25784-85-4

Usage

InChI:InChI=1/C9H9NO3S/c1-7(11)6-14-9-4-2-8(3-5-9)10(12)13/h2-5H,6H2,1H3

Upstream product

• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 67-64-1 acetone 
• 1219622-14-6 S-adenosyl-S-(propan-2-one)-L-methionine 
• 485-80-3 S-adenosyl-L-methionine 
• 1849-36-1 para-nitrobenzenethiol 
• 100-00-5 4-chlorobenzonitrile 
• 123-54-6 acetylacetone 
• 78-95-5 chloroacetone 

Downstream Products

• 19822-11-8 1-(4-nitrophenylsulfonyl)-2-propanone 
• 17514-62-4 3-Methyl-5-nitro-benzothiophen 
• 1166403-30-0 (S)-1-(4-nitrophenyl)thiopropan-2-ol 

Relevant academic research and scientific papers

Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Crystal structure, DFT study and catalytic investigation of palladium and nickel complexes towards deacylative sulfenylation of active methylenes and regioselective 3-sulfenylation of indoles: Via thiouronium salt formation

A series of Ni(ii), Cu(ii), Co(ii), and Pd(ii) complexes have been synthesized with a chelating Schiff base ligand coordinated to a metal center with ONS donor atoms. The ligand and complexes are characterized by elemental analysis and spectroscopic techniques like FT-IR, 1H-NMR, and UV-Visible spectroscopy. The single crystal structure of the Pd(ii) complex is obtained by X-ray diffraction analysis and exhibits slightly distorted square planar geometry. The structure is optimized by DFT, TD-DFT calculation to elaborate the electronic structure and NBO for the charge distribution analysis of the Pd(ii) complex. The synthesized Pd(ii) and Ni(ii) complexes as catalysts have been investigated in the C-S cross-coupling of indoles and active methylenes. The metal propelled regioselective transformation afforded 3-sulfenylated indoles while β-diketones favored deacylated monosulfenyl ketones in an excellent yield via thiouronium salt formation. The Pd(ii) complex displays slightly better reactivity whereas the Ni(ii) complex is cost-efficient. The method is fast, easy to handle and cost effective in terms of high reactivity of catalysts, use of non-toxic solvents, and cheaper aryl halides and thiourea replace conventional sulfur sources, providing a practical access to organic transformations.

Design and synthesis of new RAF kinase-inhibiting antiproliferative quinoline derivatives. Part 2: Diarylurea derivatives

This article describes the design, synthesis, and biological screening of a new series of diarylurea derivatives possessing quinoline nucleus. Nine target compounds were selected by the National Cancer Institute (NCI, Bethesda, Maryland, USA) for in?vitro antiproliferative screening against a panel of 58 cancer cell lines of nine cancer types. Following one-dose initial screening, compounds 1d-g and 2b were selected for 5-dose screening in order to calculate their IC50and total growth inhibition (TGI) values against the cell lines. Compounds 1e and 1g were the most promising analogues. Both compounds showed strong potency and broad-spectrum antiproliferative activity against the different tested cancer types. Their IC50and TGI values were less than those of the reference drug, sorafenib, against most of the tested cell lines of the nine different cancer types. Furthermore, the most potent compounds 1d-g were tested against C-RAF kinase as a potential molecular target of this series of compounds. All of them showed high potency, and the most potent derivative was compound 1e (IC50?=?0.10?μM). It was further tested against a panel of another twelve kinases, and it showed selectivity against C-RAF kinase. This could be, at least in part, the possible mechanism of antiproliferative action of this series of compounds at molecular level. The binding modes of compounds 1e and 1g were studied by docking studies, which highlighted the importance of the urea linker compared with the amide linker.

Enzyme-catalyzed transfer of a ketone group from an S-adenosylmethionine analogue: A tool for the functional analysis of methyltransferases

"Chemical equation presented" S-Adenosylmethionine (AdoMet or SAM)-dependent methyltransferases belong to a large and diverse family of group-transfer enzymes that perform vital biological functions on a host of substrates. Despite the progress in genomics, structural proteomics, and computational biology, functional annotation of methyltransferases remains a challenge. Herein, we report the synthesis and activity of a new AdoMet analogue functionalized with a ketone group. Using catechol O-methyltransferase (COMT, EC 2.1.1.6) and thiopurine S-methyltransferase (TPMT, EC 2.1.1.67) as model enzymes, this robust and readily accessible analogue displays kinetic parameters that are comparable to AdoMet and exhibits multiple turnovers with enzyme. More importantly, this AdoMet surrogate displays the same substrate specificity as the natural methyl donor. Incorporation of the ketone group allows for subsequent modification via bio-orthogonal labeling strategies and sensitive detection of the tagged ketone prod cts. Hence, this AdoMet analogue expands the toolbox available to interrogate the biochemical functions of methyltransferases.

Aromatic sulfonyl alpha-hydroxy hydroxamic acid compounds

An aromatic sulfonyl alpha-hydroxy hydroxamic acid compound that, inter alia, inhibits matrix metalloprotease activity is disclosed, as is a treatment process that comprises administering a contemplated aromatic sulfonyl alpha-hydroxy hydroxamic acid comp

New hypoxia-selective cytotoxines derived from quinoxaline 1,4-dioxides

A new series of quinoxaline 1,4-dioxides, structurally related to the benzotriazine tirapazamine 1 have been prepared starting from 5,6-dichlorobenzofuroxane 2. The Beirut reaction between 2 and alkyl or aryl thiopropanones afforded the 2-methyl-3-alkyl(a

CONFORMATIONAL AND ELECTRONIC INTERACTION STUDIES OF α-SUBSTITUTED CARBONYL COMPOUNDS. VI. p-SUBSTITUTED α-PHENYLTHIOACETONES.

The analysis of the νCO bands in the I.R. spectrum of p-substituted α-phenylthioacetones indicates a cis/gauche rotational isomerism.The slight solvent effect on the αc αg ratios on going from a non polar solvent to a polar one , for the title compounds, as well as the minute sensitivity of the νCO (cis) frequencies on going from electron-attracting to electron-donating substituents are interpreted on the grounds of the Field (F) and Inductive effects, which act in opposition in the cis rotamer, practically cancelling each other.The decreasing cis/gauche population ratio on going from electron-attracting to electron-donating substituents suggests the occurance of the hyperconjugative interaction in the gauche rotamers of the title compounds.The progressive shielding effect on the methylene and carbonyl carbon atoms in the 13C NMR spectra, on going from electron-donating to electron-attracting substituents is ascribed at least in part, to the "Reverse Polar Effect".Keywords: Conformational studies; electronic interaction; Reverse Polar Effect; I.R. spectroscopy; 13C NMR spectroscopy; p-substituted α-phenylthioacetones.

Determination of potentially mutagenic and carcinogenic electrophiles in environmental samples

Direct acting mutagens are common in many types of environmental samples. Most direct acting mutagens are electrophiles. The nucleophile 4-nitrothiophenol reacts readily with electrophilic alkyl halides and epoxides to form thioethers which have absorptio