27104-73-0

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-isoquinolinecarboxylate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to be converted into other bioactive molecules makes it a valuable component in the development of new drugs.
Used in Chemical Synthesis:
Methyl 3-isoquinolinecarboxylate serves as a key building block in the preparation of various organic compounds, including 3-acetylisoquinoline. This application takes advantage of its reactivity and structural features to create a wide range of products with diverse properties and potential uses.
Used in Research and Development:
Due to its unique chemical structure, Methyl 3-isoquinolinecarboxylate is utilized in research and development for the exploration of new chemical reactions, synthesis methods, and potential applications in various fields, including material science, pharmaceuticals, and agrochemicals.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 1081, 1982 DOI: 10.1021/jm00351a015

InChI:InChI=1/C11H9NO2/c1-14-11(13)10-6-8-4-2-3-5-9(8)7-12-10/h2-7H,1H3

Upstream product

• 57060-86-3 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 124300-67-0 o-butadienyl α-azidocinnamate 
• 89524-99-2 methyl 2-acetylamino-2-(dimethoxyphosphinyl)acetate 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 67-56-1 methanol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 35356-70-8 Methyl 2-acetamidoacrylate 
• 26260-02-6 2-iodobenzaldehyde 
• 5429-56-1 N-Acetamidoacrylic acid 
• 124-41-4 sodium methylate 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 44804-84-4 2-(formamido)acrylic acid methyl ester 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 5535-48-8 PVS 

Downstream Products

• 91544-03-5 3-acetylisoquinoline 
• 1323137-94-5 C₁₃H₁₃NO₃ 
• 106662-18-4 methyl 1-cyclohexylisoquinoline-3-carboxylate 

Relevant academic research and scientific papers

A new (3+3) annulation route to isoquinoline-3-carboxylates

A new synthesis of isoquinoline-3-carboxylates based on the palladium(0)-catalysed Heck-type arylation of 2-amidoacrylates with the appropriate 2-substituted iodobenzene is reported.

β-Carbolines: Synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors

The authors have prepared a series of tetrahydro-β-carbolines (THβC), β-carbolines (β-C), and other nitrogen heterocycles and evaluated them in vitro with respect to their ability to bind to benzodiazepine receptors. The fully aromatic β-C's were more pot

Palladium-catalysed cascades triggered by dehydrogenation of secondary or tertiary amines: Access to bridged- and fused-ring heterocycles

Palladium-catalysed cascades triggered by dehydrogenation of secondary or tertiary amines and trapping the intermediate imines with cycloadditions and Mannich reactions result in a range of bridged- and fused-ring heterocyclic motifs in moderate to good y

Synthesis and assay of isoquinoline derivatives as HIV-1 Tat-TAR interaction inhibitors

Four new isoquinoline derivatives bearing guanidinium group or amino group-terminated side chain were synthesized to target the HIV-1 TAR element. Their abilities to bind TAR RNA and inhibit Tat-TAR RNA interaction were determined by CE analysis, a Tat-dependent HIV-1 LTR-driven CAT assay and SIV-induced syncytium evaluation.

A chromone hydrazide Schiff base fluorescence probe with high selectivity and sensitivity for the detection and discrimination of human serum albumin (HSA) and bovine serum albumin (BSA)

The discrimination and identification of human serum albumin (HSA) and bovine serum albumin (BSA) is very important, which is due to the vital roles of two SAs in biological and pharmaceutical research. Based on structural screening and docking calculation from a series of homologues, a coumarin Schiff base fluorescent probe 3-hydroxy-N′-((4-oxo-4H-chromen-3-yl)methylene)-2-naphthohydrazide (HCNH) has been designed and synthesized, which could effectively discriminate HSA and BSA. The probe HCNH exhibited superior sensitivity toward HSA and BSA with the detection limits of 10.62 nM and 16.03 nM in PBS solution, respectively. The binding mechanism of HCNH with SAs was studied by Job's plot analysis, SA destruction and displacement assay. Molecular docking and DFT methods were utilized to provide deep insight into the spatial conformation change of HCNH and binding sites in HSA/BSA. The conformation of HCNH was significantly influenced by the microenvironment provided by HSA and BSA, therefore its fluorescence emission was affected correspondingly. Non-toxic probe HCNH could be successfully used for fluorescence bio-imaging of HSA in cancer cells, which is significantly different from normal cells and favors the application in medical diagnosis.

