49678-09-3

Usage

InChI:InChI=1/C11H9NO3/c13-9-3-1-2-4-10-5-7-11(8-6-10)12(14)15/h1-9H/b3-1+,4-2+

Upstream product

• 129975-62-8 [3-(1,3-dioxolan-2-yl)allyl]phosphonic acid diethyl ester 
• 555-16-8 4-nitrobenzaldehdye 
• 103698-50-6 triphenylarsonium salt of bromoacetaldehyde 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 49678-08-2 3-(4-nitrophenyl)-propenal 
• 16913-46-5 (2E,4E)-5-(4-nitro-phenyl)-penta-2,4-dienoic acid ethyl ester 
• 52509-14-5 (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide 

Relevant academic research and scientific papers

Chalcone Analogue as New Candidate for Selective Detection of α-Synuclein Pathology

Deposition of α-synuclein (α-syn) aggregates is one of the neuropathological hallmarks of synucleinopathies including Parkinson’s disease, dementia with Lewy bodies, and multiple-system atrophy. In vivo detection of α-syn aggregates with SPECT or PET may be an effective tool for medical intervention against synucleinopathy. In the present study, we designed and synthesized a series of chalcone analogues with different aryl groups to evaluate their potential as α-syn imaging probes. In competitive inhibition assays, aryl groups markedly affected binding affinity and selectivity for recombinant α-syn aggregates. Chalcone analogues with a 4-(dimethylamino)phenyl group bound to both α-syn and amyloid β (Aβ) aggregates while ones with a 4-nitrophenyl group displayed α-syn-selective binding. In fluorescent staining, only chalcone analogues with a 4-nitrophenyl group succeeded in selective detection of human α-syn against Aβ aggregates in patients’ brain samples. Among them, PHNP-3 exhibited the most promising binding characteristics for α-syn aggregates (Ki = 0.52 nM), encouraging us to further evaluate its utility. Then, a 125I-labeling reaction was performed to obtain [125I]PHNP-3. In a binding saturation assay, [125I]PHNP-3 bound to α-syn aggregates with high affinity (Kd = 6.9 nM) and selectivity. In a biodistribution study, [125I]PHNP-3 exhibited modest uptake (0.78% ID/g at 2 min after intravenous injection) into a normal mouse brain. Although there is room for improvement of its pharmacokinetics in the brain, encouraging in vitro results in the present study indicate that further structural optimization based on PHNP-3 might lead to the development of a clinically useful probe targeting α-syn aggregates in the future.

Facile Preparation of α-Cyano-α,ω-Diaryloligovinylenes: A New Class of Color-Tunable Solid Emitters

An efficient Knoevenagel condensation reaction was used to construct a series of α-cyano-α,ω-diaryloligovinylenes, which show prominent fluorescence emission in the solid state. On investigating the effect of conjugation length on fluorescent properties,

Imidazole as a central π-linkage in Y-shaped push-pull chromophores

Twelve imidazole based Y-shaped push-pull chromophores have been designed, synthesised and fully characterised featuring 4,5-bis(N,N-dimethylanilino) imidazole as a donor moiety, a systematically enlarged π-linker and nitro and cyano groups as acceptors.

Formation of acetaldehyde enolate from vinyl acetate and its reaction with aromatic and heterocyclic aldehydes: An efficient synthesis of enals and polyenals

Two carbon homologation of aromatic and heterocyclic aldehydes is achieved by reacting them with acetaldehyde enolate anion generated in situ by cleaving vinyl acetate in the presence of barium hydroxide.

Exclusive γ-regio functionalization of crotonaldehyde using γ-trimethylsilyl crotonaldimine. Application to the one pot synthesis of conjugated dienals

Cesium fluoride mediated reaction of γ-trimethylsilyl N-tert-butyl crotonaldimine 9 with a wide range of aldehydes takes place in DMSO at room temperature and affords exclusive γ-regio functionalized products. Heating (rt to 100°C) the δ-silyloxy imines 11 thus obtained leads, after very mild hydrolysis of the tert-butylimine function, to the conjugated dienals 14 in good yields and with excellent (E,E)-selectivities.

Synthesis of (2E,4E)-dienals by double formyl-olefination with an arsonium salt and its application in the syntheses of lipoxygenase metabolites of arachidonic acid

A new facile route to (2E,4E)-dienals by a double formyl-olefination with arsonium salts has been developed. By this method and with other arsonium reagents in the key step some lipoxygenase metabolites of arachidonic acid, lipoxin A4 and B4 and leukotriene B4, have been synthesized.

Polyunsaturated aldehydes by direct polyvinylogation of carbonyl compounds using functionalized phosphonates.

Carbonyl compounds are converted into polyethylenic aldehydes in a one pot reaction with the anions of phosphonates 1. followed by a mild acidic hydrolysis.

Crystal Structure and NMR Spectral Study of (2E,4E)-5-(4-Nitrophenyl)-2,4-pentadienyl and (E)-3-(4-Nitrophenyl)propenal

The structural features of two conjugated aldehydes, (2E,4E)-4-(4-nitrophenyl)-2,4-pentadienal (1, a 'spy dust') and (E)-(4-nitrophenyl)propenal (2), have been studied in the solid state and in solution.X-Ray analysis were performed abd the crystal data are: (1) space group P21/c (No. 14), a = 3.877(3), b = 11.190(6), c = 27.089(9) Angstroem, β = 100.18(5) deg, V = 1156.8 Angstroem3, Z = 4, R = 0.066 for 870 unique observed reflections; (2) space group P21 (No. 4), a = 3.847(2), b = 15.046(3), c = 7.422(3) Angstroem, β = 94.48(2) deg, V = 428(3) Angstroem3, Z = 2, R = 0.047 for 398 unique observed reflections.According to X-ray data, the molecules consist of three planar parts: the slightly deformed aldehyde chain, the benzene ring and the nitro group.The aldehyde chain and the nitro group are coplanar, to within experimental error, while the benzene ring is titled 8(2) deg in compound 1 and 10(2) deg in compound 2 toward the aldehyde chain and the nitro group.The 1H and 13 C NMR chemical shifts and the J(H,H) and J(H,H) values were determined in CDCl3 solution making use of 2-D shift correlated spectra (HH- and CH-COSY).The effects of the electronegative nitro group and the formyl oxygen of the E- and Z-vicinal coupling constants are considered and compared with those of nitro- and chloro-benzene and alkyl-substituted propenals.