70696-57-0

Basic information

• Product Name: 4-methoxy-1-naphthoyl chloride
• Synonyms: 4-methoxy-1-naphthoyl chloride;4-Methoxy-1-naphthalenecarbonyl Chloride
• CAS NO: 70696-57-0
• Molecular Formula: C₁₂H₉ClO₂
• Molecular Weight: 221
• EINECS: -0
• Product Categories: Aromatics;Intermediates
• Mol File: 70696-57-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-methoxy-1-naphthoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-1-naphthoyl chloride(70696-57-0)
• EPA Substance Registry System: 4-methoxy-1-naphthoyl chloride(70696-57-0)

Safety Data

• Hazardous Substances Data: 70696-57-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-methoxy-1-naphthoyl chloride is used as a chemical intermediate for the preparation of isoindole derivatives, which are compounds with potential therapeutic applications in the treatment of gastrointestinal diseases. These derivatives may exhibit beneficial properties such as anti-inflammatory, analgesic, and antipyretic effects, making them valuable in the development of new medications for gastrointestinal disorders.

Upstream product

• 13041-62-8 4-methoxy-1-naphthoic acid 
• 5961-55-7 4-methoxy-1-naphthalenecarbonitrile 
• 15971-29-6 4-methoxy-1-naphthaldehyde 

Downstream Products

• 745821-84-5 4-methoxy-naphthalene-1-carboxylic acid (3-fluoro-phenyl)-amide 
• 210179-46-7 JWH-081 
• 210179-44-5 (1-butyl-1H-indol-3-yl)(4-methoxy-1-naphthalenyl)methanone 

Relevant articles and documents

Palladium-catalyzed directing group-assisted C8-triflation of naphthalenes

The transition-metal-catalyzed direct triflation of naphthyl amides and naphthyl ketones has been accomplished for the first time. Benzophenone (BP) was found to be a suitable ligand for the cross-coupling reactions. Density functional theory (DFT) calculations revealed that excessive amounts of HOTf inhibit the reductive elimination of the C-F bond to realize the unusual reductive elimination of the C-OTf bond.

Facile synthesis of lipophilic δ-amino acid conjugates from 4-alkoxy-dithionaphthoic acids

(Chemical Equation Presented) Novel 4-alkoxy-dithionaphthoic acids were prepared and shown to be valuable synthons for δ-amino acid conjugates. These dithioacids are efficiently synthesized and purified, stable to storage, and easily derivatized to facilitate thioacylation chemistry. To this end, we have demonstrated dithionaphthoic acids (6) to successfully undergo coupling with both protected and unprotected amino acids, giving rise to stable thioamide conjugates (8 and 9). Copyright Taylor & Francis Group, LLC.

ISOINDOLE DERIVATIVES USEFUL FOR TREATING PAIN, GASTROINTESTINAL DISEASES AND CANCER

Compounds of formula I or pharmaceutically acceptable salts thereof: [Chemical formula should be inserted here. Please see paper copy] I wherein X, R1, R2, R3, m and n are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

Synthesis and structure-activity relationship of a novel series of aminoalkylindoles with potential for imaging the neuronal cannabinoid receptor by positron emission tomography

A new series of CB1 ligands with high binding affinity (K i = 0.7-100 nM) and moderate lipophilicity (cLogD7.4) in the range of 2.1-4.5 has been synthesized. A structure-activity relationship study demonstrated that for the studied set of aminoalkylindoles, the molecular dipole of the ground state conformation within the series was inversely related to the affinity. The racemic ligand with highest affinity (0.7 nM), 3-(4-fluoronaphthoyl)-1-(N-methylpiperidin-2-ylmethyl)indole, was radiolabeled with 18F. This radioligand specifically labeled CB1 receptors in mouse brain and accumulated in regions of high versus low CB 1 receptor density in a ratio of 1.6. The displaceable radioactivity of one enantiomer in the brains of mice determined in a pretreatment study using the CB1 antagonist N-(piperidinyl)-5-(4-chlorophenyl)-1-(2,4- dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716) was nearly double that of the race-mate for the same determination; therefore, the active enantiomer is a candidate for PET studies in animals. A pretreatement study for the other enantiomer found no displaceable radioactivity in the same group of mice; this result suggested the enantiomer was inactive.

