73108-75-5

Upstream product

• 82119-79-7 6-phenylchromone-3-carboxylic acid 
• 115560-72-0 3-Hydroxy-3-(4-methoxymethoxy-biphenyl-3-yl)-N,N-dimethyl-propionamide 
• 92-69-3 4-Phenylphenol 
• 127-19-5 N,N-dimethyl acetamide 
• 1761-63-3 2-hydroxy-5-phenylbenzaldehyde 
• 927-80-0 1-ethoxyacetylene 
• 471-25-0 Propiolic acid 
• 1761-61-1 5-bromosalicyclaldehyde 
• 19063-55-9 6-bromo-2H-chromen-2-one 
• 54098-94-1 dimethylphenylborane 
• 115590-28-8 2-(methoxymethoxy)-5-phenylbenzaldehyde 
• 141-32-2 acrylic acid n-butyl ester 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 138116-09-3 2-O-acetyl-4-bromosalicylaldehyde 

Downstream Products

• 1063714-27-1 ethyl 2-amino-4-(2-oxo-2-(piperidin-1-yl)ethyl)-6-phenyl-4Hchromene-3-carboxylate 
• 1063714-28-2 ethyl 2-amino-4-(2-morpholino-2-oxoethyl)-6-phenyl-4H-chromene-3-carboxylate 
• 1063714-30-6 ethyl 2-amino-4-(2-oxo-2-(piperazin-1-yl)ethyl)-6-phenyl-4Hchromene-3-carboxylate 
• 1033753-87-5 ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4H-chromene-3-carboxylate 
• 1063714-82-8 ethyl 2-(2-amino-3-cyano-6-phenyl-4H-chromen-4-yl)acetate 
• 1063714-25-9 isopropyl 2-amino-4-(2-isopropoxy-2-oxoethyl)-6-phenyl-4Hchromene-3-carboxylate 
• 1063714-32-8 ethyl 2-amino-4-(2-(diethylamino)-2-oxoethyl)-6-phenyl-4H-chromene-3-carboxylate 

Relevant academic research and scientific papers

Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions

Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.

Metal-free, Br?nsted acid-mediated synthesis of coumarin derivatives from phenols and propiolic acids

A novel synthesis of coumarin derivatives by Br?nsted acid-mediated condensation and intramolecular cyclization of phenols and propiolic acids was reported. This transformation requires the use of TfOH in place of a conventional metal mediator, and it occurs under mild conditions and provides rapid access to coumarin derivatives in good yields.

Process for preparing coumarin derivatives using phenol and propiolic acid

Provided is a manufacturing method of coumarin derivative. The manufacturing method of coumarin derivative comprises a step of making a phenol compound react with a propiolic acid compound. According to the present invention, the manufacturing method of coumarin derivative is quick and efficient, and is useful to fields requiring synthesis of coumarin derivatives of various structures.COPYRIGHT KIPO 2016

Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins

Cu-catalyzed A3 coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields.

One-pot catalysis of dehydrogenation of cyclohexanones to phenols and oxidative Heck coupling: Expedient synthesis of coumarins

One-pot reactions leading to highly functionalized coumarins have been developed via a Pd(ii)-catalyzed dehydrogenation-oxidative Heck-cyclization process.

Mizoroki-Heck reactions catalyzed by dichloro{bis[1- (dicyclohexylphosphanyl)piperidine]}palladium: Palladium nanoparticle formation promoted by (water-induced) ligand degradation

The palladium-based dichlorobis[1-(dicyclohexylphosphanyl)piperidine] complex - [(P{(NC5H10)(C6H11) 2})2Pd(Cl)2] is readily prepared in quantitative yield from the reaction of [Pd(cod)(Cl)2] (cod=cycloocta-1,5-diene) with two equivalents of 1-(dicyclohexylphosphanyl) piperidine in toluene under N2 within only a few minutes at room temperature. This complex is a highly active Heck catalyst with excellent functional group tolerance, which reliably operates at low catalyst loadings. Various activated, non-activated, deactivated, functionalized, sterically hindered, and heterocyclic aryl bromides, which may contain nitro, chloro or trifluoromethane groups, nitriles, acetales, ketones, aldehydes, ethers, esters, lactones, amides, anilines, phenols, alcohols, carboxylic acids, and heterocyclic aryl bromides, such as pyridines and derivatives, as well as thiophenes and aryl bromides containing methylsulfanyl groups have been successfully coupled with various (also functionalized) alkenes in excellent yields and selectivities (the E-isomers are typically exclusively formed) at 140 °C in the presence of 0.05 mol % of the catalyst in DMF. Even though lower catalyst loadings could be used for many electronically activated, non-activated and some electronically deactivated aryl bromides without noticeable loss of activity, the great advantage of the reaction protocol presented here lies in its reliability and general applicability, which allows its direct adoption to other aryl bromides without the neccessity of its modification. Experimental observations indicated that palladium nanoparticles are the catalytically active form. Consequently, whereas comparable levels of activity were observed for dichloro-bis(aminophosphine) complexes of palladium, a dramatic drop in activity was found for their phosphine-based analogue [(P(C6H 11)3)2Pd(Cl)2]. Copyright

