51439-58-8

Usage

InChI:InChI=1/C12H9ClO2/c1-15-10-7-6-8-4-2-3-5-9(8)11(10)12(13)14/h2-7H,1H3

Upstream product

• 883-21-6 1-methoxy-2-naphthoic acid 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 13343-92-5 methyl ester of 2-methoxy-1-naphthalenecarboxylic acid 
• 947-62-6 2-methoxy-1-naphthoic acid 

Downstream Products

• 106542-96-5 phenyl 2-methoxy-1-naphthoate 
• 64506-84-9 β-{4-[2-(2-methoxy-naphthalene-1-carboxamido)-ethyl]-phenyl}-propionic acid 
• 824960-76-1 (2-methoxy-1-naphthalenyl)(1-pentyl-1H-indol-3-yl)methanone 
• 818375-08-5 2-methoxy-1-naphthyl (2-acetamido-4,6-dimethoxy)phenyl ketone 
• 610794-07-5 2-methoxy-naphthalene-1-carboxylic acid benzyl-indan-2-yl-amide 
• 947-62-6 2-methoxy-1-naphthoic acid 
• 137869-22-8 2-phenyl-1-naphthaldehyde 
• 137869-15-9 2-(2-phenyl-1-naphthyl)oxazoline 
• 137869-18-2 2-<2-(O-methylephedrinyl)-1-naphthyl>oxazoline 
• 113056-73-8 2-p-tolyl-[1]naphthoic acid phenyl ester 
• 102595-97-1 2-phenyl-[1]naphthoic acid phenyl ester 
• 113056-97-6 2-o-tolyl-[1]naphthoic acid phenyl ester 
• 102664-91-5 2-benzyl-[1]naphthoic acid phenyl ester 
• 1415046-41-1 2-methoxy-6-(4-methoxyphenyl)-N,N-dimethyl-1-naphthamide 

Relevant academic research and scientific papers

Diastereoselective photocycloaddition using memory effect of molecular chirality controlled by crystallization

Naphthamides derived from L-proline, which exist as a mixture of several diastereomers in solution, converged to single diastereomer by crystallization, and the conformational transformation was controlled after the crystals were dissolved in the solvent at low temperature, where the frozen conformation was retained long enough for subsequent asymmetric reaction. The Royal Society of Chemistry.

An asymmetric SNAr reaction using the molecular chirality in a crystal

An asymmetric SNAr reaction was performed by using molecular chirality generated and amplified by the spontaneous crystallization of achiral naphthamides; the chirality was retained in a cold solution, caused by slow racemization, and was transferred to stable axially chiral materials with high enantiomeric excesses. The Royal Society of Chemistry.

Palladium-catalyzed C–P bond activation of aroyl phosphine oxides without the adjacent “anchoring atom”

A novel palladium-catalyzed decarbonylation of aroyl phosphine oxides to prepare phosphine oxides from carboxylic acids is developed. Without the adjacent “anchoring atom”, the challenging C–P bond activation is achieved in high selectivity. The disclosure of this reaction provides a new example of C–P bond activation and helps to extend the understanding of the property of C–P bond.

Beyond Directed ortho Metalation: Ruthenium-Catalyzed Amide-Directed CAr-OMe Activation/Cross-Coupling Reaction of Naphthamides with Aryl Boronates

A new and general synthetic methodology for the construction of biaryl, heterobiaryl, and polyaryl molecules by the ruthenium-catalyzed cross-coupling of ortho-methoxy naphthamides with aryl boroneopentylates is described. The isomeric 1-MeO-2-naphthamides and 2-MeO-1-naphthamides furnish an expansive series of arylated naphthamides in excellent yields. Competition experiments showed the higher reactivity of 1-MeO-2-naphthamide over 2-MeO-benzamide. Orthogonality between the C-O activation/cross-coupling and the Suzuki-Miyaura reactions was established. The method provides naphthalenes which are difficult to prepare by directed ortho metalation.

