73554-57-1Relevant academic research and scientific papers
Synthesis method of 5'-methoxyl laudanosine
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Paragraph 0035-0039; 0043-0046; 0049-0052; 0055-0058; ..., (2021/11/10)
The invention discloses a synthesis method of 5'-methoxyl laudanthin, belonging to the technical field of organic synthesis. According to the method, 3,4-dimethoxyphenylethylamine and 3,4,5-trimethoxyphenylacetaldehyde are used as initial raw materials through an optimized process by utilizing the Pictet-Spengler reaction, dichloromethane is used as a solvent, and under the catalysis of a transition metal lewis acid catalyst, a dehydration reaction is performed through a dehydrating agent at 23-27 DEG C, or refluxing is performed in formic acid and phosphorus pentoxide is used for dehydration; and synthesized 6,7-dimethoxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolinen reacts with a methyl donor by using formic acid as a solvent to obtain 5'-methoxy laudanosine. According to a technical scheme in the invention, a synthetic route is short in step, toxic and harmful reagents including phosphorus oxychloride and methylbenzene are not used, the steps of hydrogenation reduction and the like are avoided, total reaction yield is high, the obtained 5'-methoxy laudanin is high in purity, process cost is low, a process is environmentally friendly, process operation is simple, and the method has actual production value and can be used for industrial production.
Effect of 1-Substitution on Tetrahydroisoquinolines as Selective Antagonists for the Orexin-1 Receptor
Perrey, David A.,German, Nadezhda A.,Decker, Ann M.,Thorn, David,Li, Jun-Xu,Gilmour, Brian P.,Thomas, Brian F.,Harris, Danni L.,Runyon, Scott P.,Zhang, Yanan
, p. 599 - 614 (2015/04/27)
Selective blockade of the orexin-1 receptor (OX1) has been suggested as a potential approach to drug addiction therapy because of its role in modulating the brain's reward system. We have recently reported a series of tetrahydroisoquinoline-based OX1 selective antagonists. Aimed at elucidating structure-activity relationship requirements in other regions of the molecule and further enhancing OX1 potency and selectivity, we have designed and synthesized a series of analogues bearing a variety of substituents at the 1-position of the tetrahydroisoquinoline. The results show that an optimally substituted benzyl group is required for activity at the OX1 receptor. Several compounds with improved potency and/or selectivity have been identified. When combined with structural modifications that were previously found to improve selectivity, we have identified compound 73 (RTIOX-251) with an apparent dissociation constant (Ke) of 16.1 nM at the OX1 receptor and >620-fold selectivity over the OX2 receptor. In vivo, compound 73 was shown to block the development of locomotor sensitization to cocaine in rats. (Chemical Equation Presented).
Synthesis of 8-oxoberbines and related benzolactams by Pd(OAc) 2-catalyzed direct aromatic carbonylation
Miyazawa, Mamoru,Tokuhashi, Takashi,Horibata, Akiyoshi,Nakamura, Takatoshi,Onozaki, Yu,Kurono, Nobuhito,Senboku, Hisanori,Tokuda, Masao,Ohkuma, Takeshi,Orito, Kazuhiko
, p. E48-E54 (2013/06/05)
A variety of alkoxy-substituted benzolactams with a berbine or yohimbane skeleton were prepared from 1-benzyl-1,2,3,4-tetrahydroisoquinolines or 1-benzyl-1,2,3,4-tetrahydro-β-carbolines by a phosphine-free Pd(II)-catalyzed direct aromatic carbonylation in a Pd(OAc)2-Cu(OAc) 2 catalytic system. The site selectivity was compared with that of the carbonylation with Pd(OAc)2 or Pd(OAc)2·2 PPh3, respectively.
Studies on Protoberberine Alkaloids : Synthesis of Glabrine Dimethyl Ether
Patra, Amarendra,Mukhopadhyay, Prabir K.,Mitra, Alok K.
, p. 561 - 562 (2007/10/02)
2,3,9,10,11-Pentamethoxyprotoberberinium salt (III) has been synthesized from homoveratrylamine and 3,4,5-trimethoxyphenylacetic acid through the intermediacy of an N-formyl-benzyltetrahydroisoquinoline derivative (VI).The synthetic material is identical
