88692-77-7

Upstream product

• 108-94-1 cyclohexanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 370873-37-3 2-[(4,5-dimethoxyphenyl)(2-naphthylamino)methyl]cyclohexanone 

Downstream Products

• 102020-95-1 2-ethoxy-4-(3,4-dimethoxy-phenyl)-5,6,7,8-tetrahydro-chroman 
• 18977-33-8 2,6-bis(3,4-dimethoxybenzylidene)-cyclohexan-1-one 
• 116897-71-3 2-Amino-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydro-4H-3,1-benzothiazin 

Relevant academic research and scientific papers

Redox-Neutral Cobalt(III)-Catalyzed C-H Activation/Annulation of α,β-Unsaturated Oxime Ether with Alkyne: One-Step Access to Multisubstituted Pyridine

A redox neutral Co(III)-catalyzed annulation of α,β-unsaturated oxime ether with alkyne has been reported. Multisubstituted pyridines were synthesized in good yields without the use of any heavy metal oxidants. The developed methodology tolerates a variety of functional groups. Notably, this transformation has been applied to the late-stage modification of the bioactive molecule dehydropregnenolone.

Asymmetrical meta-methoxylated diarylpentanoids: Rational design, synthesis and anti-cancer evaluation in-vitro

In the present study, a series of forty-five asymmetrical meta-methoxylated diarylpentanoids have been synthesized, characterized and evaluated for their in-vitro anti-cancer potential. Among the forty-five analogs, three compounds (20, 33 and 42) have been identified as lead compounds due to their excellent inhibition against five human cancer cell lines including SW620, A549, EJ28, HT1080 and MCF-7. Structure-activity relationship study on cytotoxicity of tested compounds suggested that the presence of meta-oxygenated phenyl ring played a critical role in enhancing their cytotoxic effects. Compounds 33 and 42 in particular, exhibited strongest cytotoxicity against tested cell lines with the IC50 values ranging from 1.1 to 4.3 μM. Subsequent colony formation assay on SW620 cell line showed that both compounds 33 and 42 possessed strong anti-proliferative activity. In addition, flow cytometry based experiments revealed that these compounds could trigger intracellular ROS production thus inducing G2/M-phase cell arrest and apoptosis. All these results suggested that poly meta-oxygenated diarylpentnoid is a promising scaffold which deserved further modification and investigation in the development of natural product-based anti-cancer drug.

Discovery of new MD2-targeted anti-inflammatory compounds for the treatment of sepsis and acute lung injury

Myeloid differentiation 2 (MD2) is essential to the recognition of lipopolysaccharide (LPS) and the subsequent mediation of toll-like receptor 4 (TLR4)-dependent acute inflammatory disorders including sepsis and acute lung injury. Inhibitors targeting MD2 may provide an alternative means to subdue acute inflammatory diseases. In the present study, 39 bisaryl-1,4-dien-3-one compounds with 5-carbon connection chains were designed and synthesized as MD2 inhibitors based on the analysis of the molecular docking of xanthohumol to MD2. The compound-MD2 interactions were measured by cell-free assays including bis-ANS displacement and SPR, and the active compounds were further tested for MD2 inhibition and anti-inflammatory activities in LPS-challenged macrophages. The most active compound, 1f, was shown to have remarkable protective effects against sepsis shock and pulmonary inflammation. Collectively, we present evidence that bisaryl-1,4-dien-3-one is a new lead structure for the development of anti-inflammatory agents targeting MD2.

Modified calcium oxide as stable solid base catalyst for Aldol condensation reaction

A highly efficient and stable solid-base catalyst for Aldol condensation was prepared by modifying commercial CaO with benzyl bromide in a simple way. It was found that modified CaO can effectively catalyse the Aldol condensation of cyclohexanone and benzaldehyde, as well as various benzaldehydes, to produce 2-benzylidenecyclohexanone with a good selectivity and high yield. Higher yield of 95.8% was obtained over modified CaO after 3 h, which is short compared with the yield of 92.1% after 12 h over commercial CaO. The influence of several reaction parameters, such as temperature, catalyst loading, was investigated. The humidity test over modified CaO reveals that the basic centres of modified CaO are stable for CO2 and moisture. From the results of Fourier transform-infrared (FT-IR) and Thermogravity analysis (TG) characterization, the modifier was bonded on surface of CaO chemically and almost no Ca(OH) 2 formed during the modification process. The type of aldehyde has great influence on the yield of aldol condensation.

Synthesis of 5-aryl-1,2,3,4-tetrahydrobenzo[a]phenanthridines

Previously unknown derivatives of tetrahydro[a]phenanthridine containing annelated benzoquinoline and cyclohexene nuclei were prepared by condensation of azomethines of the 2-naphthylamine series with cyclohexanone. The possibility of synthesis of such compounds without preliminarily preparing Schiff bases was demonstrated. The effect of substituents in the aromatic ring of the azomethine on the yield of the target products was elucidated. The IR, UV, 1H NMR, and mass spectra of the synthesized compounds were discussed.

Synthesis of 2-amino-4-aryl-5,6,7,8-tetrahydro-4H-3,1-benzothiazines

The acid-catalyzed reaction of 2-arylidenecyclohexanones with thiourea afforded 4-aryl-2-imino-1,2,5,6,7,8-hexahydro-4H-3,1-benzothiazine hydrochlorides, which were converted into the corresponding bases.The structure of the 2-amino-4-aryl-5,6,7,8-tetrahy