39181-61-8

Usage

InChI:InChI=1/C10H14N2O/c11-12-10(13)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8,11H2,(H,12,13)

Upstream product

• 10031-93-3 ethyl 4-phenylbutyrate 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 1821-12-1 4-Phenylbutyric acid 

Downstream Products

• 51716-09-7 3-[(4-phenyl-butyrylhydrazono)-methyl]-rifamycin 
• 95060-17-6 4-Phenyl-butyric acid [2-oxo-1,2-dihydro-indol-(3Z)-ylidene]-hydrazide 
• 77814-38-1 4-phenylbutyroyl azide 
• 436155-47-4 methyl N²-(4-phenylbutanoyl)carbazate 
• 866755-73-9 (2R,3R,4R,5R)-2,5-Bis-((E)-3-bromo-allyloxy)-3,4-dihydroxy-6-oxo-6-[N'-(4-phenyl-butyryl)-hydrazino]-hexanoic acid ((1S,2R)-2-hydroxy-indan-1-yl)-amide 
• 937248-17-4 C₃₄H₃₉N₅O₃ 
• 937248-73-2 C₃₄H₃₉N₅O₂ 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1007846-51-6 C₃₄H₃₉N₅O₃ 
• 1027954-30-8 C₃₈H₄₆N₆O₃ 
• 1007847-28-0 C₃₈H₄₆N₆O₄ 

Relevant academic research and scientific papers

Biological evaluation and docking studies of new carbamate, thiocarbamate, and hydrazide analogues of ACYL homoserine lactones as vibrio fischeri-quorum sensing modulators

A series of carbamate, thiocarbamate, and hydrazide analogues of acylhomoserine lactones (AHLs) were synthesized and their ability to modulate Vibrio fischeri-quorum sensing was evaluated. The compounds in the series exhibit variable side chain length and the possible presence of a diversely substituted phenyl substituent. Biological evaluation on the Vibrio fischeri quorum sensing system revealed that the ethyl substituted carbamate (1) display a weak agonistic activity whereas compounds with longer chain length or benzyl substituents display significant antagonistic activity. The most active compounds in the series were the 4-nitrobenzyl carbamate and thiocarbamate 7 and 11 which exhibited an IC50 value of about 20 μM. These activities are in the range of other reported of AHL-structurally related quorum sensing (QS) inhibitors. Docking experiments conducted on the LuxR model showed that, compared to the natural ligand OHHL, the additional heteroatom of the carbamate group induces a new hydrogen bond with Tyr70 leading to a different global hydrogen-bond network. Tyr70 is an important residue in the binding site and is strictly conserved in the LuxR family. For the 4-nitrobenzyl carbamate and thiocarbamate analogues, the docking results highlight an additional hydrogen bond between the nitro group and Lys178. For hydrazide analogues, which are deprived of any activity, docking shows that the orientation of the carbonyl group is opposite as compared with the natural ligand, leading to the absence of a H-bond between the C=O with Tyr62. This suggests that, either this later interaction, or the influence of the C=O orientation on the overall ligand conformation, are essential for the biological activity.

Synthesis of 1-(3-phenylpropyl)-4-(pyridinylmethoxy)-[1,2,4]triazolo[4,3-a] quinoxalines

Starting from 2,3-dichloroquinoxaline, a synthetic strategy for the preparation of 1-(3-phenylpropyl)-4-(pyridinylmethoxy)[1,2,4]triazolo[4,3-a]quinoxalines is described.

Exploration of diphenylalkyloxadiazoles as novel cardiac myosin activator

To explore novel cardiac myosin activator, a series of diphenylalkyl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazoles have been prepared and tested for cardiac myosin ATPase activation in vitro. In all cases, three carbon spacer between the oxadiazole core and one of the phenyl ring was considered crucial. In case of 1,3,4-oxadiazole, zero to two carbon spacer between oxadiazole core and other phenyl ring are favorable. Phenyl ring can be replaced by cyclohexyl moiety. In case of 1,2,4-oxadiazole, zero or one carbon spacer between the oxadiazole and other phenyl ring are favorable. Introduction of hydrogen bonding donor (NH) group at the 2nd position of the 1,3,4-oxadiazole enhances the activity. Substitutions on either of the phenyl rings or change of phenyl ring to other heterocycle are not tolerated for both the oxadiazoles. The prepared oxadiazoles showed selective activation for cardiac muscle over smooth and skeleton muscles.

