52644-01-6

Upstream product

• 55218-06-9 1,2,6-trimethoxynaphthalene 
• 43014-31-9 3-(2,3-dimethoxyphenyl)propionyl chloride 
• 10538-48-4 2,3-dimethoxyhydrocinnamic acid 
• 15854-60-1 methyl 3-(2,3-dimethoxyphenyl)propenoate 
• 63307-15-3 4-(2,3-Dimethoxy-phenyl)-1-methanesulfinyl-butan-2-one 
• 7345-82-6 trans-2,3-dimethoxycinnamic acid 
• 66996-59-6 1,6-dibromo-2-methoxynaphthalene 
• 16239-18-2 1,6-dibromo-2-naphthol 
• 52644-00-5 5,6-dimethoxy-1,2-dihydronaphthalene 
• 148728-41-0 1-diazo-4-(2,3-dimethoxyphenyl)-2-butanone 
• 24039-89-2 5,6-dimethoxy-1-tetralone 
• 52643-99-9 1-Hydroxy-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalin 
• 65953-99-3 methyl 3-(2,3-dimethoxyphenyl)propanoate 

Downstream Products

• 39478-90-5 2-(N,N-Dimethylamino)-5,6-dihydroxy-1,2,3,4-tetrahydronaphthalene 
• 470465-23-7 N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide 
• 470465-28-2 C₂₃H₂₃NO₄S 
• 470465-24-8 N-(2-bromo-ethyl)-N-(8,9-dimethoxy-2-methyl-3a,4,5,9b-tetrahydro-3H-cyclopenta[a]naphthalen-4-yl)-benzenesulfonamide 
• 470465-20-4 C₃₀H₃₀O₄ 
• 470465-25-9 N-(2-bromo-ethyl)-N-[4-formyl-5,6-dimethoxy-3-(2-oxo-propyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-benzenesulfonamide 
• 470465-19-1 (4S,5S,3'S)-3'-((Z)-3-Bromo-2-methyl-allyl)-5',6'-dimethoxy-4,5-diphenyl-3',4'-dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene] 
• 470465-31-7 C₂₆H₂₉NO₅Se 
• 57-27-2 MORPHIN 
• 76-57-3 codeine 
• 1027375-99-0 2-Benzylamino-5,6-dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carbonitrile 

Relevant academic research and scientific papers

Synthesis of (-)-morphine

The preparation of the diastereomerically pure β-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1. Copyright

Synthesis and anticholinesterase activity of huperzine a analogues containing phenol and catechol replacements for the pyridone ring

Based upon modeling results obtained using the crystal structure of huperzine A in complex with acetylcholinesterase (AChE), two novel analogues of this potent AChE inhibitor were designed with phenol or catechol rings replacing the pyridone ring. From the modeling studies, the catechol analogue appeared capable of replacing one of the crystallographic waters bridging huperzine with Tyr 130 and Glu 199 of AChE. The synthesis of these materials by use of a palladium catalyzed bicycloannulation strategy is detailed together with the results of AChE inhibition assays.

Synthesis and pharmacological evaluation of 5,6,7,8-tetrahydro-6-amino>-1,2-naphthalenediol: a novel non-selective dopamine-receptor agonist

Based on the hypothesis that simultaneous stimulation of dopamine-D1 and -D2 receptors could be beneficial for the treatment of Parkinson's disease, we prepared 5,6,7,8-tetrahydro-6-amino>-1,2-naphthalenedi

Aminotetralin derivatives

This invention related to new aminotetralin derivatives of formula I STR1 wherein STR2 B is methylene or, when A is --CH2 --CH2 --, --CH=CH--, --NH--CO-- or --CH2 --CO--, B can also be carbonyl or thiocarbonyl; E is a C2 -C4 straight-chain alkylene, optionally substituted by a C1 -C3 alkyl, or is 2-hydroxy-n-propylene, 2-hydroxy-n-butylene or 3-hydroxy-n-butylene; R1 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, nitro, amino, C1 -C3 alkylamino, C1 -C3 dialkylamino, C1 -C3 alkyl, C1 -C3 alkylthio, hydroxy, C1 -C3 alkoxy or phenyl C1 -C3 alkoxy; R2 is hydrogen, chlorine, bromine, hydroxy, C1 -C3 alkoxy phenyl C1 -C3 alkoxy, or C1 -C3 alkyl or, together with R1, can be a C1 -C2 alkylenedioxy; R3 and R4 are each independently selected from hydrogen, fluorine, chlorine, bromine, C1 -C3 alkyl, hydroxy, C1 -C3 alkoxy, nitro, amino, C1 -C3 alkylamino, or C1 -C3 dialkylamino, or together can be methylenedioxy; and R5 is hydrogen, C3 -C5 alkenyl, C1 -C3 alkyl, or phenyl C1 -C3 alkyl, and nontoxic, pharmaceutically acceptable addition salts thereof which have valuable pharmacological properties, particularly a long-lasting heart rate lowering effect and the effect of reducing the O2 requirement of the heart.

Emetic tetralones and the use thereof for inducing regurgitation

5,6-Dialkoxy-2-tetralones (I) are disclosed as useful intermediates in the synthesis of 2-amino-5,6-dialkoxytetralins (III) and 2-amino-5,6-dihydroxytetralins (IV). Compounds of the groups III and IV are potent emetics.

Cerebral dopamine agonist properties of some 2-aminotetralin derivatives after peripheral and intracerebral administration.

A series of variously N-substituted 2-aminotetralins having OH groups at 5 and 6 and at 6 and 7 positions, as well as nonoxygenated systems, has been evaluated for central dopaminergic effects. Stereotypical behavioral effects (sniffing, compulsive gnawing, and hyperactivity) produced by direct intracerebral administration of some of the agents were shown to differ strikingly from responses resulting from peripheral administration. The centrally mediated responses of hyperactivity and sterotypical gnawing-biting head and limb movements were shown to be separable in some test compounds. An improved route to 2-aminotetralin systems has been utilized for some of the compounds, which involves Pummerer rearrangement and cyclization of beta-keto sulfoxides and reductive amination of beta-tetralones with a NaBH4-carboxylic acid complex.

Synthesis and pharmacology of some 2 aminotetralins. Dopamine receptor agonists

A series of 2 amino 1,2,3,4 tetrahydronaphthalene compounds bearing substituents on the nitrogen and in the aromatic ring was synthesized from β tetralone intermediates. Compounds were screened in vivo for dopaminergic activity using tests in which apomorphine was especially active. It was found that apparent dopaminergic activity is inherent in 2 dialkylaminotetralins, the dipropylamine substitution being the most consistently productive amine group studied. Activity was greatly enhanced by proper substitution in the aromatic ring. The 5,6 dihydroxy group was the best potentiating group found. These data support the idea that the extended conformation for the phenylethylamine moiety of apomorphine and dopamine is favorable for dopaminergic agonist activity. They also suggest that an unetherified catechol group may not be essential for such activity.