,5-trimethoxyphenyl and 2,5-dimethoxyphenyl substitution pattern of TMQ and PTX, respectively, were also tested for comparison.None of the compounds was as potent as TMQ or PTX, and while some of them showed some selectivity in their binding to Pneumocystis carinii and Toxoplasma gondii versus rat liver DHFR, this effect was not deemed large enough to warrant further preclinical evaluation.
