99416-99-6

Usage

Uses

Used in Pharmaceutical Industry:
7-Methoxy-1-naphthaleneethanol is used as a key intermediate in the synthesis of Agomelatine (A430000) and its analogues, which are new melatoninergic ligands. These compounds have potential applications in the treatment of various disorders related to melatonin, such as sleep disorders, mood disorders, and circadian rhythm disturbances.

Upstream product

• 6836-21-1 ethyl 2-(7-methoxynaphthalen-1-yl)acetate 
• 176727-95-0 2-(2-methoxynaphthalen-8-yl)acetaldehyde 
• 3453-55-2 1-(7-methoxy-1-naphthalenyl)ethanone 
• 3453-56-3 1-(7-hydroxy-1-naphthalenyl)ethanone 
• 1523-11-1 naphthalen-2-yl acetate 
• 135-19-3 β-naphthol 
• 99416-97-4 ethyl 1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-1-naphthaleneacetate 
• 4521-28-2 4-(4-Methoxyphenyl)butyric acid 
• 6836-19-7 7-Methoxy-1-tetralone 
• 6836-22-2 2-(7-methoxynaphthalen-1-yl)acetic acid 
• 75-21-8 oxirane 
• 185336-03-2 methyl 2-(7-methoxynaphthalen-1-yl)acetate 

Downstream Products

• 99439-47-1 3-<2-(7-methoxy-1-naphthyl)ethyl>-2-cyclohexeneone 
• 139525-77-2 2-(7-methoxynaphthalen-1-yl)ethanamine hydrochloride 
• 138112-76-2 agomelatine 
• 1441343-98-1 1-[2-(7-methoxynaphthalen-1-yl)ethyl]-3.5.7-triaza-1-azoniatricyclo[3.3.1.1³'⁷]decane 4-nitrobenzene sulfonate 
• 1430225-76-5 2-(7-methoxynaphthalen-1-yl)ethyl 4-nitrobenzene sulfonate 
• 138113-09-4 2-(7-methoxynaphth-1-yl)ethylamine 
• 99417-10-4 7-methoxy-1-naphthylethyl benzenesulfonate 

Relevant academic research and scientific papers

PROCESS FOR THE SYNTHESIS OF AGOMELATINE

Process for the industrial synthesis of the compound of formula (I):

FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS

The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a disease or disorder, such as a proliferative disease (preferably cancer), using compounds of the invention.

Simple and Efficient Process for the Large-Scale Preparation of Agomelatine: An Antidepressant Drug

A simple and efficient process for the large-scale preparation of agomelatine (1), an antidepressant drug is, described. Agomelatine was prepared in a linear manner starting from readily available, inexpensive 2-naphthol. Key steps in the synthesis are Friedel-Crafts acylation of 2-naphthyl acetate with chloroacetyl chloride, reduction of keto intermediate, and nucleophilic displacement of chloro intermediate with sodium diformylamide. A systemic approach was described to streamline the process into a robust scalable process by controlling the impurities.

Total synthesis of agomelatine via Friedel-Crafts acylation followed by Willgerodt-Kindler reaction

Total synthesis of antidepressant drug, agomelatine is reported. Regio selective Friedel-Crafts acylation followed by Willgerodt-Kindler reactions is used as the key steps for the synthesis of agomelatine.

Process for the preparation of agomelatine

Disclosed is a process for the synthesis of Agomelatine (1), N-(2-(7-methoxynaphthalen-1-yl)ethyl)acetamide from ethyl 2-(7-methoxynaphthalen-1-yl)acetate (4). Said synthesis method is particularly advantageous compared with known procedures because it uses low-cost reagents under mild reaction conditions and allows the isolation of a product with excellent yields and quality.

PROCESS FOR THE PREPARATION OF AGOMELATINE

The present invention provides a process for the preparation of agomelatine and its intermediate compounds. The invention also provides an intermediate compound of agomelatine represented by Formula (V).

Novel conformationally constrained analogues of agomelatine as new melatoninergic ligands

Novel conformationally restricted analogues of agomelatine were synthesized and pharmacologically evaluated at MT1 and MT2 melatoninergic receptors. Replacement of the N-Acetyl side chain of agomelatine by oxathiadiazole-2-oxide (compound 3), oxadiazole-5(4H)-one (compound 4), tetrazole (compound 5), oxazolidinone (compound 7a), pyrrolidinone (compound 7b), imidazolidinedione (compound 12), thiazole (compounds 13 and 14) and isoxazole moieties (compound 15) led to a decrease of the melatoninergic binding affinities, particularly at MT1. Compounds 7a and 7b exhibiting nanomolar affinity towards the MT2 receptors subtypes have shown the most interesting pharmacological results of this series with the appearance of a weak MT2-selectivity.

PROCESS FOR THE PREPARATION OF AGOMELATINE

The present invention provides a process for the preparation of agomelatine and its intermediate compounds. The invention also provides an intermediate compound of agomelatine represented by Formula (V).

PROCESS FOR THE PREPARATION OF AGOMELATINE

The present invention provides a process for the preparation of agomelatine and its intermediate compounds. The invention also provides intermediate compounds of agomelatine represented by Formula IV, Formula V and Formula VIII. Formula IV Formula V Formula VIII

Synthesis and structure - Activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands

A previous paper reported the synthesis of melatonin receptor ligands. In order to complete the structure-activity relationships and to obtain antagonists to the melatonin receptor, a new series of naphthalenic analogues of melatonin have been synthesized