2555-23-9

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 100-34-5 benzene diazonium chloride 
• 75200-57-6 7-acetoxy-4-methyl-3-phenyl-2H-1-benzopyran-2-one 
• 112030-33-8 4-methyl-3-phenyl-7-phenylacetoxy coumarin 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 
• 63577-89-9 ethyl 2-phenyl-2,3-butadienoate 
• 108-46-3 recorcinol 
• 114-70-5 sodium phenylacetate 
• 5413-05-8 ethyl 2-phenylacetoacetate 
• 4468-48-8 1-phenyl-1-cyanopropan-2-one 

Downstream Products

• 23028-24-2 7-methoxy-4-methyl-3-phenylcoumarin 
• 672938-11-3 8-bromo-7-hydroxy-4-methyl-3-phenyl-coumarin 
• 212694-37-6 6-bromo-7-hydroxy-4-methyl-3-phenyl-coumarin 
• 873403-43-1 6,8-dibromo-7-hydroxy-4-methyl-3-phenyl-coumarin 
• 75200-60-1 7-(1'-Phenyl-2'-p-methoxyphenyl-2'-oxo)-ethyloxy-4-methyl-3-phenylcoumarin 
• 115929-23-2 7-allyloxy-4-methyl-3-phenylcoumarin 
• 135301-04-1 4-methyl-3-phenyl-7-propargyloxycoumarin 
• 75200-58-7 7-O-Desyl-4-methyl-3-phenylcoumarin 
• 179925-52-1 ethyl (4-methyl-3-phenyl-2-oxo-2H-1-benzopyran-7-oxy)acetate 
• 89-86-1 4-hydroxysalicylic acid 
• 103-79-7 1-phenyl-acetone 
• 108-46-3 recorcinol 
• 866887-44-7 7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-4-methyl-3-phenyl-2H-chromen-2-one 
• 179925-55-4 4-methyl-3-phenyl-2-oxo-2H-1-benzopyran-7-oxyacetic acid hydrazide 

Relevant academic research and scientific papers

1,2,3,4-Tetrahydroisoquinoline/2H-chromen-2-one conjugates as nanomolar P-glycoprotein inhibitors: Molecular determinants for affinity and selectivity over multidrug resistance associated protein 1

A series of coniugates bearing a 1,2,3,4-tetrahydroisoquinoline motif linked to substituted 7-hydroxy-2H-chromen-2-ones was synthesized and assayed through calcein-AM test in Madin-Darby Canine Kidney (MDCK) cells overexpressing P-glycoprotein (P-gp) and closely related multidrug resistance associated protein 1 (MRP1) to probe the interference with efflux mechanisms mediated by P-gp and MRP1, respectively. A number of substituents at C3 and C4 of coumarin nucleus along with differently sized and shaped spacers was enrolled to investigate the effects of focused structural modifications over affinity and selectivity. Linker length and flexibility played a key role in enhancing P-gp affinity as proved by the most potent P-gp modulator (3h, IC50 = 70 nM). A phenyl ring within the spacer (3k, 3l, 3o) and bulkier groups (Br in 3r, Ph in 3u) at coumarin C3 led to derivatives showing nanomolar activity (160 nM 50 350). Molecular docking calculations carried out on a human MDR1 homology model structure contributed to gain insights into the ligands’ binding modes. Some compounds (3d, 3h, 3l, 3r, 3t, 3u) reversed MDR thereby restoring doxorubicin cytotoxicity when co-administered with the drug into MDCK-MDR1 cells.

Selective Fluorescent Detection of Cysteine over Homocysteine and Glutathione by a Simple and Sensitive Probe

A simple fluorescent probe able to selectively and sensitively detect cysteine (Cys) with an excellent dose-dependent relationship between fluorescence intensity and concentration of Cys from 0 to 100M has been designed and synthesised.

Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts

This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is

Inhibition of T24 and RT4 human bladder cancer cell lines by heterocyclic molecules

Background: Bladder cancer is a major widespread tumor of the genitourinary tract. Around 30% of patients with superficial cancers develop invasive and metastatic pathology. Material/Methods: Some new heterocyclic 4-methyl coumarin derivatives were design

Regioselective C-3 arylation of coumarins with arylhydrazines via radical oxidation by potassium permanganate

An efficient protocol for oxidative C-3 arylation of coumarins with arylhydrazine has been developed using potassium permanganate as an oxidant. The arylated coumarins with different electronic properties were obtained in moderate to good yields. The deve

Synthesis of substituted coumarins via Bronsted acid mediated condensation of allenes with substituted phenols or anisoles

Coumarins were obtained from the condensation of electron-rich arenes with allenes in the presence of TfOH in good yield. Depending on the substituent pattern of allenes employed, the general synthetic method of 4-substituted and 3,4-disubstituted 3-arylc

Synthesis of flavonoid derivatives of cytisine. 1. Aminomethylation of 7-hydroxy-3-arylcoumarins

Aminomethylation involving the natural alkaloid (-)-cytisine of analogs of natural 3-arylbenzopyran-2-ones was studied. Substituted 8-(cytisin-12-yl) methyl-3-aryl-7-hydroxycoumarins were synthesized.

Discovery and structure-activity relationship of coumarin derivatives as TNF-α inhibitors

The discovery and structure-activity relationship of a novel series of coumarin-based TNF-α inhibitors is described. Starting from the initial lead 1a, various derivatives were prepared surrounding the coumarin core structure to optimize the in vitro inhibitory activity of TNF-α production by human peripheral blood mononuclear cells (hPBMC), stimulated by bacterial lipopolysaccharide (LPS). Selected compounds also demonstrated in vivo inhibition of TNF-α production in rats.

Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3′R,4′R)-3′,4′-di-O-(S)-camphanoyl-(+)-cis- khellactone analogues

A series of disubstituted 3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogues (1-10) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 5-Methoxy-4-methyl DCK (8) was the most promising compound with an EC50 value of 7.21 × 10-6 μM and a therapeutic index of >2.08 × 10,7 which were much better than those of lead compound DCK in the same assay. Another six disubstituted DCK analogues (1-5 and 7) were more potent than AZT but less active than DCK. Conformational analysis suggested that resonance of the coumarin system is an essential structural feature for potent anti-HIV activity. Steric compression of C(4) and C(5) substituents of the coumarin moiety can reduce the overall planarity and thus resonance of the coumarin nucleus, resulting in a decrease or lack of anti-HIV activity.

SYNTHESIS OF 3-ARYLCOUMARINS, 2-AROYLBENZOFURANS AND 3-ARYL-2H-1,4-BENZOXAZINES UNDER PHASE-TRANSFER CATALYSIS CONDITIONS

The synthesis of 3-arylcoumarins, 2-aroylbenzofurans and 3-aryl-2H-1,4-benzoxazines under phase transfer catalysis conditions is described.