69826-63-7

Usage

InChI:InChI=1/C13H11NO3/c15-12(16)8-14-13(17)11-6-5-9-3-1-2-4-10(9)7-11/h1-7H,8H2,(H,14,17)(H,15,16)/p-1

Upstream product

• 56-40-6 glycine 
• 2243-83-6 2-naphthaloyl chloride 
• 93-09-4 naphthalene-2-carboxylate 
• 56374-47-1 2,5-dioxopyrrolidin-1-yl 2-naphthoate 

Downstream Products

• 331957-14-3 2-(naphthalen-2-yl)-4-(thiophen-2-ylmethylene)oxazol-5(4H)-one 

Relevant academic research and scientific papers

Synthesis, biological evaluation and in silico investigation of novel functionalized imidazole-based KDM6 inhibitors

Epigenetic markers of the cellular genome are major controllers of the transcriptional level of various genes in physiological and pathological states. These markers are written and erased by epigenetic factors which have been recently studied as potentia

Novel naphthylamide derivatives as dual-target antifungal inhibitors: Design, synthesis and biological evaluation

Fungal infections have become a serious medical problem due to the high infection rate and the frequent emergence of drug resistance. Squalene epoxidase (SE) and 14α-demethylase (CYP51) are considered as the important antifungal targets, they can show the synergistic effect on antifungal therapy. In the study, a series of active fragments were screened through the method of De Novo Link, and these active fragments with the higher Ludi_Scores were selected, which can show the obvious binding ability with the dual targets (SE, CYP51). Subsequently, three series of target compounds with naphthyl amide scaffolds were constructed by connecting these core fragments, and their structures were synthesized. Most of compounds showed the antifungal activity in the treatment of pathogenic fungi. It was worth noting that compounds 10b-5 and 17a-2 with the excellent broad-spectrum antifungal properties also exhibited the obvious antifungal effects against drug-resistant fungi. Preliminary mechanism study has proved these target compounds can block the biosynthesis of ergosterol by inhibiting the activity of dual targets (SE, CYP51). Furthermore, target compounds 10–5 and 17a-2 with low toxicity side effects also demonstrated the excellent pharmacological effects in vivo. The molecular docking and ADMET prediction were performed, which can guide the optimization of subsequent lead compounds.

Amide pyridine derivative and application thereof

The invention belongs to the technical field of medicine and relates to an amide pyridine derivative which is shown as a general formula I. The invention further relates to stereoisomer and pharmaceutically-acceptable salt, hydrate, solvate or prodrug of the amide pyridine derivative. The definitions of substituent groups of Ar, M, R and Py are given out in an instruction book. The invention further relates to a method for preparing the compound shown in the general formula I, pharmaceutical composition containing the compound and application of the compound and the pharmaceutical compositionin preparing medicine for treating and preventing superficial-layer fungal diseases and deep-layer fungal diseases.

Design, synthesis and biological evaluation of amide-pyridine derivatives as novel dual-target (SE, CYP51)antifungal inhibitors

Based on the analysis of the squalene cyclooxygenase (SE)and 14α-demethylase (CYP51)inhibitors pharmacophore feature and the dual-target active sites, a series of compounds with amide-pyridine scaffolds have been designed and synthesized to treat the increasing incidence of drug-resistant fungal infections. In vitro evaluation showed that these compounds have a certain degree of antifungal activity. The most potent compounds 11a, 11b with MIC values in the range of 0.125–2 μg/ml had a broad-spectrum antifungal activity and exhibited excellent inhibitory activity against drug-resistant pathogenic fungi. Preliminary mechanism studies revealed that the compound 11b might play an antifungal role by inhibiting the activity of SE and CYP51. Notably compounds did not show the genotoxicity through plasmid binding assay. Finally, this study of molecular docking, ADME/T prediction and the construction of 3D QSAR model were performed. These results can point out the direction for further optimization of the lead compound.

