110143-52-7

Usage

InChI:InChI=1/C6H5NO2S/c8-7(9)3-1-6-2-4-10-5-6/h1-5H/b3-1+

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 75-52-5 nitromethane 
• 100-46-9 benzylamine 
• 101756-40-5 2-(thiophen-3-ylmethylene)-malononitrile 

Downstream Products

• 59311-67-0 2-(3-thienyl)ethylamine 
• 1393357-02-2 (5R)-5-methyl-5-((R)-2-nitro-1-(thiophen-3-yl)ethyl)-2-(m-tolyl)oxazol-4(5H)-one 
• 1366043-10-8 (R)-1-benzyl-3-hydroxy-3-((S)-2-nitro-1-(thiophen-3-yl)ethyl)indolin-2-one 

Relevant academic research and scientific papers

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"

We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

Cinchona alkaloid and di-: Tert -butyldicarbonate-DMAP promoted efficient synthesis of (E)-nitroolefins

The synthesis of nitroolefins from aldehydes and olefins is generally limited by the formation of a mixture of cis and trans compounds. Here we report an alternative, metal-free protocol for the synthesis of β-nitroolefins from arylidinemalononitrile using cinchona alkaloid along with di-tert-butyldicarbonate-DMAP in high yields with total selectivity.

Synthesis of (E)-nitroalkenes catalysed by ethanolamine supported on silica

A simple method for preparing (E)-nitroalkenes based on a Henry reaction in the presence of a heterogenized homogeneous catalyst consisting of silica-supported ethanolamine is proposed. With 4-substituted benzaldehydes, the reaction gives the corresponding (E)-nitrostyrenes in high yields and a short time. Heterocyclic carboxaldehydes also give good results, but the presence of an N or S atom in the ring has a slightly adverse effect on the reaction. The synthetic process is quite novel and interesting. The catalyst remains active and exhibits no substantial loss of activity or selectivity over up to three reaction cycles.

Synthesis and biological evaluation of N-acetyl-β-aryl-1,2-didehydroethylamines as new HIV-1 RT inhibitors in vitro

A variety of N-acetyl-β-aryl-1,2-didehydroethylamines were synthesized by direct reduction-acetylation of β-aryl-nitroolefins and assayed as HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the first time. Compound 7a exhibited a TI value of >13.2 with CC50 value of >0.787 mM in C8166 cells. This structure-activity relationship (SAR) study provided a new lead for design and discovery of more potent and selective analogues act as NNRTIs.

TRICYCLIC PYRAZOLE KINASE INHIBITORS

Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

Synthesis of 3,4-diarylpyrroles and conversion into dodecaarylporphyrins; a new approach to porphyrins with altered redox potentials

3,4-Diarylpyrroles (1) have been directly prepared in 20-50% yield by the reaction of β-nitrostyrenes with aqueous TiCl3 in 1,4-dioxane. Pyrroles 1 were also prepared via Barton-Zard pyrrole synthesis using the reaction of α-nitrostilbenes with ethyl isocyanoacetate followed by de-ethoxycarbonylation. 3,4-Diarylpyrroles have been converted into dodecaarylporphyrins by reaction with aromatic aldehydes. Various aryl groups are readily introduced at the periphery of porphyrins by this method. Phenyl substitution at any of the positions of pyrroles decreases E1/2ox while E1/2red is almost unchanged. On the other hand, substitution of the 2-thienyl group affects both the HOMO and LUMO energies, and the UV-vis spectra of dodeca-2-thienylporphyrins (4f or 4i) are extremely red-shifted.

Thieno tetrahydropyridines useful as class III antiarrhythmic agents

This invention relates to thieno tetrahydropyridine and isoquinoline derivative compounds which are useful as antiarrhythmic agents, pharmaceutical compositions comprising such compounds, novel intermediates for their preparation and their methods of use. More particularly these thieno tetrahydropyridine and isoquinoline derivative compounds have been demonstrated to increase the effective refractory period (ERP) of isolated perfused cardiac tissue in vitro.

Aminoethylthiophene derivatives

This invention relates to aminoethylthiophene derivatives and more particularly 2-and 3-aminoethylthiophene derivatives which are useful as antiarrhythmic agents, their methods of use as antiarrhythmic agents, and novel intermediate compounds useful for preparation of the aminoethylthiophene derivatives of the invention.