5665-25-8

Upstream product

• 5060-82-2 7-methoxy-2-naphthol 
• 135653-94-0 7-methoxy-2-trifluoromethanesulfonyloxynaphthalene 
• 5665-24-7 α-Carboxy-β-(7-methoxy-2-naphthyl)-propionsaeure 
• 103143-23-3 2-(bromomethyl)-7-methoxynaphthalene 
• 5665-20-3 20(hydroxymethyl)-7-methoxynaphthalene 

Downstream Products

• 72907-96-1 2-ethoxalyl-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72907-97-2 2-(carbethoxymethyl)-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72907-99-4 2-(carbethoxymethyl)-8-hydroxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72908-00-0 2-(carbamylmethyl)-8-hydroxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72908-01-1 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene 
• 3451-02-3 benzene-1,2,3,4-tetracarboxylic acid tetramethyl ester 
• 5670-11-1 8-methoxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 

Relevant academic research and scientific papers

Synthesis and biological evaluation of new naphtho- and quinolinocyclopentane derivatives as potent melatoninergic (MT1/MT2) and serotoninergic (5-HT2C) dual ligands

We recently reported a series of naphthofuranic compounds as constrained agomelatine analogues. Herein, in order to explore alternative ethyl amide side chain rigidification, naphthocyclopentane and quinolinocyclopentane derivatives with various acetamide modulations were synthesized and evaluated at both melatonin (MT1, MT2) and serotonin (5-HT2C) receptors. These modifications has led to compounds with promising dual affinity and high MTs receptors agonist activity. Enantiomeric separation was then performed on selected compounds allowing us to identify levogyre enantiomers (?)-17g and (?)-17k as the highest (MT1, MT2)/5-HT2C dual ligands described nowadays.

New cyclopenta[a]naphthalene derivatives: Synthesis of 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene as a possible deoxyribonucleic acid binding agent

8-Methoxy-1-oxo-2,3-dihydro-1H-cyclopental[a]naphthalene (4) was converted to the oxalyl derivative (7) by treatment with diethyl oxalate in the presence of sodium ethoxide. Compound 7 in the form of the sodium salt was alkylated with ethyl bromoacetate in DMF to 2-(carbethoxymethyl)-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopenta[a]naphthalene (8). Treatment of 8 with methanolic ammonia yielded the corresponding amide (9). Dealkylation of 8 with 48% HBr and subsequent esterification gave compound 10. Ammonolysis of 10 led to the amide 11, which after reduction and subsequent dehydration of the reduced product afforded the desired compound, 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene (2). Compound 2 was found to be mildly growth inhibitory to L1210 and CCRF-CEM leukemic cells in culture. From thermal transition temperature studies, compound 2 was found to bind to calf thymus DNA and the poly(deoxyribonucleotides), e.g., poly(dG)-poly(dC), poly(dG-dC), poly(dA)-poly(dT), and poly (dA-dT).