Detecting a peroxide-based explosive via molecular gelation

A convenient and portable triacetone triperoxide (TATP) sensor was developed utilizing a thiol-to-disulfide oxidation to trigger a solution-to-gel phase transition. Using this method, TATP can be detected visually without any instrumentation.

Synthesis and photochemistry of pH-sensitive GFP chromophore analogs

GFP chromophore analogs (7a-e, 8, and 10a,b) containing 2-thienyl-, 5-methyl-2-furyl-, 2-pyrryl, and 6-methyl-2-pyridyl-groups were synthesized and their fluorescence spectra recorded in the pH range 1-7. NMR studies showed that protonation of 8 (2-thieny

Conjugates of naphthalene and dipeptides produce molecular hydrogelators with high efficiency of hydrogelation and superhelical nanofibers

Here we report a new class of molecular hydrogelators based on the conjugates of dipeptide and (naphthalen-2-yloxy)acetic acid. They form hydrogels efficiently - the lowest concentration for them to gel water is 0.07 wt%. Two hydrogelators show the ability to form helical nanofibers within the hydrogels, and the chirality of the hydrogelators apparently dictates the handedness of the nanofibers - d-peptide and l-peptide afford left-handed and right-handed self-assembled nanofibers in the hydrogels, respectively. Moreover, MTT assay of the viability of cells indicates that these molecular hydrogelators are biocompatible. The Royal Society of Chemistry 2007.

PROCESS FOR CONVERSION OF PHENOLS TO CARBOXAMIDES VIA THE SUCCINIMIDE ESTERS

A process for converting an aryl triflate, heteroaryl triflate, aryl halide or heteroaryl halide to an N-hydroxysuccinimido este is disclosed. The process involves reacting the triflate or halide with carbon monoxide and N-hydroxysuccinimide in a solvent in the presence of a palladium catalyst and a base.

Relative Structure-Inhibition Analyses of the N-Benzoyl and N-(Phenylsulfonyl) Amino Acid Aldose Reductase Inhibitors

A number of N-benzoyl amino acids were synthesized and tested to compare structure-inhibition relationships with the isosteric N-(phenylsulfonyl) amino acid (PS-amino acid) aldose reductase inhibitors.Inhibition analyses with these series reveals that their kinetic mechanisms of inhibition are similar, but that significant differences in structure-inhibition relationships exist.For example, while the PS-alanines and PS-2-phenylglycines produce enantioselective inhibition (S > R), no consistent pattern of enantioselectivity is observed with the isosteric N-benzoylalanines and 2-phenylglycines.Also, N-methyl and N-phenyl substitution in the PS-amino acid series does not substantially alter inhibitory activity, while similar substitutions in the N-benzoyl series (particularly N-phenyl) results in a significant increase in inhibitory activity.Proton NMR analysis of the N-benzoylsarcosines reveals that these compounds exist as a mixture of rotamers in solutions including the enzyme assay buffer and that the preferred conformer is one in which the carboxymethyl moiety is trans to the aromatic ring.Similar analyses with the N-benzoyl-N-phenylglycines demonstrate that these derivatives exist exclusively in the trans rotameric conformation in solution.No such N-substituent effects on conformation were observed in the PS-amino acid series.These results suggest that the differences in structure-inhibition trends between these structurally related series may result from the effect of substituents on preferred conformation.

Synthesis and in Vitro Aldolase Reductase Inhibitory Activity of Compounds Containing an N-Acylglycine Moiety

A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldolase reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid.Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldolase reductase obtained from rat lens, producing 50percent inhibition only at concentrations exceeding 100 μM.Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines.While this derivatives are more potent than compounds of series 6 (IC 50s of 6-80 μM), they are less active than the corresponding 2-oxoquinolines.Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids.These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC 50s of 0.1-10 μM).Of the rigid analogues of 8, the most potent derivative is benzoxindol (12) with an IC 50 of 0.67 μM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.