6-arylcoumarins as novel nonsteroidal type progesterone antagonists: An example with receptor-binding-dependent fluorescence

Various 6-arylcoumarin derivatives were designed and synthesized as candidate nonsteroidal type progesterone antagonists. 6-Bromocoumarin derivatives were prepared from the corresponding 4-substituted 2-acetoxy-5-bromobenzaldehyde by employing the Still-Gennari modification of the Horner-Wadsworth-Emmons olefination reaction and were converted to 6-arylcoumarins by means of Suzuki-Miyaura cross-coupling reactions. The biological activities of these coumarin derivatives were evaluated by means of alkaline phosphatase assay in the T47D human breast carcinoma cell line. Among the synthesized compounds, 36 (IC50 = 0.12 μM) and 38 (IC 50 = 0.065 μM), bearing a five-membered heterocycle, showed potent PR antagonist activity. Competitive binding assay showed that compounds 8 and 34 have potent PR binding affinity. The fluorescence of compound 8 was dependent on the solvent properties and was increased in the presence of PR ligand binding domain. This property might be applicable to the development of fluorescence probes for studies on PR.

Synthesis and biological evaluation of (6- and 7-Phenyl) coumarin derivatives as selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1

17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1) is an enzyme that catalyzes NADPH-dependent reduction of the weak estrogen, estrone, into the most potent estrogen, estradiol, which exerts proliferative effects via the estrogen receptors. Overexpression of 17β-HSD1 in estrogen-responsive tissues is related to the development of hormone-dependent diseases, such as breast cancer and endometriosis; thus, 17β-HSD1 represents an attractive target for the development of new therapies. We have discovered that simple coumarines 1 and 2 significantly inhibit 17β-HSD1 in a recombinant enzyme assay, with high selectivity against 17β-HSD2. We postulated that the introduction of various p-substituted phenyl moieties to position 6 or 7 of the coumarin core using the Suzuki-Miyaura cross-coupling reaction would provide mimetics of steroidal structures with improved inhibition of 17β-HSD1. The best inhibitor in the series proved to be 6a, with an IC50 of 270 nM, and with exceptional selectivity for 17β-HSD1 over 17β-HSD2 and against the α and β estrogen receptors.

Structure-activity relationship and molecular mechanisms of ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4H-chromene-3-carboxylate (sHA 14-1) and its analogues

Rapid development of multiple drug resistance against current therapies is a major barrier in the treatment of cancer. Therefore, anticancer agents that can overcome acquired drug resistance in cancer cells are of great importance. Previously, we have demonstrated that ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)-6- phenyl-4H-chromene-3-carboxylate (5a, sHA 14-1), a stable analogue of ethyl 2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (6, HA 14-1), mitigates drug resistance and synergizes with a variety of cancer therapies in leukemia cells. Structure-activity relationship (SAR) studies of 5a guided the development of ethyl 2-amino-6-(3′,5′-dimethoxyphenyl)- 4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (5q, CXL017), a compound with low micromolar cytotoxicity against a wide-range of hematologic and solid tumor cells. More excitingly, our studies of 5q in camptothecin (CCRF-CEM/C2) and mitoxantrone (HL-60/MX2) resistant cancer cells highlight its ability to selectively kill drug-resistant cells over parent cancer cells. 5q inhibits tumor cell growth through the induction of apoptosis, with detailed mechanism of its selectivity toward drug-resistant cancer cells under investigation. These results suggest that 5q is a promising candidate for treatment of cancers with multiple drug resistance. 2009 American Chemical Society.