40926-77-0

Usage

Uses

Used in Pharmaceutical Industry:
(2-Naphthyloxy)acetyl chloride is used as a reagent for the discovery of indoline-2-carboxamide derivatives, which are a new class of brain-penetrant inhibitors of Trypanosoma brucei. This parasitic infection is the causative agent of African trypanosomiasis, also known as sleeping sickness. The development of new inhibitors is crucial for the treatment of this disease, as it can be fatal if left untreated.
Used in Chemical Synthesis:
(2-Naphthyloxy)acetyl chloride is also used in the preparation and antibacterial activity of N-(phenylquinazolinonyl) aryl-amides. These compounds are synthesized through the amidation of amino(phenyl)quinazolone with aroyl chlorides, including (2-naphthyloxy)acetyl chloride. The resulting N-(phenylquinazolinonyl) aryl-amides exhibit antibacterial properties, making them potential candidates for the development of new antibiotics to combat drug-resistant bacterial infections.

Upstream product

• 120-23-0 (2-naphthoyl)oxyacetic acid 
• 6036-14-2 ethyl (naphthalen-2-yloxy)acetate 
• 135-19-3 β-naphthol 

Downstream Products

• 102318-57-0 [2]naphthyloxyacetic acid-[(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethylamide] 
• 78162-22-8 [2]naphthyloxy-acetic acid anilide 
• 67141-68-8 N-sec-butyl-2-(naphthalen-2-yloxy)acetamide 
• 67141-73-5 N,N-Dibutyl-2-(naphthalen-2-yloxy)-acetamide 
• 136801-31-5 2-(Naphthalen-2-yloxy)-1-phenothiazin-10-yl-ethanone 
• 10441-31-3 2-[2-(Naphthalen-2-yloxy)-acetylamino]-3-phenyl-propionic acid 
• 19997-42-3 1,2-dihydronaphtho[2,1-b]furan-1-one 
• 349644-45-7 2-[2-(naphthalen-2-yloxy)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 36304-47-9 1-(2-naphthyloxyacetyl)hydrazine 
• 300666-43-7 (+/-)-2,2'-bis(diphenylphosphino)-3,3'-binaphtho[2,1-b]furan 
• 300666-45-9 (S)-2,2'-bis(diphenylphosphinyl)-3,3'-binaphtho[2,1-b]furan 

Relevant academic research and scientific papers

Synthesis and biological evaluation of aryloxyacetamide derivatives as neuroprotective agents

A series of new aryloxyacetamide derivatives 10a-s and 14a-m are designed and synthesized. Their protective activities against the glutamate-induced cell death were investigated in differentiated rat pheochromocytoma cells (PC12 cells). Most compounds exhibited neuroprotective effects, especially for 10m, 10r, 14b and 14c, which showed potential protection of PC12 cells at three doses (0.1, 1.0, 10 μM). MTT assay, Hoechst 33342/PI double staining, and high content screening (HCS) revealed that pretreatment of the cells with 10m, 10r, 14b and 14c has significantly decreased the extent of cell apoptosis in a dose-dependent manner. The results of western blot analysis demonstrated these compounds suppressed apoptosis of glutamate-induced PC12 cells via caspase-3 pathway. These compounds can be lead compounds for further discovery of neuroprotective agents for treating cerebral ischemic stroke. Basic structure-activity relationships are also presented.

Synthesis, biological evaluation, and structure-activity relationships of potent noncovalent and nonpeptidic cruzain inhibitors as anti-Trypanosoma cruzi agents

The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (Ki = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, Ki = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.

PYRAZOLE DERIVATIVES, PREPARATION METHOD THEREOF, AND COMPOSITION FOR PREVENTION AND TREATMENT OF OSTEOPOROSIS CONTAINING SAME

The present invention provides pyrazole derivative compounds and pharmaceutically acceptable salts thereof. The compounds of the present invention have an excellent effect of preventing and treating osteoporosis.

DERIVATIVES OF BENZOTHIAZINES, PREPARATION THEREOF AND APPLICATION THEREOF AS DRUGS

The object of the present invention is benzothiazine derivatives having the capability of inhibiting 11β-HSD1 not only at an enzymatic level but also at a cell level. The compounds of the present invention are of general formula (I). Wherein notably R1 represents a hydrogen or OR1 represents an ester or an ether. R2 represents a naphthyl or a 1, 2, 3, 4-tetrahydro-naphthalene or a biphenyl or phenyl pyridine or a substituted phenyl. R3 represents a methyl or ethyl; R4 and R'4 represent a hydrogen.

Synthesis and biological evaluation of some substituted amino thiazole derivatives

Condensation of acetophenone with thiourea in presence of halogen (Iodine) gives 2-amino-4-phenylthiazole (I). 2-Amino-4-phenyl-5-phenylazothizole (II) was prepared by coupling of phenyldiazonium chloride with 2-amino-4-phenylthiazole (I). A series of amide can be synthesized by treatment of appropriate substituted acid chlorides (III) with compound (II) using pyridine as solvent. All the synthesized compounds are characterized by the combination of elemental analysis and standard spectroscopic method. They are screened for anti-bacterial activity against Escherichia coli and Staphylococcus aureus as well as screened for antifungal activity against Aspergillus niger and Apergillus oryzae by cup plate method at 1μg/mL concentration in DMF. All the synthesized compounds showed moderate to good microbial activity.

