844-25-7

Usage

Uses

Used in Bioimaging Applications:
1-CYANO-2-BENZOYL-1,2-DIHYDROISOQUINOLINE is used as a fluorescent marker for bioimaging applications. Its fluorescent properties allow researchers to visualize and track specific biological processes or structures within living organisms, aiding in the study of cellular dynamics and molecular interactions.
Used in Organic Synthesis:
In the field of organic synthesis, 1-CYANO-2-BENZOYL-1,2-DIHYDROISOQUINOLINE serves as a valuable intermediate or building block for the synthesis of more complex organic molecules. Its unique structure and functional groups make it a versatile component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
1-CYANO-2-BENZOYL-1,2-DIHYDROISOQUINOLINE is of interest to researchers in medicinal chemistry due to its potential pharmacological applications. Its structural features may contribute to the development of new drugs with specific therapeutic effects, such as targeting particular receptors or enzymes involved in disease pathways.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1-CYANO-2-BENZOYL-1,2-DIHYDROISOQUINOLINE is used as a key component in the development of new drugs. Its unique chemical properties and potential interactions with biological targets make it a promising candidate for the treatment of various diseases and medical conditions.
Used in Chemical Research:
1-CYANO-2-BENZOYL-1,2-DIHYDROISOQUINOLINE is utilized in chemical research to explore its properties, reactivity, and potential applications in various chemical processes. Understanding its behavior in different chemical environments can lead to the discovery of new reactions and the development of innovative synthetic methods.

InChI:InChI=1/C17H12N2O/c18-12-16-15-9-5-4-6-13(15)10-11-19(16)17(20)14-7-2-1-3-8-14/h1-11,16H

Upstream product

• 119-65-3 isoquinoline 
• 151-50-8 potassium cyanide 
• 143-33-9 sodium cyanide 
• 98-88-4 benzoyl chloride 
• 7677-24-9 trimethylsilyl cyanide 
• 5804-85-3 diethylaluminium cyanide 
• 2179-92-2 tri-n-butyltin cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 61206-56-2 N-benzoylisoquinolinium chloride 
• 138528-82-2 N-benzoylisoquinolinium triflate 

Downstream Products

• 384846-05-3 2-benzoyl-1-indol-3-ylmethyl-1,2-dihydro-isoquinoline-1-carbonitrile 
• 855645-35-1 3-(2-benzoyl-1-cyano-1,2-dihydro-[1]isoquinolylmethyl)-indole-2-carboxylic acid ethyl ester 
• 5467-83-4 1-[1]isoquinolyl-1-phenyl-ethanol 
• 5468-02-0 benzoyloxy-isoquinolin-1-yl-phenyl-methane 
• 5467-92-5 isoquinolin-1-yl(diphenyl)methanol 
• 102665-42-9 benzoic acid-([1]isoquinolyl-p-tolyl-methyl ester) 
• 54923-37-4 1-(α-benzoyloxy-4-chloro-benzyl)-isoquinoline 
• 102595-16-4 1-(α-benzoyloxy-2,6-dichloro-benzyl)-isoquinoline 
• 39971-70-5 1-(α-benzoyloxy-3,4-dimethoxy-benzyl)-isoquinoline 
• 102024-06-6 [1]isoquinolyl-phenyl-[2]thienyl-methanol 
• 102467-74-3 (4-chloro-phenyl)-[1]isoquinolyl-phenyl-methanol 
• 102594-30-9 [1]isoquinolyl-(4-methoxy-phenyl)-phenyl-methanol 
• 87365-05-7 ethyl 2-benzoyl-3-(1-isoquinolinyl)propionate 
• 1198-30-7 1-isoquinolinecarbonitrile 

Relevant academic research and scientific papers

Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca2+-activated K+ channel blockers

Starting from the scaffold of N-methyllaudanosine and N-methylnoscapine, which are known small conductance Ca2+-activated K+ channel blockers, original bis-isoquinolinium derivatives were synthezised and evaluated using binding studies, electrophysiology, and molecular modeling. These quaternary compounds are powerful blockers, and the most active ones have 10 times more affinity for the channels than dequalinium. The unsubstituted compounds possess a weaker affinity than the analogues having a 6,7-dimethoxy- or a 6,7,8-trimethoxy substitution. The length of the linker has no influence in the alkane derivatives. In relation to the xylene derivatives, the affinities are higher for the ortho and meta isomers. These results are well corroborated by a molecular modeling study. Finally, the most effective compounds have been tested in electrophysiological experiments on midbrain dopaminergic neurons and demonstrate the blocking potential of the apamin-sensitive after- hyperpolarization.

