143767-55-9

Basic information

• Product Name: DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate
• Synonyms: DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate
• CAS NO: 143767-55-9
• Molecular Formula: C₁₅H₁₇NO₅
• Molecular Weight: 290.29124
• EINECS: -0
• Mol File: 143767-55-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate(143767-55-9)
• EPA Substance Registry System: DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate(143767-55-9)

Safety Data

• Hazardous Substances Data: 143767-55-9(Hazardous Substances Data)

Usage

General Description

DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate is a chemical compound with the molecular formula C17H17NO6. It is a diester derivative of isoquinoline and is commonly used in organic synthesis. DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate has potential pharmaceutical applications due to its structural similarity to certain bioactive molecules. It may also have other uses in the fields of medicine and pharmacology. However, further research is needed to fully understand the properties and potential applications of DiMethyl 2-Acetyl-1,2-dihydroisoquinoline-3,3(4H)-dicarboxylate.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.