17451-00-2

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 118-93-4 o-hydroxyacetophenone 
• 141-97-9 ethyl acetoacetate 
• 87619-10-1 2-[1-Methoxycarbonyl-meth-(Z)-ylidene]-4-methyl-2H-chromene-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and biological screening of thiosemicarbazones of substituted 3-acetylcoumarins having D-glucose moiety

Thiosemicarbazones 5a-j were synthesized with yields of 45–68% by condensation of 3-acetylcoumarins 3a-j and tetra-O-acetyl-β-D-thiosemicarbazide 4. All obtained thiosemicarbazones were screened for anti-microorganic activities against bacteria (B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeruginosa, K. pneumoniae, S. typhimurium) and fungi (A. niger, C. albicans, S. cerevisiae, and A. flavus). Some compounds had significant inhibitory activity with MICs of 0.78–3.125 μM in comparison with 5a, including 5e,h,i for S. aureus, and 5c,f,i for S. epidermidis (Gram-(+) bacteria), 5c,f,g for E.coli, 5f for K. pneumoniae, 5b,c,g for P. aeruginosa, and 5i for S. typhimurium (Gram-(?) bacteria), 5d,h,i for A. niger, 5i for A. flavus, 5b,d,e,h for C. albicans, and 5i for S. cerevisiae. Compounds exhibited excellent activity against tested microorganism with MIC = 0.78 μM, including 5h,i (against S. aureus), 5h (against C. albicans), and 5i (against S. cerevisiae).

Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study

A series of substituted N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)thiosemicarbazones 5a–5j of substituted 3-acetylcoumarins were synthesized with yields of 45–68%. All synthesized thiosemicarbazones were evaluated for cytotoxic activity against several cancer cell lines, such as human breast adenocarcinoma cells MCF7, human liver cancer cells HepG2, human cervical cancer cells HeLa, human melanoma cancer cells SK-Mel-2, and human lung cancer cells LU-1 by using the standard MTT assay. The IC50 values for these cancer cell lines were 1.28–11.81 μM (for MCF-7), 1.53–22.12 μM (for HepG2), 1.43–48.16 μM (for HeLa), 1.82–14.62 μM (for SK-Mel-2), and 1.74–14.62 μM (for LU-1). Most of the compounds were noncytotoxic against human WI-38 normal cell line (IC50 > 16.9 μM). The antiproliferative mechanisms were studied via EGFR inhibition and molecular docking. Docking studies revealed that there are strong interactions between a typical compound with the receptor of the EGFR tyrosine kinase domain with Erlotinib. [Figure not available: see fulltext.]

Synthesis and antimicrobial activity of new linearly fused 6-substituted-3,8-diacetyl-4,7-dimethyl-2H-pyrano[6,5-f]indoles, their chemoselective bromination and synthesis of 3-thiazolylpyranoindoles

When 1-substituted-3,6-diacetyl-5-hydroxy-2-methylindoles 1(a,b) were reacted with ethyl acetoacetate in presence of 2-methylpiperidine produced new 6-substituted-3,8-diacetyl-4,7-dimethyl-2H-pyrano[6,5-f]indole-2-ones 2(a,b). Then these compounds 2(a,b)

REACTIONS OF ALLENE-1,3-DICARBOXYLIC ESTERS AND ACIDS. PART 3. NEW CHROMENE, CHROMONE, QUINOLONE, α-PYRONE AND COUMARIN SYNTHESES

Allene-1,3-dicarboxylic esters and acids have been converted into chromenes, chromones, an α-pyrone and a coumarin by reactions with phenols and to quinolones by reaction with aniline derivatives.A novel chromene --> coumarin rearrangement is also reported.The E and Z stereochemistries of the products have been assigned by n.m.r. measurements.Steric and thermodynamic factors are discussed to account for stereocontrol in product formation.

HETEROCYCLIC SYNTHESES WITH ALLENE-1,3-DICARBOXYLIC ESTERS AND ACIDS : NEW CHROMENE, CHROMONE, QUINOLONE, α-PYRONE AND COUMARIN SYNTHESES

Allene-1,3-dicarboxylic esters and acids have been converted into chromenes, chromones, an α-pyrone and a coumarin by reactions with phenols and to quinolones by reaction with aniline derivatives.A novel chromenecoumarin rearrangement is also reported.