40130-25-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 218, 1962 DOI: 10.1021/jo01048a055

InChI:InChI=1/C8H9NO4/c1-2-13-8-5-6(9(11)12)3-4-7(8)10/h3-5,10H,2H2,1H3

Upstream product

• 4992-63-6 4-Nitro-1,2-diethoxybenzene 
• 36160-52-8 2-ethoxy-4-nitroanisole 
• 94-71-3 2-Ethoxyphenol 
• 832102-12-2 2-{[(methyloxy)methyl]oxy}-5-nitrophenol 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 

Downstream Products

• 55483-70-0 3-ethoxy-4-hydroxyaniline 
• 601488-03-3 2-acetoxy-3-(3-ethoxy-2-hydroxy-5-isopropoxycarbonylamino-phenylsulfanyl)-propionic acid ethyl ester 
• 135325-73-4 isopropyl 3-ethoxy-4-hydroxycarbanilate 

Relevant academic research and scientific papers

Synthesis and Antileishmanial Evaluation of Arylimidamide-Azole Hybrids Containing a Phenoxyalkyl Linker

Due to the limitations of existing medications, there is a critical need for new drugs to treat visceral leishmaniasis. Since arylimidamides and antifungal azoles both show oral activity in murine visceral leishmaniasis models, a molecular hybridization approach was employed where arylimidamide and azole groups were separated by phenoxyalkyl linkers in an attempt to capitalize on the favorable antileishmanial properties of both series. Among the target compounds synthesized, a greater antileishmanial potency against intracellular Leishmania donovani was observed as the linker length increased from two to eight carbons and when an imidazole ring was employed as the terminal group compared to a 1,2,4-triazole group. Compound 24c (N-(4-((8-(1H-imidazol-1-yl)octyl)oxy)-2-isopropoxyphenyl) picolinimidamide) displayed activity against L. donovani intracellular amastigotes with an IC50 value of 0.53 μM. When tested in a murine visceral leishmaniasis model, compound 24c at a dose of 75 mg/kg/day p.o. for five consecutive days resulted in a modest 33% decrease in liver parasitemia compared to the control group, indicating that further optimization of these molecules is needed. While potent hybrid compounds bearing an imidazole terminal group were also strong inhibitors of recombinant CYP51 from L. donovani, as assessed by a fluorescence-based assay, additional targets are likely to play an important role in the antileishmanial action of these compounds.

Decoquinate derivatives: A new class of potent antischistosomal agents against Schistosoma japonicum

Decoquinate (1), an old and inexpensive coccidiostat, exhibited potent antimalarial activity, however, its antischistosomal activity against Schistosoma japonicum has not yet been evaluated. Based on decoquinate, a series of decoquinate derivatives was designed, synthesized, evaluated as a new class of antischistosomal agents against S. japonicum adult worms in vitro. Among them, compound 15 killed 100% of adult S. japonicum in 72?h at the concentration of 10?μmol/L in vitro, exhibited stronger worm-killing activity than PZQ in vitro and could serve as a promising lead compound to develop new antischistosomal agents.

A intermediate [...] 2-hydroxy-5-nitrophenetol preparation method (by machine translation)

This invention has offered a kind of [...] intermediate 2-hydroxy-5-nitrophenetol preparation method, the specific method of operation: added to the reaction vessel and dichloroethane ortho-hydroxy phenetole, for 0 °C slow dropwise N 2 O 5-dichloroethane solution, adds Bi Yu 30-35 ° C reaction 1-2 hours after, adding water to the reaction solution, extracting the organic phase, the resulting organic phase is dried by anhydrous sodium sulfate, filtered, the solvent is distilled under reduced pressure to obtain the required 2-hydroxy-5-nitrophenetol. This invention adopts the N 2 O 5/C 2 H 4 Cl 2 solution for nitration reagent reaction is high in efficiency, less side reaction, no waste acid pollution, the significance of specific green the environment-friendly production, the resulting product 2-hydroxy-5-nitrophenetol purity as high as 97% or more, the yield is up to 95% or more, the preparation method of mild reaction conditions and the process is simple, easy to operate, is suitable for industrial production. (by machine translation)

NPY ANTAGONISTS, PREPARATION AND USES

The present invention concerns novel compounds, their preparation and their uses, therapeutic uses in particular. More specifically it concerns derivative compounds having at least two aromatic cycles, their preparation and their uses, in particular in the area of human or animal health. These compounds have an affinity for the biological receptors of neuropeptide Y, NPY, present in the central and peripheral nervous systems. The compounds of the invention are preferably NPY antagonists, and more particularly antagonists of sub-type NPY Y1, and can therefore be used for the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also concerns pharmaceutical compositions containing said compounds, their preparation and their uses, as well as treatment methods using said compounds.

Highly efficient catalytic nitration of phenolic compounds by nitric acid with a recoverable and reusable Zr or Hf oxychloride complex and KSF

Phenolic compounds can be nitrated with 60% nitric acid (1.2 equiv.) in the presence of catalytic amounts of a Zr or Hf oxychloride complex and montmorillonite KSF to give the corresponding nitrated products in good yields in a heterogeneous catalytic system. The co-catalyst and montmorillon ite can be easily recovered and reused in the next batch of nitration. This is a practical process for the nitration of phenolic compounds in a clean way. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Nitration of phenolic compounds by metal-modified montmorillonite KSF

The nitration of phenolic compounds with 60% nitric acid (1.2 equiv) has been carried out in the presence of metal-modified montmorillonite KSF, prepared from different metals (V, Mo, W; Sc, La, Yb, Eu, In, Bi, Ti, Zr, Hf) and KSF or nitric acid treated HKSF, as catalysts. These catalysts showed good stabilities and high catalytic activities in nitration process. In addition, these catalysts can be recovered easily and reused for many times in nitration. This process is an eco-safer and environment-benign way for clean synthesis of nitrated phenolic compounds.

Metabolism of fungicide diethofencarb in grape (Vitis vinifera L.): Definitive identification of thiolactic acid conjugated metabolites

The metabolic fate of diethofencarb (isopropyl 3,4-diethoxycarbanilate) separately labeled with 14C at the phenyl ring and 2-position of the isopropyl moiety was studied in grape (Vitis vinifera L.). The acetonitrile solution of 14C-diethofencarb at a rate of 500 g a.i. ha -1 was once applied topically to fruits or leaves at the maturity stage of fruits (PHI 35 days), and the plants were grown in the greenhouse until harvest. In the grape plants, diethofencarb was scarcely translocated to the untreated portion and was degraded more in the fruit as compared to the leaf. For the fruit, diethofencarb primary underwent O-deethylation at the 4-position of the phenyl ring to form the phenolic derivative, isopropyl 3-ethoxy-4-hydroxycarbanilate (0.9% of the total radioactive residue, TRR). This metabolite was successively transformed via conjugation with glucose at the phenolic hydroxy group (8.1-18.1% TRR) or with thiolactic acid at the 5-position of the phenyl ring (1.5-1.7% TRR). The thiolactic acid conjugate was further metabolized mainly to two different types of glucose conjugates at the 4-position of the phenyl ring (8.7-13.5% TRR) and the hydroxy group in the thiolactic acid moiety (6.4-7.3% TRR), as evidenced by 1H NMR and atmospheric pressure chemical ionization-liquid chromatography-mass spectrometry together with cochromatographies with synthetic standards.