18234-50-9

Upstream product

• 88-15-3 2-Acetylthiophene 
• 90-02-8 salicylaldehyde 

Downstream Products

• 55557-62-5 5-(2-thienyl)-4,5-dihydro-3-(2-hydroxyphenyl)pyrazole 
• 1281979-86-9 C₁₄H₁₃N₃O₂S 
• 1281979-70-1 C₁₉H₁₆N₂OS 
• 1281979-77-8 C₁₉H₁₄N₄O₅S 
• 1365645-08-4 C₁₃H₁₁NO₂S 
• 1365645-12-0 C₁₃H₉NO₂S 
• 1366019-15-9 C₁₉H₁₂N₄O₅S 
• 1366019-44-4 C₁₄H₁₁N₃O₂S 
• 1262757-87-8 C₁₄H₁₃N₃O₂S 
• 1366018-79-2 C₁₉H₁₄N₂OS 
• 1262757-82-3 C₁₉H₁₄N₄O₅S 
• 6297-63-8 2-(2-thienyl)-4H-1-benzopyran-4-one 
• 1443302-03-1 (E)-ethyl 3-(2-((E)-3-oxo-3-(thiophen-2-yl)prop-1-en-1-yl)phenoxy)acrylate 
• 1589534-68-8 C₂₁H₁₆O₃S 

Relevant academic research and scientific papers

Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl ketones

A simple general method for the synthesis of 1-acyl-2-(ortho-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows f

Palladium-Catalyzed Cascade Reactions of 2-(Cyanomethoxy)chalcones with Arylboronic Acids: Selective Synthesis of Emissive Benzofuro[2,3- c]pyridines

The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent selectivity. These transformations involve the domino-style formation of C-C/C-C/C-N bonds through nitrile carbopalladation, intramolecular Michael addition, cyclization, and aromatization. This chemistry allows for the reactions of 2-(cyanomethoxy)chalcones with thiophen-3-ylboronic acid, providing 3-aryl-1-(thiophen-3-yl)benzofuro[2,3-c]pyridines in moderate to good yields. In addition, the resulting products represent a new class of emissive fluorophores.

Apoptosis: A target for anticancer therapy with novel cyanopyridines

One of the many methods of treating cancer is to terminate the uncontrolled growth of cancer cells. So, aiming the apoptotic pathway is an exciting approach to finding new anticancer agents. A novel series of cyanopyridines was designed and synthesized for antiproliferative evaluation. 2-Amino-6-(4-(benzyloxy)phenyl)-4-(4-(dimethylamino)phenyl) nicotinonitrile 10f was the most potent inhibitor against the growth of PC-3, and HepG-2 cancer cell lines with IC50 values of 2.04 uM (selectivity index, SI = 78.63, 43, respectively). Also, 10f was safe against the growth of normal human diploid lung fibroblasts cell line (WI-38) with an IC50 value of 160.04 uM. Its analogs, 10b, 10d, 10g, and 11b, were also active against the growth of PC-3, and HepG-2 while against MCF-7 cell line, they displayed good cytotoxic activity compared to the reference standard 5-FU. Remarkably, mechanistic studies indicated that compounds 10b, 10d, 10f, 10g, and 11b stimulated the level of active caspase 3 and boosted the BAX/BCL2 ratio 20–95 folds in comparison to the control. Our results have also indicated that 10b, 10d, 10f, 10g, and 11b exhibited a very potent inhibitory activity against PIM-1 kinase enzyme, where the IC50 values unraveled very potent molecules in the micromolar range (0.47–1.27 μM). Further investigations have shown that 10f, the most potent PIM-1 kinase inhibitor, induced a cell cycle arrest at the G2/M phase. Moreover, in silico evaluation of ADME properties indicated that all the cyanopyridine compounds are orally bioavailable with no permeation to the blood brain barrier.

Synthesis, characterization, and antioxidant activity of some new benzodiazepine derivatives

A series of novel 4-(substituted phenyl)-2-(2-thienyl)-2,3-dihydro-1H-benzo[b] [1,4] diazepines (MB1-MB8) has been synthesized from 3-(substituted phenyl)-1-(2-thienyl)prop-2-en-1ones (MC1-MC8). The latter compo

Synthesis of 6,12-Methanobenzo[d]pyrano[3,4-g][1,3]dioxocin-1(12H)-ones and Study of Their Interaction with DNA and β-Lactoglobulin

An efficient synthesis of 6,12-methanobenzo[d]pyrano[3,4-g][1,3]dioxocin-1(12H)-ones, a new class of 2,8-dioxabicyclo[3.3.1]nonanes, starting from 2-hydroxychalcones or their analogues and 4-hydroxy-6-methyl-2H-pyran-2-one has been achieved by use of amberlyst-15, a sulfonated polystyrene resin, as a recyclable heterogeneous catalyst. The methodology involves a domino sequence of Michael addition and two-stage heterocyclization. Among the synthesized products, two show significant ct-DNA-binding properties and all show strong binding with the carrier protein β-lactoglobulin (β-lg). A study of antibacterial properties conducted on two bacterial species by using four compounds showed that two of them are moderately active.

Synthesis and selective cytotoxic activities on rhabdomyosarcoma and noncancerous cells of some heterocyclic chalcones

Chemically diverse heterocyclic chalcones were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against rhabdomyosarcoma (RMS) and noncancerous cell line (LLC-PK1). The influence of heteroaryl patte

Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect

2-Amino-3-nitrile-chromenes with potential antitumor activity were constructed by a novel catalytic system. In combination with α-naphthol, quinine could effectively promote the Michael-cyclization process of malononitrile with functionalized chalcones in high yields and moderate to good enantioselectivity (up to 84% ee). It is notable that the enantioselectivity could be greatly improved when α-naphthol was employed as additive.

Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst

A highly enantioselective synthesis of chiral chroman derivatives via an oxa-Michael-Michael cascade reaction has been developed using a bifunctional thiourea organocatalyst. The products were obtained with excellent enantioselectivities (up to >99%), good yields (up to 95%), and diastereoselectivities (up to 5:1).

ZrCl4-catalysed synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridine derivatives

In the presence of a catalytic amount of zirconium(IV) chloride, an efficient synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridines has been developed by the reaction 2-hydroxychalcones with 3-methyl-1-phenyl-1H-pyrazol-5-amine in refluxing ethanol. All these novel compounds have been characterised by 1H NMR, 13C NMR, HRMS, IR spectra and X-ray crystallographic analysis.

Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans

Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.