22073-92-3

Upstream product

• 33863-57-9 2-(3',4'-dimethoxybenzoylmethyl)benzoic acid 
• 89-51-0 Homophthalic acid 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 1005161-85-2 methyl 2-[(3,4-dimethoxyphenyl)ethynyl]benzoate 
• 37673-11-3 2-(3,4-dimethoxyphenyl)-2-(morpholin-1-yl)acetonitrile 
• 2417-73-4 methyl 2-bromomethylbenzoate 
• 93878-81-0 methyl 2-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)benzoate 
• 2859-78-1 4-Bromoveratrole 
• 6967-45-9 3,4-dimethoxy-N,N-dimethylbenzamide 
• 2728-04-3 N,N-diethyl-ortho-toluamide 

Downstream Products

• 33863-57-9 2-(3',4'-dimethoxybenzoylmethyl)benzoic acid 
• 70555-95-2 3-(3,4-dimethoxyphenyl)-3,4-dihydro-1H-isochromen-1-one 
• 93878-81-0 methyl 2-(2-(3,4-dimethoxyphenyl)-2-oxoethyl)benzoate 
• 1206113-96-3 C₁₇H₁₆N₂O₃ 
• 1396397-40-2 C₁₈H₁₈N₂O₃ 

Relevant academic research and scientific papers

Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin

In this work, a regioselective synthesis of isocoumarins from 2-alkynylbenzoic acid is reported. The transformations proceed smoothly with good yields in water via a metal-free radical pathway. When catalytic TBAB is employed, the reaction provides various isocoumarin derivatives according to the structures of the corresponding precursors. It is believed that TBAB serves as a phase transfer catalyst and radical initiator in the reaction. Compared to previous methodologies, the synthetic procedure reported herein provides a more environmentally benign route for the synthesis of isocoumarins.

Synthesis of 3-arylisocoumarins by using acyl anion chemistry and synthesis of thunberginol A and cajanolactone A

A new strategy for the synthesis of 3-arylisocoumarins and 8-hydroxy-3-arylisocoumarins was investigated by using acyl anion chemistry for the initial C-C bond formation. The obtained keto esters and keto lactones as intermediates underwent based-promoted intramolecular cyclization to afford 3-arylisocoumarins in good yields. The developed methodology was applied for the synthesis of the important natural products thunberginol A and cajanolactone A.

Design, synthesis, and pharmacological evaluation of N-acylhydrazones and novel conformationally constrained compounds as selective and potent orally active phosphodiesterase-4 inhibitors

Among a small series of tested N-acylhydrazones (NAHs), the compound 8a was selected as a selective submicromolar phosphodiesterase-4 (PDE4) inhibitor associated with anti-TNF-α properties measured both in vitro and in vivo. The recognition pattern of compound 8a was elucidated through molecular modeling studies based on the knowledge of the 3D-structure of zardaverine, a PDE4 inhibitor resembling the structure of 8a, cocrystallized with the PDE4. Based on further conformational analysis dealing with N-methyl-NAHs, a quinazoline derivative (19) was designed as a conformationally constrained NAH analogue and showed similar in vitro pharmacological profile, compared with 8a. In addition 19 was found active when tested orally in LPS-evoked airway hyperreactivity and fully confirmed the working hypothesis supporting this work.

Synthesis of 3-substituted isocoumarins and their inhibitory effects on degranulation of RBL-2H3 cells induced by antigen

Eleven 3-substituted isocoumarins and a benzylidenephthalide were synthesized through thermal cyclization reaction of δ- and γ-ketoamides, respectively. Subsequent deprotection of the hydroxyl groups of the resulting isocoumarin and benzylidenephthalide compounds afforded thunberginols A, B, and F., respectively, which originated from the processed leaves of Hydrangea macrophylla Seringe var. thunbergii MAKINO. The synthesized isocoumarins and thunberginols were evaluated for their anti-allergic activity, in which thunberginol B exhibited the highest inhibitory potency on the degranulation of RBL-2H3 cells induced by antigen. Structure - activity relationship studies were carried out to determine the necessary substituents on the 3-phenylisocoumarin skeleton for inhibitory activity.

6-endo-dig Cyclization of heteroarylesters to alkynes promoted by Lewis acid catalyst in the presence of Br?nsted acid

We report a regiocontrolled 6-endo-dig cyclization of 2-(2-arylethynyl)heteroaryl esters occurred under Br?nsted acidic conditions and in the presence of a catalytic amount of Lewis acids such as Cu(OTf)2, AuCl3, or (CF3CO

Synthesis of 3-aryl- and 3-aryl-3,4-dihydroisocoumarins

The condensation of homophthalic acid 6 with the appropriate acid chlorides 7a-c yield the respective isocoumarins 8a-c, which are converted to keto-acids 9a-c by alkaline hydrolysis. The 3,4-dihydroisocoumarins 12a-c are obtained by reduction of the keto

Synthesis of 8-desoxythunberginol A and (±)-8-desoxy-3,4- dihydrothunberginol A

A two step synthesis of title isocoumarin isolated from Homalium longifolium and its conversion into corresponding 3,4-dihydroisocoumarin has been described. 3,4-Dimethoxybenzoyl chloride on condensation with homophthalic acid afforded 3-(3′,4′-dimethoxyphenyl)isocoumarin which was demethylated to furnish the 8-desoxythunberginol A, whereas its sequential saponification, reduction and demethylation yielded the (±)-8-desoxy-3,4- dihydrothunberginol A. The synthesized compounds were examined in vitro for antibacterial activity.

Synthesis of 3-substituted isocoumarins and related natural products

Several N,N-diethyl-2-acylmethylbenzamides (6) were prepared from N,N- diethyl-2-toluamides (4), and the ketoamides (6) were easily cyclized to the corresponding 3-substituted isocoumarins (8) by heating in acetic acid or xylene. This simple procedure was