5121-00-6

Usage

Uses

Used in Pharmaceutical Industry:
2-(1-NAPHTHYL)ETHANOYL CHLORIDE is used as a synthetic reagent for the introduction of the acyl group into organic compounds, facilitating the synthesis of various pharmaceutical compounds. Its ability to acylate compounds makes it a valuable tool in the development of new drugs and medicinal agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(1-NAPHTHYL)ETHANOYL CHLORIDE is employed as a key intermediate in the synthesis of agricultural compounds. Its reactivity in introducing acyl groups aids in the creation of effective agrochemicals designed to protect crops and enhance agricultural productivity.
The versatility of 2-(1-NAPHTHYL)ETHANOYL CHLORIDE in organic synthesis underscores its importance across different industries, where its unique properties contribute to the advancement of chemical research and product development.

InChI:InChI=1/C12H9ClO/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2

Upstream product

• 61-31-4 sodium salt of 1-naphthylacetic acid 
• 86-87-3 naphth-1-yl acetic acid 
• 4732-69-8 Chloro-oxo-acetic acid 
• 91-20-3 naphthalene 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 76580-08-0 1-(4-methoxyphenyl)-2-(naphthalen-1-yl)ethan-1-one 
• 2235-15-6 1(2H)-acenaphthylenone 
• 102613-45-6 [1]naphthylacetyl-urea 
• 6277-60-7 Naphthyl-acetylglycin 
• 140709-06-4 N,N-diisopropyl-2-(naphthalen-1-yl)acetamide 
• 102626-31-3 3-naphthylacetyloxy-2-cyclohexenone 
• 31283-78-0 1-phenyl-3-(1-naphthyl)-2-propanone 
• 166588-80-3 1-((4R,7S)-7-Isopropyl-4-methyl-3-phenyl-4,5,6,7-tetrahydro-indazol-2-yl)-2-naphthalen-1-yl-ethanone 
• 548772-87-8 (1S,2S)-2-(1-naphthylacetylamino)-1-phenyl-propane-1,3-diol 
• 676565-99-4 N-propyl-N-(2-phenylethyl)-2-(1-naphthyl)acetamide 

Relevant academic research and scientific papers

IDENTIFICATION OF NAA-L-ASPARTATE AMIDE AS THE MAJOR METABOLITE SYNTHESIZED BY TOBACCO MESOPHYLL PROTOPLASTS INCUBATED IN THE PRESENCE OF THE AUXIN ANALOGUE NAA

A major metabolite of naphthalene 1-acetic acid (NAA) is rapidly accumulated by tobacco mesophyll protoplasts induced to divide by this growth regulator.A comparison of the natural product with various chemically synthesized NAA-amino acid conjugates was performed.Themetabolite was identified as NAA-aspartate amide by negative CIMS.The biological activity of NAA-aspartate on protoplasts was further studied.The significance of the accumulation of this metabolite in dividing protoplasts is descussed.Key words: Nicotiana tabacum; Solanaceae; protoplast; NAA; auxin-amino acid; conjugates; isolation; identification.

Peri-Dimethylamino substituent effects on proton transfer at carbon in α-naphthylacetate esters: A model for mandelate racemase

The rate constants for exchange of hydrogen for deuterium at the α-CH2 positions of 8-(N,N-dimethylaminonaphthalen-1-yl)acetic acid tert-butyl ester 1 and naphthalen-1-ylacetic acid tert-butyl ester 2 have been determined in potassium deuteroxide solutions in 1:1 D2O:CD 3CN, in order to quantify the effect of the neighbouring peri-dimethylamino substituent on α-deprotonation. Intramolecular general base catalysis by the (weakly basic) neighbouring group was not detected. Second-order rate constants, kDO, for the deuterium exchange reactions of esters 1 and 2 have been determined as 1.35 × 10-4 M-1 s-1 and 3.95 × 10-3 M-1 s-1, respectively. The unexpected 29-fold decrease in the k DO value upon the introduction of a peri-dimethylamino group is attributed to an unfavourable steric and/or electronic substituent effect on intermolecular deprotonation by deuteroxide ion. From the experimental k DO values, carbon acid pKa values of 26.8 and 23.1 have been calculated for esters 1 and 2.

L-Amino acid derived pyridinium-based chiral compounds and their efficacy in chiral recognition of lactate

A series of pyridinium-based chiral compounds 1-6 have been designed and synthesized. l-Amino acids have been used as the chiral source in the molecules. Among the chiral compounds, an l-valine derived compound 1 was found to exhibit enantioselective recognition of d-lactate in fluorescence. Structural tuning of this derivative, either by replacing l-valine with l-alanine or l-phenylglycine or by reducing the number of chiral centres around the binding site, does not result in any significant change in enantioselectivity in the recognition process. Change of the urea site to amide introduces compound 6 that displays good enantiodiscrimination for lactate (enantiomeric fluorescence difference ratio ef = 28.33 for d-lactate), even better than that of the l-valine derived compound 1 and of other reported structures in the literature.

A ratiometric luminescent sensing of Ag+ ion via in situ formation of coordination polymers

A ratiometric luminescent sensing of Ag+ ion is developed via the Ag(i)-NCys coordination polymeric luminophore in situ formed in aqueous solution upon mixing Ag+ ion with the designed fluorescent thiol ligand NCys.

