607-32-9

Usage

Uses

Used in Organic Synthesis:
5-Nitroisoquinoline is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and functional groups make it a versatile building block in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Preparation of Pyrroloisoquinolines:
5-Nitroisoquinoline is specifically used in the synthesis of pyrroloisoquinolines, a class of fused heterocyclic compounds with potential applications in medicinal chemistry and drug discovery. The nitro group in 5-Nitroisoquinoline can be reduced or otherwise modified to form the pyrroloisoquinoline core, which can then be further functionalized to generate a diverse range of bioactive molecules with potential therapeutic properties.

InChI:InChI=1/C9H6N2O2/c12-11(13)9-3-1-2-7-6-10-5-4-8(7)9/h1-6H

Upstream product

• 119-65-3 isoquinoline 
• 118798-90-6 N-(2-Cyanoethyl)-5-nitroisoquinolinium cation 
• 57554-78-6 5-Nitroisoquinoline N-Oxide 
• 108-24-7 acetic anhydride 
• 708-14-5 phthalide-3-carboxylic acid 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 27810-64-6 isoquinoline-5-carboxylic acid 

Downstream Products

• 42792-95-0 2-methyl-5-nitroisoquinolin-2-ium iodide 
• 1125-60-6 isoquinolin-5-ylamine 
• 58142-46-4 4-bromo-5-nitro-isoquinoline 
• 65325-50-0 2-benzoyl-5-nitro-1,2-dihydro-isoquinoline-1-carbonitrile 
• 22950-00-1 2-benzoyl-5-nitro-1,2-dihydro-isoquinolin-1-ol 
• 147293-17-2 6-(methylamino)-5-nitroisoquinoline 
• 156901-61-0 8-amino-5-nitro-isoquinoline 
• 156901-44-9 8-(methylamino)-5-nitroisoquinoline 
• 109571-88-2 6-Phenyl-isoquinolin-5-ylamine 
• 109571-87-1 N-phenylisoquinolin-5-amine 
• 109571-89-3 6,8-Diphenyl-isoquinolin-5-ylamine 
• 603-11-2 3-nitrophthalic acid 
• 335391-43-0 trans-1,3-diallyl-5-nitro-1,2,3,4-tetrahydroisoquinoline 
• 41959-45-9 5-nitro-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of N1-(isoquinolin-5-yl)-N2-phenylpyrrolidine-1,2-dicarboxamide derivatives as potent TRPV1 antagonists

Reported herein is the design, synthesis, and pharmacologic evaluation of a class of TRPV1 antagonists constructed on a N1-(isoquinolin-5-yl)-N2-phenylpyrrolidine-1,2-dicarboxamide platform that evolved from a 5-aminoisoquinoline urea lead. Advancing the SAR of this series led to the eventual identification of 3b, comprising a p-Br substituted phenyl. In a TRPV1 functional assay, using cells expressing recombinant human TRPV1 channels, 3b displayed potent antagonism activated by capsaicin (IC50 = 0.084 μM) and protons (IC50 = 0.313 μM). In the preliminary analgesic and body temperature tests, 3b exhibited good efficacy in capsaicin-induced and heat-induced pain models and without hyperthermia side-effect. On the basis of its superior profiles, 3b could be considered as the lead candidate for the further development of antinociceptive drugs.

A Deprotonation Approach to the Unprecedented Amino-Trimethylenemethane Chemistry: Regio-, Diastereo-, and Enantioselective Synthesis of Complex Amino Cycles

The first realization of the amino-trimethylenemethane chemistry is reported using a deprotonation strategy to simplify the synthesis of the amino-trimethylenemethane donor in two steps from commercial and inexpensive materials. A broad scope of cycloaddition acceptors (seven different classes) participated in the chemistry, chemo-, regio-, diastereo-, and enantioselectively generating various types of highly valuable complex amino cycles. Multiple derivatization reactions that further elaborated the initial amino cycles were performed without isolation of the crude product. Ultimately, we applied the amino-trimethylenemethane chemistry to synthesize a potential pharmaceutical in 8 linear steps and 7.5 % overall yield, which previously was achieved in 18 linear steps and 0.6 % overall yield.

One substrate, two modes of C-H functionalization: A metal-controlled site-selectivity switch in C-H arylation reactions

A unique site-selectivity switch has been achieved in the ruthenium-catalyzed C-H arylation reaction of N-acetyl-1,2-dihydroisoquinolines. This metal-mediated switch is antipodal to the previous report on the palladium-mediated C-4 C-H arylation on the same substrate. Mechanistic details reveal interesting aspects of the reaction pathway, and kinetic studies bring out the difference in the modes of C-H activation adopted by the two catalytic systems.

Synthesis of Carbamide Derivatives Bearing Tetrahydroisoquinoline Moieties and Biological Evaluation as Analgesia Drugs in Mice

Transient receptor potential vanilloid 1 (TRPV1) is a ligand-gated non-selective cation channel that is considered to be an important pain integrator. Tetrahydroisoquinoline, the prototypical antagonist of TRPV1, has a clear therapeutic potential. Here, a series of carbamide derivatives of tetrahydroisoquinoline were designed and synthesized. Preliminary biological tests suggested that the compounds I 1, I 2, and I 9 had favorable TRPV1 antagonism activity. In further studies, I 1 exhibited better antinociceptive activity than the positive control BCTC in diverse pain models. All of these results suggested that I 1 can be considered as the lead candidate for the further development of antinociceptive drugs. A novel carbamide derivative of tetrahydroisoquinoline I 1 had impressive TRPV1 antagonism activity (89.02%), exerting potency similarity with the positive control BCTC. Moreover, in mice, I 1 could significantly inhibit the reaction to pain and nociception in three different pain models, and trigger the analgesic activity in a dose-dependent manner.

Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate

A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.

NOVEL ROCK INHIBITORS

The present invention relates to new kinase inhibitors of Formula (I), wherein X is oxygen, —NH—, or a direct bond; Y is —NH— or a direct bond; n is an integer from 0 to 4; m is an integer from 0 to 4; Cy represents a bivalent radical consisting of a satured (poly)cycle, including fused, bi-, spiro or bridged carbocycles and heterocycles; in particular selected from the group consisting of: Formula (II), Ar is selected from the group comprising: Formula (III), R2 is hydrogen or methyl; R8 is hydrogen, methyl, halogen, or alkynyl; R1 is an aryl or heteroaryl more specifically ROCK inhibitors, compositions, in particular pharmaceuticals, comprising such inhibitors, and to uses of such inhibitors in the treatment and prophylaxis of disease. In particular, the present invention relates to new ROCK inhibitors, compositions, in particular pharmaceuticals, comprising such inhibitors, and to uses of such inhibitors in the treatment and prophylaxis of disease. In addition, the invention relates to methods of treatment and use of said compounds in the manufacture of a medicament for the application to a number of therapeutic indications including sexual dysfunction, inflammatory diseases, ophthalmic diseases and Respiratory diseases.

NOVEL ROCK INHIBITORS

The present invention relates to new kinase inhibitors, more specifically ROCK inhibitors, compositions, in particular pharmaceuticals, comprising such inhibitors, and to uses of such inhibitors in the treatment and prophylaxis of disease. In particular, the present invention relates to new ROCK inhibitors, compositions, in particular pharmaceutic-als, comprising such inhibitors, and to uses of such inhibitors in the treatment and prophylaxis of disease. In addition, the invention relates to methods of treatment and use of said compounds in the manufacture of a medicament for the ap-plication to a number of therapeutic indications including sexual dysfunction, inflammatory diseases, ophthalmic dis-eases and Respiratory diseases. Compounds of the invention display soft drug characteristics, i.e. they are rapidly inactivated upon entry in the systemic circulation. Therefore, they allow for reduced systemic exposure to functionally active ROCK inhibitors

Synthesis and cytotoxicity studies of some new amino isoquinolin-5,8-dione and quinolin-5,8-dione derivatives

During the search for new cytotoxic drugs, a new series of 7-amino-isoquinoline-5,8-dione and 6-amino-quinoline-5,8-dione derivatives have been synthesised starting from isoquinoline, and 8-hydroxy-quinoline, respectively, through multistep reactions. The title compounds 7-amino-isoquinoline-5,8-diones have been prepared by treatment of 6-bromoisoquinoline-5,8-dione with some alkyl/heterocyclic/aromatic amines via nucleophilic tetrahedral mechanism. On the other hand, the corresponding 6-amino-quinoline-5,8-diones have been prepared by treating 7-bromo-quinoline-5, 8-dione with some alkyl/heterocyclic/aromatic amines. Rate of reactions depend on the electron availability on the served aminocompounds (i.e. alkyl/heterocyclic/aromatic amines) during their reactions with the corresponding isoquinoline and quinoline quinones. All synthesised compounds have been purified using a series of chromatographic techniques, and their structures have been characterized by NMR spectroscopy and high resolution EI mass spectrometry. The newly synthesised compounds have been evaluated for cytotoxicity using brine shrimps, demonstrating potent cytotoxic activity (95-100%).

NOVEL ROCK INHIBITORS

The present invention relates to new kinase inhibitors, more specifically ROCK inhibitors, compositions, in particular pharmaceuticals, comprising such inhibitors, and to uses of such inhibitors in the treatment and prophylaxis of disease. In particular, the present invention relates to new ROCK inhibitors, compositions, in particular pharmaceuticals, comprising such inhibitors, and to uses of such inhibitors in the treatment and prophylaxis of disease. In addition, the invention relates to methods of treatment and use of said compounds in the manufacture of a medicament for the application to a number of therapeutic indications including sexual dysfunction, inflammatory diseases, ophthalmic diseases and Respiratory diseases.

Synthesis, cytotoxic activities and structure-activity relationships of topoisomerase I inhibitors: Indolizinoquinoline-5,12-dione derivatives

A series of indolizinoquinoline-5,12-dione derivatives (IQDs) are synthesized and evaluated for their cytotoxic activities toward human lung adenocarcinoma (GLC-82), large-cell lung carcinoma (NCI-H460), promyelocytic leukemia (HL-60) and breast carcinoma (MCF-7) cells by MTT method. Most of the IQDs show significant cytotoxic potency. In addition, the evaluation of structure-activity relationships indicated that the incorporation of electron-withdrawing substituents at the C or D ring will enhance the activities of the target compounds distinctly. The topoisomerase I inhibitory activity is also measured.