Synthesis, resolution, and application of 2,2′-bis(diphenylphosphino) -3,3′-binaphtho[b]furan (BINAPFu)

(±)-2,2′-Bis(diphenylphosphino)-3,3′-binaphtho[2,1-b] furan (BINAPFu) was synthesized from 2-naphthoxyacetic acid in a five-step sequence in 62% overall yield. A variety of reported resolution procedures for biaryl bisphosphines did not work with (±)-BINAPFu; thus, a new resolution method was developed, involving the Staudinger reaction of the aforementioned racemate of BINAPFu with an enantiopure camphor sulfonyl azide derivative. The resulting diastereomeric phosphinimines were separated by flash chromatography. Subsequent hydrolysis to the corresponding bis-phosphine oxide and trichlorosilane reduction provided enantiopure BINAPFu. The absolute stereochemical configuration of BINAPFu was established by X-ray crystallography. BINAPFu was compared with commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP) in Pd(0)-catalyzed intermolecular Heck reactions. Investigation of the Heck arylation of 2,3-dihydrofuran showed BINAPFu to be more efficacious than BINAP in dioxane at 30°C. A variety of phosphorus selenides were prepared, and the 1JP-Se coupling constants measured, to obtain a comparative scale of parent phosphine basicity. The phosphorus atoms in BINAPFu were found to be electron deficient when compared with BINAP but slightly more electron rich than trifurylphosphine.

3-(Arylacetylamino)-N-methylbenzamides: A novel class of selective anti-Helicobacter pylori agents

After chemical modification preceded by the random screening of our chemical library, a novel class of selective anti-Helicobacter pylori agents was generated. Consequently, the 3-(arylacetylamino)-N-methylbenzamides, which were quite easy to prepare, showed potent inhibitory activity against Helicobacter pylori but exhibited no inhibitory activity against other sorts of bacteria and fungi, e.g., Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa, Bacteroides fragilis, and Candida albicans. These compounds showed potent anti-H. pylori activity under acidic conditions, whereas amoxicillin and clarithromycin decreased activity. The 3-(3-arylpropionylamino)-N-methylbenzamides, 3-(aryloxyacetylamino)-N-methylbenzamides, and (3-methylcarbamoylphenyl)carbamic acid 1-arylmethyl esters also exhibited potent anti-H. pylori activity. Finally, we selected 7n (BAS-118) as a candidate compound for further evaluation.

Design, synthesis and antihistaminic (H1) activity of some condensed 3- aminopyrimidin-4(3H)-ones

A novel series of condensed 3-amino-2-(substituted)methylpyrimidin- 4(3H)-ones is reported with potential H1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA2 value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect the antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling, studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Synthesis of lariat ethers with pendent N,N-dialkyl oxyacetamide groups

Synthetic routes to thirty crown ether compounds with pendent N,N-dialkylamide groups are reported. The new lariat ethers are based on sym-(R)dibenzo-13-crown-4-oxyacetamide, sym-(R)dibenzo-14-crown-4-oxyacetamide and sym-(R)dibenzo-16-crown-5-oxyacetamide, in which R = H or alkyl, and sym-(propyl)dicyclohexano-16-crown-5-oxacetamide. Two acyclic polyether analogues with pendent N,N-dialkylamide groups are also prepared.

Bicyclic N-hydroxyurea inhibitors of 5-lipoxygenase: Pharmacodynamic, pharmacokinetic, and in vitro metabolic studies characterizing N-hydroxy-N-(2,3-dihydro-6-(phenylmethoxy)-3-benzofuranyl)urea

A series of N-hydroxyurea derivatives have been prepared and examined as inhibitors of 5-lipoxygenase. Oral activity was established by examining the inhibition of LTB4 biosynthesis in an ex vivo assay in the mouse. The pharmacodynamic performance in the mouse of selected compounds was assessed using an ex vivo LTB4 assay and an adoptive peritoneal anaphylaxis assay at extended pretreat times. Compounds with an extended duration of action were reexamined as the individual enantiomers in the ex vivo assay, and the (S) enantiomer of N-hydroxy-N-[2,3-dihydro-6-(phenylmethoxy)-3-benzofuranyl]urea, (+)-1a (SB 202235), was selected as the compound with the best overall profile. Higher plasma concentrations and longer plasma half-lives were found for (+)-1a relative to its enantiomer in the mouse, monkey, and dog. In vitro metabolic studies in mouse liver microsomes established enantiospecific glucuronidation as a likely mechanism for the observed differences between the enantiomers of 1a. Enantioselective glucuronidation favoring (-)-1a was also found in human liver microsomes.