13221-89-1Relevant articles and documents
Synthetic method of arecoline
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Paragraph 0032; 0036-0038; 0045; 0048-0049, (2021/04/26)
The invention discloses a synthetic method of arecoline. The synthetic method comprises the following steps: taking methyl 3-bromopropionate as an initial raw material, sequentially carrying out sodium methoxide claisen ester condensation, methylamine cyclization, sodium borohydride reduction and dehydration under alkaline conditions to obtain arecoline. According to the method, methyl 3-bromopropionate and a methylamine alcohol solution are used as the raw materials so that the problem that methyl iodide or highly toxic dimethyl sulfate with high cost is used in an N-methylation step, and the safety is controlled from the source is avoided.
Essential structure of opioid κ receptor agonist nalfurafine for binding to κ receptor 1: Synthesis of decahydroisoquinoline derivatives and their pharmacologies
Nagase, Hiroshi,Imaide, Satomi,Yamada, Takaaki,Hirayama, Shigeto,Nemoto, Toru,Yamaotsu, Noriyuki,Hirono, Shuichi,Fujii, Hideaki
scheme or table, p. 945 - 948 (2012/10/18)
On the basis of the three-dimensional pharmacophore model of opioid κ agonists, we simplified the structure of nalfurafine (selective κ agonist) to find the essential structural moieties for binding the opioid receptors, especially κ receptor type. As a result, we found that the trans-fused decahydroisoquinoline derivatives without a phenol ring bound the opioid receptor in micromolar order and that both the amide side chain and the nitrogen substituted by the cyclopropylmethyl group were indispensable moieties for eliciting the κ selectivity. The simple decahydroisoquinoline without amide side chain also bound the opioid receptor without receptor type selectivity, suggesting that the message-address concept would be applicable to even these simple derivatives. These findings that the simple decahydroisoquinoline derivatives showed the affinities for the opioid receptors, especially some of the compounds showed κ selectivity, are the first example in the opioid field.
