Dopamine agonists: structure-activity relationships

Cannon, Joseph G.

doi:10.1007/978-3-0348-9315-2_9

Cited by 57 publications

(25 citation statements)

References 238 publications

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“…± Dopamine (1) [1], a hormone-like substance, is an important neurotransmitter. When present in normal quantities, it facilitates critical brain functions.…”

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confidence: 99%

A Concise Synthesis of 2‐Amino‐1,2,3,4‐tetrahydronaphthalene‐6,7‐diol (‘6,7‐ADTN’) from Naphthalene‐2,3‐diol

Göksu¹,

Kazaz²,

Sütbeyaz³

et al. 2003

Helvetica Chimica Acta

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2-Amino-1,2,3,4-tetrahydronaphthalene-6,7-diol (2; 6,7-ADTN) was synthesized starting from naphthalene-2,3-diol in seven steps and with an overall yield of 44%. Methylation of naphthalene-2,3-diol with dimethyl sulfate, followed by FriedelÀCrafts acylation with AcCl, gave 2-acetyl-6,7-dimethoxynaphthalene. 2-Acetyl-6,7-dimethoxynaphthalene was converted to 6,7-dimethoxynaphthalene-2-carboxylic acid by a haloform reaction. Birch reduction of the carboxylic acid with 4 mol-equiv. of Na in liquid ammonia afforded 1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-carboxylic acid, from which 2 was obtained by a Curtius reaction, followed by hydrogenolysis and demethylation.

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“…± Dopamine (1) [1], a hormone-like substance, is an important neurotransmitter. When present in normal quantities, it facilitates critical brain functions.…”

mentioning

confidence: 99%

A Concise Synthesis of 2‐Amino‐1,2,3,4‐tetrahydronaphthalene‐6,7‐diol (‘6,7‐ADTN’) from Naphthalene‐2,3‐diol

Göksu¹,

Kazaz²,

Sütbeyaz³

et al. 2003

Helvetica Chimica Acta

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“…The ester 6 was also prepared with an overall yield 66% by a different procedure by Perrone and collaborators. 9 Bromination of the ester 6 with NBS and dimethylformamide yielded the compound 7 in 67% yield as evidenced by 1 H NMR spectroscopy. The formation of the two doublets at δ 6.71 and δ 7.01 ppm (see experimental) for compound 7 corresponding to the protons at C-7 and C-8 corroborates the presence of bromine at the position C-5.…”

Section: Resultsmentioning

confidence: 95%

A new synthesis of 5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Chinea¹,

Banerjee²

2016

Arkivoc

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“…It has been suggested that 6,7-ADTN (3), a dopamine-like compound, interacts with the dopamine receptor with slightly greater affinity than dopamine itself. Cannon et al have synthesized a series of 2-amino-4,5-dihydroxyindans, including compounds 2, 4, and reported that certain N-alkylated 4,5-dihydroxyindanes were violent emetics in the dog, and were potent in blockade of the effect of stimulation of the cardioaccelarator nerve in the cat 20 . Aminoindan 2 has been reported to have adrenergic effects 21 and covalent binding 22 to Src family SH2 domains.…”

Section: Research Articlementioning

confidence: 99%