110827-84-4

Upstream product

• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 120-80-9 benzene-1,2-diol 

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• 67984-81-0 2,3-dihydroxybenzonitrile 

Relevant academic research and scientific papers

Solution and Solid State Study on the Recognition of Hydroxyaromatic Aldoximes by Nitrogen Containing Compounds

Structural aspects and fluorescence behaviors of a series of cocrystals of hydroxyaromatic aldoximes, namely, 2(H2NAP)·(4,4′-bipyridine), 2(H2NAP)·(HMTA), H2NAP·caffeine, and (H3OHPA)·theophylline·2H2

Synthesis, Structural, and Physicochemical Characterization of a Ti6and a Unique Type of Zr6Oxo Clusters Bearing an Electron-Rich Unsymmetrical {OON} Catecholate/Oxime Ligand and Exhibiting Metalloaromaticity

The chelating catechol/oxime ligand 2,3-dihydroxybenzaldehyde oxime (H3dihybo) has been used to synthesize one titanium(IV) and two zirconium(IV) compounds that have been characterized by single-crystal X-ray diffraction and 1H and 13C NMR, solid-state UV-vis, and ESI-MS spectroscopy. The reaction of TiCl4 with H3dihybo and KOH in methanol, at ambient temperature, yielded the hexanuclear titanium(IV) compound K2[TiIV6(μ3-O)2(μ-O)3(OCH3)4(CH3OH)2(μ-Hdihybo)6]CH3OH (1), while the reaction of ZrCl4 with H3dihybo and either nBu4NOH or KOH also gave the hexanuclear zirconium(IV) compounds 2 and 3, respectively. Compounds 1-3 have the same structural motif [MIV6(μ3-?)2(μ-?)3] (M = Ti, Zr), which constitutes a unique example with a trigonal-prismatic arrangement of the six zirconium atoms, in marked contrast to the octahedral arrangement of the six zirconium atoms in all the Zr6 clusters reported thus far, and a unique Zr6 core structure. Multinuclear NMR solution measurements in methanol and water proved that the hexanuclear clusters 1 and 3 retain their integrity. The marriage of the catechol moiety with the oxime group in the ligand H3dihybo proved to be quite efficient in substantially reducing the band gaps of TiO2 and ZrO2 to 1.48 and 2.34 eV for the titanium and zirconium compounds 1 and 3, respectively. The application of 1 and 3 in photocurrent responses was investigated. ESI-MS measurements of the clusters 1 and 3 revealed the existence of the hexanuclear metal core and also the initial formation of trinuclear M3 (M = Ti, Zr) building blocks prior to their self-assembly into the hexanuclear M6 (M = Ti, Zr) species. Density functional theory (DFT) calculations of the NICSzz scan curves of these systems revealed that the triangular M3 (M = Ti, Zr) metallic ring cores exhibit pronounced metalloaromaticity. The latter depends upon the nature of the metallic center with NICSzz(1) values equal to-30 and-42 ppm for the Ti (compound 1) and Zr (compound 2) systems, respectively, comparable to the NICSzz(1) value of the benzene ring of-29.7 ppm calculated at the same level of theory.

A study on fluoride detection and assembly of hydroxyaromatic aldoximes caused by tetrabutylammonium fluoride

Tetrabutylammonium fluoride (TBAF) forms cocrystal H2NAP·TBAF with 2-hydroxynaphthaldoxime (H2NAP) or cocrystal 2(H3OHPA)·TBAF with 2,3-dihydroxyphenylaldoxime (H3OHPA), whereas a similar reaction with 2,4-dihydroxyphenylaldoxime (H3PHPA) forms tetrabutylammonium (TBA) salt TBA(H2.5PHPA)2. Formation of these cocrystals or salts is accompanied by a color change which enables the detection of fluoride ions. Cocrystal H2NAP·TBAF has a layered structure formed by hydrogen bonds between the fluoride ions and parent oxime molecules; the tetrabutylammonium cations are held in between layers of anionic assemblies. On the other hand, cocrystal 2(H3OHPA)·TBAF has a grid-like architecture constructed from hydrogen bonds between the parent oxime molecules and fluoride ions. TBA cations are encapsulated within the grids. It is shown that salt TBA(H2.5PHPA)2 forms anionic assemblies to encapsulate tetrabutylammonium cations which are devoid of fluoride ions. By interactions of the tetrabutylammonium fluoride ions with H3PHPA molecules, an anionic assembly is formed by the sharing of protons, which possesses a grid-like structure. The formation of such an assembly causes color change which enables one to detect fluoride ions by visual means. This journal is

Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis

Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.

Reactivity and mechanism of α-nucleophile scaffolds as catalytic organophosphate scavengers

Despite their unique benefits imparted by their structure and reactivity, certain α-nucleophile molecules remain underexplored as chemical inactivators for the topical decontamination of reactive organophosphates (OPs). Here, we present a library of thirty α-nucleophile scaffolds, each designed with either a pyridinium aldoxime (PAM) or hydroxamic acid (HA) α-nucleophile core tethered to a polar or charged scaffold for optimized physicochemical properties and reactivity. These library compounds were screened for their abilities to catalyze the hydrolysis of a model OP, paraoxon (POX), in kinetic assays. These screening experiments led to the identification of multiple lead compounds with the ability to inactivate POX two- to four-times more rapidly than Dekon 139 - the active ingredient currently used for skin decontamination of OPs. Our mechanistic studies, performed under variable pH and temperature conditions suggested that the differences in the reactivity and activation energy of these compounds are fundamentally attributable to the core nucleophilicity and pKa. Following their screening and mechanistic studies, select lead compounds were further evaluated and demonstrated greater efficacy than Dekon 139 in the topical decontamination of POX in an ex vivo porcine skin model. In addition to OP reactivity, several compounds in the PAM class displayed a dual mode of activity, as they retained the ability to reactivate POX-inhibited acetylcholine esterase (AChE). In summary, this report describes a rationale for the hydrophilic scaffold design of α-nucleophiles, and it offers advanced insights into their chemical reactivity, mechanism, and practical utility as OP decontaminants.

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki-Miyaura coupling reactions of aryl chlorides

A series of N,O-bidentate ligands were synthesized using the Vilsmeier-Haack reaction and oximation. 2,5-Dihydroxyterephthalaldehyde dioxime (L8) as an efficient N,O-symmetrical bidentate ligand was prepared from hydroquinone. It was studied as a high activity ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions. The coupling reactions were performed in the presence of PdCl2 as the catalyst, L8 as the ligand, Na2CO3 as the base, PEG-400 as the PTC and in ethanol/water (1?:?1) as an environmentally benign solvent at 85 °C. Plentiful biaryls were obtained by the optimized reaction with good yields at a low palladium loading of 0.20 mol%.

Hydroxy- or methoxy-substituted benzaldoximes and benzaldehyde-O-alkyloximes as tyrosinase inhibitors

Several benzaldoximes, benzaldehyde-O-ethyloximes, and acetophenone-oximes were synthesized and evaluated as tyrosinase inhibitors by an assay based on tyrosinase catalyzed L-DOPA oxidation. Whereas benzaldoxime itself is only a weak inhibitor, its deriva