143767-55-9

Usage

Uses

Used in Organic Synthesis:
DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate is used as a key intermediate in the synthesis of various organic compounds. Its versatile chemical structure allows for the creation of a wide range of derivatives, making it valuable in the development of new chemical entities.
Used in Pharmaceutical Research:
Due to its structural similarity to certain bioactive molecules, DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate is used as a starting material in the design and synthesis of new pharmaceutical agents. Its potential applications in medicine and pharmacology are currently under investigation, with the aim of identifying its therapeutic properties and possible uses in treating various diseases.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate is utilized as a scaffold for the development of novel drug candidates. Its unique structure provides a foundation for the attachment of various functional groups, enabling the creation of compounds with specific biological activities.
Further research is necessary to fully understand the properties and potential applications of DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate, as its current uses are primarily in the realm of organic synthesis and pharmaceutical research. As our understanding of DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate grows, it may find its way into various industries, including drug development, material science, and more.

Upstream product

• 67-56-1 methanol 
• 91-13-4 α,α'-dibromo-o-xylene 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 612-12-4 o-Xylylene dichloride 

Downstream Products

• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 143767-54-8 (R,S)-2-acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 151838-62-9 N-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 439287-42-0 3-(2,6-dimethyl-phenylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 74163-81-8 L-Tic-OH 
• 103733-65-9 (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 143767-56-0 (-)-menthyl (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 143767-57-1 (-)-menthyl (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 143767-56-0 (-)-menthyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores

Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(α-methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the α-methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg-1, TD50 = 36.4 mg kg-1, PI = 6.3). Replacement of the piperidine ring of 1 by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man.

Efficient synthesis of racemic and enantiomerically pure 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and esters

Racemic and optically pure 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids and esters were prepared, via base-catalyzed cyclization of 1,2-bis(halomethyl)benzenes 1a or b with diethyl 2-(acetylamino)malonate (2), subsequent decarboxylation and amide cleavage. The enantiomer resolution was achieved either by esterification with (-)-menthol followed by column chromatographic separation of the diastereomeric mixture or by diasteromeric salt separation of the benzylic ester with mandelic acid and base-catalyzed saponification of both esters.