54978-07-3

Usage

General Description

1-Naphthalenecarbonyl chloride, 3-nitro- is a chemical compound with the formula C11H6ClNO3. It is a derivative of naphthalene and is typically used in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. 1-Naphthalenecarbonyl chloride, 3-nitro- is known for its reactivity as an acyl chloride, making it useful in the formation of amides, esters, and other organic compounds. Additionally, the 3-nitro group on the naphthalene ring provides unique reactivity that can be harnessed for various chemical transformations. Overall, 1-Naphthalenecarbonyl chloride, 3-nitro- plays a crucial role in the field of organic chemistry and is valued for its versatile and valuable chemical properties.

Upstream product

• 4507-84-0 3-nitro-1-naphthoic acid 

Downstream Products

• 95092-65-2 phenyl 3-nitro-1-naphthoate 
• 255050-54-5 N-[2-(4-chlorophenyl)-4-hydroxybutyl]-N-methyl-3-nitro-1-naphthalenecarboxamide 
• 255049-73-1 N-[(S)-2-(3,4-Dichlorophenyl)-4-[4-[2-trifluoromethylphenyl]-1-piperidinyl]butyl]-N-methyl-3-nitronaphthamide Citrate 
• 255050-11-4 N-[(S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methyl-3-nitro-1-naphthalenecarboxamide 
• 79996-92-2 (3-bromonaphthalen-1-yl)methanol 
• 16650-63-8 3-bromo-naphthalene-1-carboxylic acid methyl ester 
• 954410-06-1 [(2S)-1-{[1-(3-ethoxyphenyl)-2-(2-fluoro-4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-4-(4-{[(triisopropylsilyl)oxy]methyl}-2-naphthyl)piperazin-2-yl]methyl acetate 
• 954410-12-9 methyl 3-((3S)-3-(azidomethyl)-4-{[1-(3-ethoxyphenyl)-2-(2-fluoro-4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazin-1-yl)-1-naphthoate 
• 954410-14-1 C₃₈H₃₈FN₅O₅ 
• 954410-00-5 methyl 3-[(3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-(hydroxymethyl)piperazin-1-yl]-1-naphthoate 

Relevant academic research and scientific papers

Synthesis and cycloxygenase inhibitory properties of new naphthalene-methylsulfonamido, naphthalene-methylsulfonyl and tetrahydronaphthalen-methylsulfonamido compounds

We synthesized a series of new naphthalene derivatives: naproxen- and 6-methoxy naphthalene acetic acid-like 1-5. In these compounds the carboxylic function, typical of the classical NSAIDs, was replaced by a methylsulfonamido (1, 2 and 6a-c) or methylsulfonyl (3-5) group present in some selective COX-2 inhibitors. We also synthesized compounds 7 and 8 in which the naphthalene portion was substituted by tetrahydronaphthalene ring. Some of the new compounds were assayed for their enzymatic inhibitory activity towards cycloxygenase enzymes. Compounds 4 and 6b, at a concentration of 10 μM exhibit percentage inhibition values of 65%, 50% and 29%, 87% towards COX-2 and COX-1, respectively. The substitution of carboxylic group with a mehylsulfonamido or a methylsulfonyl groups does not allow to direct the selectivity versus to cycloxygenase enzymes.

Fluorescent chemosensor for chloroalkanes

Two structurally related macrocyclic amines with naphthalene groups are shown to act as fluorescent dosimeters for reactive chloroalkanes, including the common Industrial solvent dichloromethane. The macrocyclic structures contain two NH residues which greatly accelerate N-alkylation by activating the chloride leaving group. The chemical reaction increases fluorescence Intensity by promoting excimer emission and attenuating the quenching Induced by photoinduced electron transfer (PET).

SUBSTITUTED IMIDAZOLE 4-CARBOXAMIDES AS CHOLECYSTOKININ-1 RECEPTOR MODULATORS

Certain novel substituted imidazole 4-carboxamides are ligands of the human cholecystokinin receptor and, in particular, are selective ligands of the human cholecystokinin-1 receptor (CCK-1R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of CCK-1R, such as obesity, and diabetes.