Synthesis, antitumor activity, and mechanism of action of benzo[a]pyrano[3,2-h]acridin-7-one analogues of acronycine

Twenty-two derivatives belonging to the cis-1,2-diacyloxy-6-methoxy-3,3,14- trimethyl-1,2,3,14-tetrahydro-7H-benzo[a]pyrano[3,2-h]acridin-7-one series were synthesized in nine steps starting from 3,5-dimethoxy-acetanilide (5) and 2-methoxy-1-naphthalenecarboxylic acid (7). Most of them exhibited submicromolar cytotoxicity when tested against murine leukemia (L1210) and human epidermoid carcinoma (KB-3-1) cell lines. The cytotoxic activity correlated strongly with the ability of the compounds to form covalent adducts with purified DNA. Among the most active compounds, 25, with IC50 values of 0.7 and 0.15 μM against L1210 and KB-3-1, respectively, was selected for evaluation in vivo against Colon 38 adenocarcinoma implanted in mice. This compound was active at 3 mg/kg iv (day 12 and 24) with 3/7 tumor free mice by day 80.

Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: Steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists

The synthesis and pharmacology of 47 1-alkyl-3-(1-naphthoyl)indoles (R = C3H7 and C5H11, R′ = H and CH3) is described. Naphthoyl substituents include 4- and 7-alkyl groups, plus 2, 4, 6, and 7-methoxy groups. Three of these compounds are highly selective CB2 receptor agonists. In an effort to improve indole-based CB2 cannabinoid receptor ligands and also to develop SAR for both the CB1 and CB2 receptors, 47 indole derivatives were prepared and their CB1 and CB2 receptor affinities were determined. The indole derivatives include 1-propyl- and 1-pentyl-3-(1- naphthoyl)indoles both with and without a 2-methyl substituent. Naphthoyl substituents include 4- and 7-alkyl groups as well as 2-, 4-, 6-, 7-methoxy and 4-ethoxy groups. The effects of these substituents on receptor affinities are discussed and structure-activity relationships are presented. In the course of this work three new highly selective CB2 receptor agonists were identified, 1-propyl-3-(4-methyl-1-naphthoylindole (JWH-120), 1-propyl-2-methyl-3-(6-methoxy-1-naphthoylindole (JWH-151), and 1-pentyl-3-(2-methoxy-1-naphthoylindole (JWH-267). GTPγS assays indicated that JWH-151 is a full agonist at CB2, while JWH-120 and JWH-267 are partial agonists. Molecular modeling and receptor docking studies were carried out on a set of 3-(4-propyl-1-naphthoyl)indoles, a set of 3-(6-methoxy-1- naphthoyl)indoles and the pair of N-pentyl-3-(2-methoxy-1-naphthoyl)indoles. Docking studies indicated that the CB1 receptor affinities of these compounds were consistent with their aromatic stacking interactions in the aromatic microdomain of the CB1 receptor.

Benzo[a]pyrano[3,2-h]acridin-7-one compounds

A compound selected from those of formula (I): 1 wherein: X and Y represent a group selected from hydrogen, halogen, hydroxy, alkoxy, nitro, cyano, alkyl, trihaloalkyl and NRaRb, wherein Ra and Rb are as defined in the description R1 represents hydrogen or alkyl R2 represents a group selected from hydrogen, alkyl, —OR″a, —NR′aR′b, -Ta-O″a, —N″a-Ta-NR′aR′b, —N″a—C(O)-TaH, —O—C(O) TaH, Ta-NR′aR′b, —NR″a-Ta-OR″a, —NR″a-Ta-CO2R″a and —N″a—C(O)-Ta-NR′aR′b, wherein R′a, R″a, R′b and Ta are as defined in the description R3 and R4 represent hydrogen or alkyl A represents a group of formula —CH(R5)CH(R6), —CH=C(R7)—, —C(R7)=CH—, —C(O)CH(R8) or —CH(R8)—C(O), wherein R5, R6, R7 and R8 are as defined in the description its isomers, N-oxides, and addition salts thereof with a pharmaceutically acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.

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.

SUBSTITUTED BIARYL AMIDES AS C5A RECEPTOR MODULATORS

Substituted biaryl amides of Formula I are provided. Such compounds are ligands that may be used to modulate C5a receptor activity in vivo or in vitro, and are particularly useful in the treatment of conditions associated with pathological C5a receptor activation in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for using them to treat such disorders are provided, as are methods for using such ligands for receptor localization studies.