349552-70-1

Basic information

• Product Name: methyl 1-chloroisoquinoline-3-carboxylate
• Synonyms: methyl 1-chloroisoquinoline-3-carboxylate
• CAS NO: 349552-70-1
• Molecular Formula: C₁₁H₈ClNO₂
• Molecular Weight: 222
• Mol File: 349552-70-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: methyl 1-chloroisoquinoline-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-chloroisoquinoline-3-carboxylate(349552-70-1)
• EPA Substance Registry System: methyl 1-chloroisoquinoline-3-carboxylate(349552-70-1)

Safety Data

• Hazardous Substances Data: 349552-70-1(Hazardous Substances Data)

Usage

General Description

Methyl 1-chloroisoquinoline-3-carboxylate is a chemical compound with the molecular formula C12H8ClNO2. It is a derivative of isoquinoline, which is a heterocyclic aromatic compound commonly found in nature. This chemical is used in organic synthesis as a building block for the production of various pharmaceuticals and agrochemicals. The chloro group on the isoquinoline ring makes it a reactive intermediate in chemical reactions, allowing it to be used in the construction of complex molecules. Additionally, the ester functional group provides stability to the molecule, making it a useful precursor in the synthesis of various other organic compounds.

Upstream product

• 69454-42-8 methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate 
• 69454-42-8 1-hydroxyisoquinoline-3-carboxylic acid methyl ester 
• 88590-43-6 4-(2-Methoxycarbonyl-benzyliden)-2-phenyl-oxazol-5-on 
• 119-67-5 o-carboxybenzaldehyde 
• 4122-56-9 methyl o-formylbenzoate 
• 23364-15-0 (DL)-methyl 1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 63586-82-3 1-Oxo-1,2,3,4-tetrahydro-3(R,S)-isoquinolinecarboxylic Acid 

Downstream Products

• 1268691-06-0 methyl 1-[3-(trifluoromethyl)phenylamino]-isoquinoline-3-carboxylate 
• 1268691-07-1 N-(cyclohexylmethyl)-1-[3-(trifluoromethyl)-phenylamino]-isoquinoline-3-carboxamide 
• 1268691-08-2 N-(cyclohexyl)-1-[3-(trifluoromethyl)-phenylamino]-isoquinoline-3-carboxamide 
• 1268691-09-3 N-(benzyl)-1-[3-(trifluoromethyl)phenylamino]-isoquinoline-3-carboxamide 
• 910123-62-5 1-methylisoquinoline-3-carboxylic acid 
• 1049606-80-5 1-chloroisoquinoline-3-carboxylic acid 
• 1443759-14-5 3-(1-cyclopropyl-isoquinoline-3-carbonyl)-2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester 
• 1253385-93-1 methyl 1-(2-fluorophenyl)isoquinoline-3-carboxylate 

Relevant articles and documents

Design, syntheses, and pharmacological characterization of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido)morphinan analogues as opioid receptor ligands

A series of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido)morphinan (NAQ) analogues were synthesized and pharmacologically characterized to study their structure-activity relationship at the mu opioid receptor (MOR). The competition binding assay showed two-atom spacer and aromatic side chain were optimal for MOR selectivity. Meanwhile, substitutions at the 1′- and/or 4′-position of the isoquinoline ring retained or improved MOR selectivity over the kappa opioid receptor while still possessing above 20-fold MOR selectivity over the delta opioid receptor. In contrast, substitutions at the 6′- and/or 7′-position of the isoquinoline ring reduced MOR selectivity as well as MOR efficacy. Among this series of ligands, compound 11 acted as an antagonist when challenged with morphine in warm-water tail immersion assay and produced less significant withdrawal symptoms compared to naltrexone in morphine-pelleted mice. Compound 11 also antagonized the intracellular Ca2+ increase induced by DAMGO. Molecular dynamics simulation studies of 11 in three opioid receptors indicated orientation of the 6′-nitro group varied significantly in the different 'address' domains of the receptors and played a crucial role in the observed binding affinities and selectivity. Collectively, the current findings provide valuable insights for future development of NAQ-based MOR selective ligands.

Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists

Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.

Synthetic approaches to 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid

In connection with our research of new antitumor compounds, previously undescribed approaches to the 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid 9 are reported here. Two related accesses from phenylethylamine or amphetamine were investigated and were found to be successful. A more robust synthesis, using Suzuki's cross-coupling between 2-chlorophenylboronic acid 15 and the previously unreported methyl-1-bromoisoquinoline-3-carboxylate 14 was also developed. This synthetic route provides the ground for a combinatorial approach to the core structure of new potential peripheral benzodiazepine receptor ligands.