ENZYME MODULATORS AND TREATMENTS

Novel compounds and methods of using those compounds for the treatment of inflammatory conditions, hyperproliferative diseases, cancer, and diseases characterized by hypervascularization are provided. In a preferred embodiment, modulation of the activation state of p38 kinase protein ab1 kinase protein, bcr-ab1 kinase protein, braf kinase protein, VEGFR kinase protein, or PDGFR kinase protein comprises the step of contacting said kinase protein with the novel compounds.

Chemical modification of the naphthoyl 3-position of JWH-015: In search of a fluorescent probe to the cannabinoid CB2 receptor

In silico modelling was used to guide the positioning of the fluorescent dye NBD-F on the cannabinoid CB2 receptor agonist JWH-015. While the ultimate fluorescent conjugate lost extensive binding affinity to the cannabinoid CB2 receptor, affinity and efficacy studies on the naphthoyl 3-position modified precursor molecules have provided new insight into structure-activity relationships associated with this position.

(Aminoalkyl)indole isothiocyanates as potential electrophilic affinity ligands for the brain cannabinoid receptor

A series of (aminoalkyl)indole compounds, naphthalene analogs of pravadoline (1), has been shown to exhibit cannabinoid agonist activities such as antinociception in animals, inhibition of adenylate cyclase in brain membranes, and binding to the cannabinoid receptor. These pravadoline analogs were selected for the preparation of potential electrophilic affinity ligands based on the synthesis of isothiocyanate derivatives. One isothiocyanatonaphthalene derivative (8) displaced [3H]CP-55940 binding to a rat brain P2 membrane preparation with an IC50 of 690 nM, which was 10- fold less potent than the parent molecule (IC50 = 73 nM). Isothiocyanate substitution at various positions on the naphthalene moiety of the desmethyl analog 10 gave compounds that displaced [3H]CP-55940 with IC50 values between 400 and 1000 nM, compared with 46 nM for the parent compound 10. However, 6-isothiocyanato substitution on the indole ring of the desmethyl analog provided isothiocyanate 12 that displaced [3H]CP-55940 binding with an IC50 of 160 nM. After pretreatment of brain membranes with this high- affinity isothiocyanato ligand followed by washing out the ligand, the membranes were depleted of 90% of the cannabinoid receptor binding capacity. Loss of receptor binding capacity was half-maximal at 300 nM of the derivative under standard assay conditions. As a control, pretreatment with the parent compound at concentrations that were 20 times the K(d) failed to alter subsequent binding activity. This study demonstrates that an isothiocyanato (aminoalkyl)indole (12) can behave as an affinity ligand which binds irreversibly to the cannabinoid receptor in brain and which precludes subsequent binding of the cannabinoid ligand [3H]CP-55940.

ACETYLENIC FRAGMENTATION OF ACYL DERIVATIVES OF THE FISCHER BASE

Indolenium salts, which readily undergo cleavage in aqueous alkali to give a monosubstituted acetylene and 1,3,3-trimethyl-2-oxindole, are formed when acyl derivatives of the Fischer base are heated with phosphorus oxychloride.Various aryl- and hetarylacetylenes can be conveniently obtained by this method.

INDO- AND BENZINDOCYANINE DYES WITH FLUORINE-CONTAINING SUBSTITUENTS

Syntheses are reported for 2,3,3-trimethyl-3H-indoles and 1,1,2-trimethyl-1H-benzindoles with fluorine-containing substituents (CF3, SCF3, and SO2CF3) at C-5 and for carbocyanine, merocyanine, and styryl dye derivatives of these indoles.The fluorine-containing substituents studied produce a bathochromic effect in the styryl dyes, hypsochromic effect in the merocyanine dyes, and, as a rule, a hypsochromic effect in the carbocyanine dyes.