FUNGAL CELL WALL SYNTHESIS GENE

A reporter system reflecting the transport process that transports GPI-anchored proteins to the cell wall was constructed and compounds inhibiting this process were discovered. Further, genes conferring resistance to the above compounds were identified and methods of screening for compounds that inhibit the activity of the proteins encoded by these genes were developed.Therefore, through the novel compounds, the present invention showed that antifungal agents having a novel mechanism, i.e. inhibiting the process that transports GPI-anchored proteins to the cell wall, could be achieved.

Protoberberins from Reissert Compounds VI [1]. Diastereoselective Synthesis and Relative Configuration of 2-Benzoyl-1-cyano-1-(1-phenylalkyl)-1,2-dihydroisoquinolines

The alkylation of Reissert compounds 8 by sec-benzyl bromides 4, 7, and 10 diastereoselectively affords the title compounds 11 and 12. X-Ray structure analysis confirms an opposite configuration of the chiral centers in 11 and 12. The benzyl bromides 4, 7, and 10 are prepared by standard procedures.

Novel Cycloadditions of Isoquinoline Reissert Salts

Isoquinoline Reissert salts 5 partake in novel cycloadditions with acetylenic aldehydes 11 giving novel oxazoles 14 which have been characterised by X-ray crystallography.In contrast, closely related phthalazine Reissert salts 6 and phenanthridine Reissert salts 15 react by an alternative pathway giving pyrrolophthalazines 12 and pyrrolophenanthridines 16 respectively.

IMPROVED SYNTHESIS OF DIHYDROISOQUINOLINE REISSERT COMPOUNDS

Conversion of a series of 3,4-dihydroisoquinolines to their corresponding Reissert compounds was improved significantly over the usual reaction conditions by buffering the reaction medium at pH 8.

Reissert Compound Studies. LXIV. Reissert Compound and Other Products From an Isolated N-Benzoylisoquinolinium Triflate Salt

In the presence of trimethylsilyl trifluoromethanesulfonate, a methylene chloride solution of isoquinoline and benzoyl chloride gave N-benzoylisoquinolinium triflate (3) and N-H-isoquinolinium triflate (4).Depending on the reaction conditions, reaction of 3 may occur on the isoquinoline ring yielding a Reissert compound and 1,2-dihydroisoquinoline species.Otherwise, reactions transpire on the carbonyl of 3 to give an amide, an ester, and an anhydride.

REISSERT COMPOUND STUDIES LXIII: PREPARATION OF REISSERT COMPOUNDS USING DIETHYLALUMINIUM CYANIDE

Reissert compounds and analogs were synthesized from the reaction of acid halide, heterocyclic base and diethylaluminium cyanide.This new method of Reissert compound synthesis gave yields comparable to other synthetic routes.

Organic Sonochemistry. Synthesis and Use of Reissert Compounds under PTC-Ultrasound

Use of phase transfer catalysis and ultrasound stirring improved the synthesis, alkylation and hydrolysis of several Reissert derivatives.

REISSERT COMPOUND STUDIES. LIII. A NEW SYNTHESIS OF REISSERT COMPOUNDS USING TRI-n-BUTYLTIN CYANIDE

Reissert compounds were prepared by the reaction of the heterocyclic base and acyl halide with tri-n-butyltin cyanide in methylene chloride.

UTILIZATION OF ACETONE CYANOHYDRIN IN THE REISSERT REACTION

A modification of the Reissert reaction based on the utilization of acetone cyanohydrin instead of potassium cyanide is proposed.