89951-61-1Relevant articles and documents
Efficient preparation method of 4-hydroxybenzoic esters – Oxidation of substituted Hagemman's ester
Kang, Sein,Kim, Dahye,In, Ik Joon,Koo, Sangho
, p. 2264 - 2266 (2017)
A practical two-step synthetic method of diversely R-substituted 4-hydroxybenzoic esters, which may have wide applications in household chemicals and polymeric materials, was developed by 2:1 coupling between ethyl acetoacetate and aldehydes (RCHO) in t-BuOK/t-BuOH, followed by oxidative aromatization of the resulting Hagemman's esters. Application of the condition using stoichiometric NBS and catalytic TMS·OTf efficiently induced oxidation of the Hagemman's esters to produce 4-hydroxybenzoic esters.
Effect of Aryl-Cyclohexanones and their Derivatives on Macrophage Polarization In Vitro
Biavatti, Maique W.,Dalmarco, Eduardo M.,Lubschinski, Tainá L.,Mohr, Eduarda T. B.,Nardino, Luigi A.,Pollo, Luiz A. E.,Sandjo, Louis P.,da Rosa, Julia S.
, (2022/03/09)
Macrophages are critical in both tissue homeostasis and inflammation, and shifts in their polarization have been indicated as pivotal for the resolution of inflammatory processes. Inflammation is a complex and necessary component of the immune response to stimuli that are harmful to host homeostasis and is regulated by cellular and molecular events that remain a source of ongoing investigation. Among the compounds studied that have potential against autoimmune and inflammatory diseases, cannabinoids are currently highlighted. In this work, nineteen aryl-cyclohexanones diesters and their derivatives were synthesized based on the aryl-cyclohexane skeleton of phytocannabinoids, such as cannabidiol (CBD), and were evaluated for their anti-inflammatory and macrophage polarization potential. The results showed that Compound 4 inhibited the production of nitric oxide in RAW 264.7 macrophages. Furthermore, it reduced the levels of pro-inflammatory cytokines IL-12p70, TNF-α, IFN-γ, MCP-1, and IL-6 while, at the same time, was able to increase the production of anti-inflammatory cytokines IL-4, IL-10, and IL-13. Compound 4 also reduced macrophage apoptosis, increased the expression of the CD206 (mannose receptor) and at the same time, decreased the expression of CD284 (TLR-4 receptor) on the surface of these cells. Finally, it increased the phagocytic capacity and inhibited the phosphorylation of the p65 of NF-kβ. In conclusion,?Compound 4, identified as diethyl-4-hydroxy-2-(4-methoxyphenyl)-4-methyl-6-oxocyclohexane-1–3-dicarboxylate, showed significant anti-inflammatory effect, while demonstrating the ability to transform phenotypically macrophages from the M1 phenotype (pro-inflammatory) to the M2 phenotype (anti-inflammatory). This led us to hypothesize that the main mechanism of anti-inflammatory effect of this molecule is linked to its immune modulation capacity.
Palladium-Catalyzed Tandem γ-Arylation/Aromatization of Cyclohex-2-En-1-One Derivatives: A Route to 3,4-Dihydroanthracen-1(2H)-Ones
Feng, Chen-Guo,Fu, Jian-Guo,Lin, Guo-Qiang,Song, Yi-Kang,Xu, Si-Yu,Zhang, Shu-Sheng
supporting information, p. 3001 - 3005 (2021/05/07)
An intramolecular palladium-catalyzed tandem γ-arylation/aromatization reaction of cyclohex-2-en-1-one derivatives was developed. This work provides a simple and efficient approach for the construction of substituted 3,4-dihydroanthracen-1(2H)-ones in good yields with a broad substrate scope. (Figure presented.).
Sequential one-pot combination of multireactions through multicatalysis: A general approach to rapid assembly of functionalized push-pull olefins, phenols, and 2-methyl-2 H-chromenes
Ramachary, Dhevalapally B.,Ramakumar, Kinthada,Bharanishashank, Adluri,Narayana, Vidadala V.
experimental part, p. 855 - 876 (2011/01/13)
A general, sustainable and practical process for the sequential cascade one-pot synthesis of library of highly substituted push-pull olefins, phenols and 2-methyl-2H-chromenes was reported through multicatalysis cascade (MCC) reactions. Direct sequential
High-yielding synthesis of Nefopam analogues (functionalized benzoxazocines) by sequential one-pot cascade operations
Ramachary, Dhevalapally B.,Narayana, Vidadala V.,Prasad, M. Shiva,Ramakumar, Kinthada
body text, p. 3372 - 3378 (2010/01/06)
An efficient amine-/ruthenium-catalyzed three-step process for the synthesis of Nefopam analogues was achieved through combinations of cascade enamine amination/iso-aromatization/allylation and diene or enyne metathesis as key steps starting from functionalized Hagemann's esters. In this communication, we discovered the application of ruthenium-catalysis on olefins containing free amines without in situ formation of salts.
Organocatalytic cascade reactions based on push-pull dienamine platform: Synthesis of highly substituted anilines
Ramachary, Dhevalapally B.,Ramakumar, Kinthada,Narayana, Vidadala V.
, p. 1458 - 1463 (2007/10/03)
(Chemical Equation Presented) A practical and novel one-pot organocatalytic selective process for the cascade synthesis of highly substituted o-hydroxydiary lamines and o-pyrrolidin-1-yldiarylamines is reported. Direct combination of amine-catalyzed cascade Knoevenagel/Michael/aldol condensation/decarboxylation and cascade enamine amination/isoaromatization of alkyl acetoacetates, aldehydes, and nitrosoarenes furnished the highly functionalized anilines with high yields.
