22621-56-3

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 112374-18-2 (2S,3S)-2-(3-Methoxy-phenyl)-4-methylene-cyclopentane-1,1,3-tricarboxylic acid dimethyl ester 
• 112374-17-1 (2S,3R)-2-(3-Methoxy-phenyl)-4-methylene-cyclopentane-1,1,3-tricarboxylic acid dimethyl ester 
• 1325732-44-2 4-ethyl 1,1-dimethyl 6-(3-methoxyphenyl)cyclohex-3-ene-1,1,4-tricarboxylate 
• 1325732-43-1 3-ethyl 1,1-dimethyl 6-(3-methoxyphenyl)cyclohex-3-ene-1,1,3-tricarboxylate 
• 476358-95-9 dimethyl 2-(3-methoxyphenyl) malonate 
• 1259433-61-8 C₂₉H₂₉NO₇ 
• 138334-35-7 Acetic acid (3S,4R)-7-chloro-1-(2-dimethylamino-ethyl)-4-(3-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester 
• 138334-96-0 (3R,4S)-7-Chloro-3-hydroxy-4-(3-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 
• 138334-96-0 (3S,4S)-7-Chloro-3-hydroxy-4-(3-methoxy-phenyl)-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 
• 138334-77-7 2-[2-(5-Chloro-2-nitro-phenyl)-1-(3-methoxy-phenyl)-ethyl]-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Synthesis and highly potent anti-inflammatory activity of licofelone- and ketorolac-based 1-arylpyrrolizin-3-ones

Since NSAIDs are commonly used anti-inflammatory agents that produce adverse effects, there have been ongoing efforts to develop more effective and less toxic compounds. Based on the structure of the anti-inflammatory pyrrolizines licofelone and ketorolac

Reductive Knoevenagel Condensation with the Zn-AcOH System

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Intermolecular Reductive Couplings of Arylidene Malonates via Lewis Acid/Photoredox Cooperative Catalysis

A cooperative Lewis acid/photocatalytic reduction of arylidene malonates yields a versatile radical anion species. This intermediate preferentially undergoes intermolecular radical-radical coupling reactions, and not the conjugate addition-dimerization reactivity typically observed in the single-electron reduction of conjugate acceptors. Reported here is the development of this open-shell species in intermolecular radical-radical cross couplings, radical dimerizations, and transfer hydrogenations. This reactivity underscores the enabling modularity of cooperative catalysis and demonstrates the utility of stabilized enoate-derived radical anions in intermolecular bond forming reactions.

Indium(III)-catalyzed knoevenagel condensation of aldehydes and activated methylenes using acetic anhydride as a promoter

The combination of a catalytic amount of InCl3 and acetic anhydride remarkably promotes the Knoevenagel condensation of a variety of aldehydes and activated methylene compounds. This catalytic system accommodates aromatic aldehydes containing a variety of electron-donating and -withdrawing groups, heteroaromatic aldehydes, conjugate aldehydes, and aliphatic aldehydes. Central to successfully driving the condensation series is the formation of a geminal diacetate intermediate, which was generated in situ from an aldehyde and an acid anhydride with the assistance of an indium catalyst.

Selection, synthesis, and anti-inflammatory evaluation of the arylidene malonate derivatives as TLR4 signaling inhibitors

Inhibition of TLR4 signaling is an important therapeutic strategy for intervention in the etiology of several pro-inflammatory diseases. There has been intensive research in recent years aiming to explore this strategy, and identify small molecule inhibitors of the TLR4 pathway. However, the recent failure of a number of advanced drug candidates targeting TLR4 signaling (e.g., TAK242 and Eritoran) prompted us to continue the search for novel chemical scaffolds to inhibit this critical inflammatory response pathway. Here we report the identification of a group of new TLR4 signaling inhibitors through a cell-based screening. A series of arylidene malonate analogs were synthesized and assayed in murine macrophages for their inhibitory activity against LPS-induced nitric oxide (NO) production. The lead compound 1 (NCI126224) was found to suppress LPS-induced production of nuclear factor-kappaB (NF-κB), tumor necrosis factor (TNF-α), interleukin-1β (IL-1β), and nitric oxide (NO) in the nanomolar-low micromolar range. Taken together, this study demonstrates that 1 is a promising potential therapeutic candidate for various inflammatory diseases.

Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: Synthesis of multisubstituted cyclohexenes

From our investigations on phosphine-catalyzed [4+2] annulations between α-alkyl allenoates and activated olefins for the synthesis of cyclohexenes, we discovered a hexamethylphosphorous triamide (HMPT)-catalyzed [4+2] reaction between α-alkyl allenoates