80278-67-7

Usage

Uses

Used in Organic Synthesis:
ISOQUINOLINE-5-CARBALDEHYDE is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity allows for a wide range of chemical transformations, such as reduction, oxidation, and condensation reactions, enabling the formation of diverse molecular structures.
Used in the Direct Conversion of Heteroaryl-carboxaldehydes:
ISOQUINOLINE-5-CARBALDEHYDE is used as a reactant in the direct conversion of heteroaryl-carboxaldehydes to acetonitriles. This process involves the treatment of heteroaryl-carboxaldehydes with cyanoethylphosphonate, followed by samarium(II) iodide reduction. This method provides a convenient and efficient route to synthesize acetonitriles, which are valuable building blocks in organic chemistry and have applications in the synthesis of various pharmaceuticals and agrochemicals.

InChI:InChI=1/C10H7NO/c12-7-9-3-1-2-8-6-11-5-4-10(8)9/h1-7H

Upstream product

• 34784-04-8 5-bromoisoquinoline 
• 68-12-2 N,N-dimethyl-formamide 
• 1532-71-4 1-bromoisoquinoline 
• 857822-30-1 2-(2-methylphenyl)ethylformamide 
• 100643-54-7 5-methyl-3,4-dihydro-isoquinoline 
• 16675-59-5 methyl isoquinoline-5-carboxylate 
• 62882-01-3 5-methylisoquinoline 
• 119-65-3 isoquinoline 

Downstream Products

• 308110-26-1 N,N-diethyl-4-[hydroxy(5-isoquinolinyl)methyl]benzamide 
• 1198319-66-2 (S)-6-benzyl-4-(cyclopropanecarbonyl)-2-(2-(1-(isoquinolin-5-ylmethyl)piperidin-4-yl)ethyl)-4,5,6,7-tetrahydropyrazolo[4,3-e][1,4]diazepin-8(2H)-one 
• 1428968-31-3 1-(1H-indol-3-yl)-2-(isoquinolin-5-yl)-2-((3-methoxyphenyl)amino)ethanone 
• 54415-44-0 1-isoquinolin-5-yl-ethanone 
• 158654-74-1 5-(bromomethyl)isoquinoline 
• 119-65-3 isoquinoline 
• 16675-59-5 methyl isoquinoline-5-carboxylate 

Relevant academic research and scientific papers

PROCESS FOR PREPARING A COT INHIBITOR COMPOUND

Disclosed are syntheses of a Cot (cancer Osaka thyroid) inhibitor, which has the formula (I).

ISOQUINOLINE COMPOUNDS, A PROCESS FOR THEIR PREPARATION, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

A compound of formula (I): wherein the substituents are as defined in the description. Medicinal products containing the same which are useful in treating or preventing pathologies which are the result of activation of the RhoA/ROCK pathway and phosphorylation of the myosin light chain.

Co-administration of dopamine-receptor binding compounds

Methods for treating a patient having neurological, psychotic, and psychiatric disorders are described comprising the steps of administering to the patient an effective amount of a partial and/or full dopamine D1 receptor agonist, and administering to the patient an effective amount of a dopamine D2 receptor antagonist. Pharmaceutical compositions comprising a dopamine D1 receptor agonist and a dopamine D2 receptor antagonist are also described. The D1 dopamine receptor agonist and the D2 dopamine receptor antagonist can be administered to the patient in the same or in a different composition or compositions.

METHOD OF ADMINISTRATION OF DOPAMINE RECEPTOR AGONISTS

Methods for treating a patient having pulmonary edema are described. The methods include administering to the lung endobronchial space of the airways of the patient an effective amount of a dopamine D1 receptor agonist. Dopamine D1 receptor agonists, including hexahydrobenzophenanthridine, hexahydrothienophenanthridine, phenylbenzodiazepine, chromenoisoquinoline, naphthoisoquinoline dopamine receptor agonists, and their pharmaceutically acceptable salts, formulated as aerosols and dry powders are also described.

Process for the preparation of dinaposoline

The present invention relates to a novel process for the preparation of compounds of the formula wherein R1, R2, R4, R5, R6and A are as defined herein, and to certain derivations of Formula IX which are useful for the treatment of movement disorders.

(+)-Dinapsoline: An efficient synthesis and pharmacological profile of a novel dopamine agonist

A highly convergent synthesis was developed for the novel dopamine agonist dinapsoline (12) (Ghosh, D.; Snyder, S. E.; Watts, V. J.; Mailman, R. B.; Nichols, D. E. 8,9-Dihydroxy-2,3,7, 11b-tetrahydro-1H-naph[1,2,3-de]isoquinoline: A Potent Full Dopamine D1 Agonist Containing a Rigid β-Phenyldopamine Pharmacophore. J. Med. Chem. 1996, 39 (2), 549-555). The crucial step in the new synthesis was a free radical-initiated cyclization to give the complete dinapsoline framework. The improved synthesis required half as many steps as the original procedure (Nichols, D. E.; Mailman, R.; Ghosh, D. Preparation of novel naphtho[1,2,3-de]isoquinolines as dopamine receptor ligands. PCT Int. Appl. WO 9706799 A1, Feb 27, 1997). One of the late-stage intermediates (11) was resolved into a pair of enantiomers. From there, the (R)-(+)-12 (absolute configuration by x-ray) of dinapsoline was identified as the active enantiomer. In unilateral 6-hydroxydopamine (6-OHDA)-lesioned rats, (+)-dinapsoline showed robust rotational behavior comparable to that of an external benchmark, trans- 4,5,5a,6,7,11b-hexahydro-2-propylbenzo[f]thieno[2,3-c]quinoline-9,10-diol, hydrochloride 18 (Michaelides, M. R.; Hong, Y. Preparation of heterotetracyclic compounds as dopamine agonists. PCT Int. Appl. WO 9422858 A1, Oct 13, 1994).

New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability

Nonpeptide δ opioid agonists are analgesics with a potentially improved side-effect and abuse liability profile, compared to classical opioids. Andrews analysis of the NIH nonpeptide lead SNC-80 suggested the removal of substituents not predicted to contribute to binding. This approach led to a simplified lead, N,N-diethyl-4-[phenyl(1-piperazinyl)methyl]benzamide (1), which retained potent binding affinity and selectivity to the human δ receptor (IC50 = 11 nM, μ/δ = 740, κ/δ > 900) and potency as a full agonist (EC50 = 36 nM) but had a markedly reduced molecular weight, only one chiral center, and increased in vitro metabolic stability. From this lead, the key pharmacophore groups for δ receptor affinity and activation were more clearly defined by SAR and mutagenesis studies. Further structural modifications on the basis of 1 confirmed the importance of the N,N-diethylbenzamide group and the piperazine lower basic nitrogen for δ binding, in agreement with mutagenesis data. A number of piperazine N-alkyl substituents were tolerated. In contrast, modifications of the phenyl group led to the discovery of a series of diarylmethylpiperazines exemplified by N,N-diethyl-4-[1-piperazinyl(8-quinolinyl)-methyl]benzamide (56) which had an improved in vitro binding profile (IC50 = 0.5 nM, μ/δ = 1239, EC50 = 3.6 nM) and increased in vitro metabolic stability compared to SNC-80.