Synthesis, characterization and slow release properties of O-naphthylacetyl chitosan

O-naphthylacetyl chitosan (NA-chitosan) was first prepared via protecting the amino groups with phthalic anhydride, followed by reaction with 1-naphthylacetyl chloride. The intermediates were hydrolyzed with anhydrous hydrazine to obtain final product. The derivatives of each step were characterized with Fourier transform infrared spectroscopy (FT-IR) and 13C solid state nuclear magnetic resonance (NMR). Results showed NA-chitosan had both naphthylacetyl and amino groups in the main chain of the polysaccharide. Elemental analysis showed that the substitution degree of hydroxyl was 0.4. Thermogravimetric analysis (TGA, DTG) of NA-chitosan was observed with much lower decomposition peak at 283°C than that of chitosan at 300°C. The release of 1-naphthylacetic acid was dependent on both pH values and the medium temperature, and at pH 12.0, 60°C the release period could last for 55 days.

Pyridinum-based flexible tripodal cleft:A case of fluorescence sensing of ATP and dihydrogenphosphate under different conditions and cell imaging

Pyridinium-based chemosensor 1 built on tris(aminomethyl)amine (tren) has been designed, synthesized and established as a chemosensor for ATP over ADP, AMP and a series of other anions in aqueous CH3CN at pH 6.5. Compound 1 exhibits a significant change in emission upon complexation of ATP. In CH3CN, the sensor selectively binds H2PO4- and forms an excimer with significant intensity. Furthermore, the intracellular ATP detection using 1 was possible through fluorescent confocal imaging.

Synthesis and characterization of 3-O-esters of N-acetyl-D-glucosamine derivatives as organogelators

Carbohydrate derived low molecular weight organogelators are interesting compounds with many potential applications. Selective functionalization of the different hydroxyl substituents on d-glucose and d-glucosamine resulted in small molecular gelators. Previously we have found that the C-2 acylated derivatives including esters and carbamates of 4,6-O-benzylidene protected glucose and glucosamine derivatives have shown remarkable applications as molecular gelators. In this research, in order to probe the structural influence of sugar derivatives on molecular self-assembly, we introduced acylation functional groups to the 3-hydroxyl group of 4,6-O-benzylidene acetal protected N-acetyl glucosamine derivatives. A library of fourteen ester derivatives was synthesized and characterized. The ester derivatives typically formed gels in pump oil and aqueous mixtures of dimethyl sulfoxide or ethanol. The resulting gels were characterized using optical microscopy, and rheology, etc. All alkyl ester derivatives were gelators for pump oil. A short chain ester derivative was able to form gels in a few different oils and the corresponding oil water mixtures phase selectively. The compound was also used to trap naproxen sodium and formed a stable co-gel. The controlled release of the drug from the gel to the aqueous phase was analyzed using UV-vis spectroscopy. These results show that the functionalization at the 3-OH position of the N-acetyl glucosamine derivative is a feasible strategy in designing new classes of organogelators.

Annelated Pyridine Bases for the Selective Acylation of 1,2-Diols

A set of 24 annelated derivatives of 4-diaminopyridine (DMAP) has been synthesized and tested with respect to its catalytic potential in the regioselective acylation of 1,2-diol substrates. The Lewis basicities of the catalysts as quantified through quantum chemical calculations vary due to inductive substituent effects and intramolecular stacking interactions between side chain π-systems and the pyridinium core ring system. The primary over secondary hydroxyl group selectivities in catalytic acylations of 1,2-diol substrates depend on the size and the steric demand of the Lewis base and the anhydride reagent.

Novel Pyridine-Based Hydroxamates and 2′-Aminoanilides as Histone Deacetylase Inhibitors: Biochemical Profile and Anticancer Activity

Starting from the N-hydroxy-3-(4-(2-phenylbutanoyl)amino)phenyl)acrylamide (5 b) previously described by us as a HDAC inhibitor, we prepared four aza-analogues, 6–8, 9 b, as regioisomers containing the pyridine nucleus. Preliminary screening against mHDAC1 highlighted the N-hydroxy-5-(2-(2-phenylbutanoyl)amino)pyridyl)acrylamide (9 b) as the most potent inhibitor. Thus, we further developed both pyridylacrylic- and nicotinic-based hydroxamates (9 a, 9 c–f, and 11 a–f) and 2′-aminoanilides (10 a–f and 12 a–f), related to 9 b, to be tested against HDACs. Among them, the nicotinic hydroxamate 11 d displayed sub-nanomolar potency (IC50: 0.5 nM) and selectivity up to 34 000 times that of HDAC4 and from 100 to 1300 times that of all the other tested HDAC isoforms. The 2′-aminoanilides were class I-selective HDAC inhibitors, generally more potent against HDAC3, with the nicotinic anilide 12 d being the most effective (IC50HDAC3=0.113 μM). When tested in U937 leukemia cells, the hydroxamates 9 e, 11 c, and 11 d blocked over 80 % of cells in G2/M phase, whereas the anilides did not alter cell-cycle progress. In the same cell line, the hydroxamate 11 c and the anilide 10 b induced about 30 % apoptosis, and the anilide 12 c displayed about 40 % cytodifferentiation. Finally, the most potent compounds in leukemia cells 9 b, 11 c, 10 b, 10 e, and 12 c were also tested in K562, HCT116, and A549 cancer cells, displaying antiproliferative IC50 values at single-digit to sub-micromolar level.

N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesizecis-enamides through vinyl benziodoxolones

The stereoselective synthesis ofcis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) fromO-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated variousO-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuteratedcis-β-N-MeO-amide-VBXs were also synthesized using deuterium oxide as the deuterium source. Valine-derivedcis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derivedcis-enamides without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.