349552-70-1

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 1-chloroisoquinoline-3-carboxylate is used as a building block in the production of various pharmaceuticals. Its reactivity and stability make it a valuable component in the synthesis of complex molecules for medicinal applications.
Used in Agrochemical Industry:
Methyl 1-chloroisoquinoline-3-carboxylate is also used in the synthesis of agrochemicals, contributing to the development of effective compounds for agricultural and pest control purposes.
Used in Organic Synthesis:
As a reactive intermediate, methyl 1-chloroisoquinoline-3-carboxylate is utilized in the construction of complex organic molecules, serving as a versatile precursor in various chemical reactions.

Upstream product

• 69454-42-8 methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate 
• 69454-42-8 1-hydroxyisoquinoline-3-carboxylic acid methyl ester 
• 119-67-5 o-carboxybenzaldehyde 
• 88590-43-6 4-(2-Methoxycarbonyl-benzyliden)-2-phenyl-oxazol-5-on 
• 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

• 910123-62-5 1-methylisoquinoline-3-carboxylic acid 
• 1049606-80-5 1-chloroisoquinoline-3-carboxylic acid 
• 1268691-09-3 N-(benzyl)-1-[3-(trifluoromethyl)phenylamino]-isoquinoline-3-carboxamide 
• 1268691-08-2 N-(cyclohexyl)-1-[3-(trifluoromethyl)-phenylamino]-isoquinoline-3-carboxamide 
• 1268691-07-1 N-(cyclohexylmethyl)-1-[3-(trifluoromethyl)-phenylamino]-isoquinoline-3-carboxamide 
• 1268691-06-0 methyl 1-[3-(trifluoromethyl)phenylamino]-isoquinoline-3-carboxylate 
• 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 academic research and scientific papers

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.

Structure activity relationship studies of 17-cyclopropylmethyl-3,14β- dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido) morphinan (NAQ) analogues as potent opioid receptor ligands: Preliminary results on the role of electronic characteristics for affinity and function

17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α- (isoquinoline-3′-carboxamido)morphinan (NAQ) was previously designed following the 'message-address' concept and was identified as a potent and highly selective mu opioid receptor (MOR) ligand based on its pharmacological profile. We here report the preliminary structure activity relationship (SAR) studies of this novel lead compound. For the new ligands synthesized as NAQ analogues, their binding assay results showed that a longer spacer and a saturated ring system of the side chain were unfavorable for their MOR selectivity over the kappa and delta opioid receptors. In contrast, substitutions with different electronic properties at either 1′- or 4′-position of the isoquinoline ring of the side chain were generally acceptable for reasonable MOR selectivity. The majority of NAQ analogues retained low efficacy at the MOR compared to NAQ in the 35S- GTP[γS] binding assays while electron-withdrawing groups at 1′-position of the isoquinoline ring induced higher MOR stimulation than electron-donating groups did. In summary, the electronic characteristics of substituents at 1′- or 4′-position of the isoquinoline ring in NAQ seem to be critical and need to be further tuned up to achieve higher MOR selectivity and lower MOR stimulation.

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.

COMPOUNDS FOR INDUCING CELLULAR APOPTOSIS

The present invention provides isoquinoline, tetrahydroisoquinoline and tetrahydropyridopyrimidine compounds that induce cell death by apoptosis and uses of the compounds in medicine, expecially their use for treating cancer and other diseases.

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.

Resolution and coupling of 1-(2′-hydroxy-1′-naphthyl)isoquinolines

The synthesis of bridged dimeric isoquinolylnaphthols has been developed. A simple method for the resolution of 1,1′-isoquinolyl-2′-naphthol permits measurement of the optical stability of the monomer, and in several cases slow racemisation at ambient temperature was observed. The enantiomeric stability is not greatly affected by steric buttressing. An unusual enhancement of the rate of atropisomerism is provided by the 3-bromomethylisoquinolines, and undermines the possibility of coupling pure enantiomeric components to provide a single stereoisomer of a tetradentate ligand.