2,3,4-Trihydroxybenzyl-hydrazide analogues as novel potent coxsackievirus B3 3C protease inhibitors

Human coxsackievirus B3 (CVB3) 3C protease plays an essential role in the viral replication of CVB3, which is a non-enveloped and positive single-stranded RNA virus belonging to Picornaviridae family, causing acute viral myocarditis mainly in children. During optimization based on SAR studies of benserazide (3), which was reported as a novel anti-CVB3 3Cpro agent from a screening of compound libraries, the 2,3,4-trihydroxybenzyl moiety of 3 was identified as a key pharmacophore for inhibitory activity against CVB3 3Cpro. Further optimization was performed by the introduction of various aryl-alkyl substituted hydrazide moieties instead of the serine moiety of 3. Among the optimized compounds, 11Q, a 4-hydroxyphenylpentanehydrazide derivative, showed the most potent inhibitory activity (IC50 Combining double low line 0.07 μM). Enzyme kinetics studies indicated that 11Q exhibited a mixed inhibitory mechanism of action. The antiviral activity against CVB3 was confirmed using the further derived analogue (14b) with more cell permeable valeryl ester group at the 2,3,4-trihydroxy moiety.

AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE

The present invention relates to the filed of pharmarcutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) amd a preparation method thereof, a pharmarcutical composition with the compounds as active components, and a use of the azole compounds and the pharmarcutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as deinfed in the specifictaion.

AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE

The present invention relates to the field of pharmaceutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) and a preparation method thereof, a pharmaceutical composition with the compounds as active components, and a use of the azole compounds and the pharmaceutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as defined in the specification.

Hydrophobic derivatization of N-linked glycans for increased ion abundance in electrospray ionization mass spectrometry

A library of neutral, hydrophobic reagents was synthesized for use as derivatizing agents in order to increase the ion abundance of N-linked glycans in electrospray ionization mass spectrometry (ESI MS). The glycans are derivatized via hydrazone formation and are shown to increase the ion abundance of a glycan standard more than 4-fold. Additionally, the data show that the systematic addition of hydrophobic surface area to the reagent increases the glycan ion abundance, a property that can be further exploited in the analysis of glycans. The results of this study will direct the future synthesis of hydrophobic reagents for glycan analysis using the correlation between hydrophobicity and theoretical non-polar surface area calculation to facilitate the development of an optimum tag for glycan derivatization. The compatibility and advantages of this method are demonstrated by cleaving and derivatizing N-linked glycans from human plasma proteins. The ESI-MS signal for the tagged glycans are shown to be significantly more abundant, and the detection of negatively charged sialylated glycans is enhanced.

Synthesis and pharmacological in vitro and in vivo evaluations of novel triazole derivatives as ligands of the ghrelin receptor. 1

A new series of growth hormone secretagogue (GHS) analogues based on the 1,2,4-triazole structure were synthesized and evaluated for their in vitro binding and their ability to stimulate intracellular calcium release to the cloned hGHS-1a ghrelin receptor expressed in LLC PK-1 cells. We have synthesized potent ligands of this receptor, some of them behaving as agonists, partial agonists, or antagonists. Some compounds among the most potent, i.e., agonist 29c (JMV2873), partial agonists including 21b (JMV2810), antagonists 19b (JMV2866) and 19c (JMV2844), were evaluated for their in vivo activity on food intake, after sc injection in rodents. Some compounds were found to stimulate food intake like hexarelin; some others were identified as potent hexarelin antagonists in this assay. Among the tested compounds, 21b was identified as an in vitro ghrelin receptor partial agonist, as well as a potent in vivo antagonist of hexarelin-stimulated food intake in rodents. Compound 21b was without effect on GH release from rat. However, in this series of compounds, it was not possible to find a clear correlation between in vitro and in vivo results.

Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone-phenol rearrangement to provide the corresponding quinolone-phenol in high yield.

A study on the influence of a silicon group on the Curtius reaction

The effect of a dimethyl(phenyl)silyl group at different positions with respect to an acyl azide moiety on the Curtius reaction has been investigated. A silyl group at the β-position enhanced the reaction rate by about three times compared to a non-silylated analog. However, a silyl group at the γ-position had only a minor influence on the reaction. A diacyl azide having a silyl group at the β-position with respect to one acyl azide group and at the γ-position with respect to the other acyl azide group has been prepared and subjected to the Curtius reaction in order to evaluate the possible synthetic potential which originates from the control exerted by the silicon group in such systems.