Protein-protein interaction antagonist screening libraries based upon 1,4-disubstituted naphthalenes and related scaffolds

The present invention relates to 1,4-disubstituted naphthalene scaffold compounds and other closely related scaffold compounds. The present invention also relates to combinatorial libraries of such compounds. In addition, the present invention relates to

THERAPEUTIC COMPOUNDS: PYRIDINE AS SCAFFOLD

Compounds of formulas I, IA, and IB or IC or pharmaceutically acceptable salts thereof: wherein A, A1, A2, A3, A4, R2, R3, R4 and n are as defined in the specifications well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

Privileged scaffolds for blocking protein-protein interactions: 1,4-Disubstituted naphthalene antagonists of transcription factor complex HOX-PBX/DNA

Structure-based-design studies, with the crystal structure of the HOXB1-PBX1/DNA transcription factor complex, were used to identify 1,4-disubstituted naphthalenes as potential antagonists. An initial library of 32 analogs was synthesized, two of which were found to be more potent than the reported activity for a 12 amino acid peptide antagonist. Antagonists were also identified of the related BRN1/DNA and BRN2/DNA transcription factor complexes indicating that a 1,4-disubsituted naphthalene may be a privileged scaffold for preparing screening libraries targeting this family of transcription factor complexes.

Behavior of naphthoyloxyl and methoxynaphthoyloxyl radicals generated from the photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones

1-Naphthoyloxyl and 2-naphthoyloxyl radicals were generated from photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones in acetonitrile. The difference in product distribution between the precursors is ascribed to the contribution of the two-bond cleavage in the peroxide decomposition in the singlet state. A series of methoxynaphthoyloxyl radicals were also generated from the corresponding (methoxynaphthoyloxy)pyridones and their behavior was compared with that of unsubstituted naphthoyloxyl radicals. The introduction of a methoxy group in the naphthalene ring stabilizes the naphthoyloxyl radicals to prevent their decarboxylation completely and reduces remarkably their reactivities in the addition to olefins and hydrogen-atom abstraction. The structure of the naphthoyloxyl radicals was discussed on the basis of their absorption spectra and MO calculations.

3-Indolyl-1-naphthylmethanes: New cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor

A series of 1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (9-11) and 2-methyl-1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (12-14) have been synthesized to investigate the hypothesis that cannabimimetic 3-(1-naphthoyl)indoles interact with the CB1 receptor by hydrogen bonding to the carbonyl group. Indoles 9-11 have significant (Ki=17-23 nM) receptor affinity, somewhat less than that of the corresponding naphthoylindoles (5, 15, 16). 2-Methyl-1-indoles 12-14 have little affinity for the CB1 receptor, in contrast to 2-methyl-3-(1-naphthoyl)indoles 17-19, which have affinities comparable to those of 5, 15, 16. A cannabimimetic indene hydrocarbon (26) was synthesized and found to have Ki=26±4 nM. Molecular modeling and receptor docking studies of naphthoylindole 16, its 2-methyl congener (19) and indolyl-1-naphthylmethanes 11 and 14, combined with the receptor affinities of these cannabimimetic indoles, strongly suggest that these cannabinoid receptor ligands bind primarily by aromatic stacking interactions in the transmembrane helix 3-4-5-6 region of the CB1 receptor.

Aminoalkylindoles: Structure - Activity Relationships of Novel Cannabinoid Mimetics

Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands.In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of 3H>Win 55212-2 (5).Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists.The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (H) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position.A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist.Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids.The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid.Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).