Electrochemical Deoxygenation of N-Heteroaromatic N -Oxides

An electrochemical method for the deoxygenation of N-heteroaromatic N -oxide to give the corresponding N-heteroaromatics has been developed. Several classes of N-heterocycles such as pyridine, quinoline, isoquinoline, and phenanthridine are tolerated. The electrochemical reactions proceed efficiently in aqueous solution without the need for transition-metal catalysts and waste-generating reducing reagents.

Design and Discovery of Novel Chiral Antifungal Amides with 2-(2-Oxazolinyl)aniline as a Promising Pharmacophore

Inspired by established succinate dehydrogenase inhibitors (SDHIs), our continuing efforts toward the discovery of chiral antifungal amides turned to the optimization of their polar regions with 2-(2-oxazolinyl)aniline as a known pharmacophore. Scaffold hopping and bioactivity-guided convergent synthesis enabled the identification of promising antifungal categories. Fine tuning of the substituents and chirality furnished seven amides (1s, 1t, 2d, 2h, 2j, 3k, and 2l) as antifungal candidates, with EC50 values lower than 5 mg/L. The first investigation of chiral amides of acyclic acids as SDHIs was conducted, and compound 2d was selected as a promising candidate against Botrytis cinerea, with a preventative efficacy of up to 93.9% at 50 mg/L, which is better than that of boscalid. The different binding models between compounds with different configurations were simulated for compound 2d and its diastereoisomers. The benefits of synthetic accessibility and cost-effectiveness highlight the practical potential for compound 2d as a good alternative to known SDHI fungicides.

Gene delivery system

The invention discloses a preparation method of a gene nano-liposome carrier Isoquinoline-3-acyl-RGDV(IRV) and an IRV/STAT3-siRNA gene delivery system. The IRV/STAT3-siRNA gene delivery system is composed of liposome carriers IRV and STAT3-siRNA, protamine and calf thymus DNA in a proportion, and has slow release and targeting effects. The cell transfection efficiency, the in-vitro anti-tumor activity, and the gene silencing efficiency and a cell action mechanism on the mRNA level and the protein level of a compound are evaluated with the lung cancer A549 cell strain as a model, and the result shows the IRV/STAT3-siRNA gene delivery system has more excellent anti-tumor activity and gene silencing efficiency compared with control groups. According to the system, the anti-tumor activity of the IRV/STAT3-siRNA gene delivery system is evaluated with an S180 ascites tumor mouse as a model, and the result shows that a 100% IRV/STAT3-siRNA group has an anti-tumor effect.

Imidazole-containing condensed tricyclic compound and application thereof

The invention discloses an imidazole-containing condensed tricyclic compound adopting the structure as shown in the formula (I) or pharmaceutically acceptable salts, stereisomers or prodrug molecules thereof. The imidazole-containing condensed tricyclic compound has the IDO1 activity regulation function, can enhance T-cell activation through blocking immune checkpoints IDO1, is used for treating IDO1-mediated immunosuppression, and therefore, can become an effective medicine for treating malignant tumors. When used together with checkpoint protein anti-body drugs or other anti-cancer drugs, the imidazole-containing condensed tricyclic compound can enhance the anti-cancer effect. Meanwhile, the imidazole-containing condensed tricyclic compound has the potential of effectively treating IDO1 abnormity related immunosuppressive diseases and has a high application value.

Development of a metal-free amine oxidation method utilizing DEAD chemistry

Herein, we examine the oxidative abilities of azodicarboxylates for the conversion of amines to imines. This method provides access to synthetically useful imine intermediates including β-carbolines, quinazolines and N-heterocyclic carbene precursors. The ability to recover spent azodicarboxylate for regeneration and further use underscores the applicability and appeal of this protocol.