82845-53-2

Upstream product

• 2212-47-7 2,2'-dimethoxy-5,5'-dibromodiphenylmethane 
• 1761-61-1 5-bromosalicyclaldehyde 
• 40102-85-0 2,7-dibromo-9H-xanthen-9-one 
• 56341-31-2 2-bromo-9H-xanthene-9-one 
• 90-47-1 xanth-9-one 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 855289-48-4 5,5'-dibromo-2,2'-dimethoxy-benzophenone 

Downstream Products

• 1316277-21-0 3-[2'-hydroxy-4'-bromophenyl]-5-bromo-1,2-benzisoxazole 
• 1316277-33-4 3-[2'-hydroxy-4'-bromophenyl]-5-bromo-1,2-benzisoxazole 2-oxide 
• 1323153-49-6 C₂₀H₁₄Br₂N₂O₃ 

Relevant academic research and scientific papers

Diastereo- And Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade

We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This N-heterocyclic carbene-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization, as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).

Rh-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones

An efficient rhodium-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones was developed from functionalized salicylaldehydes. This approach provides an easy access to various functionalized 2,2′-dihydroxybenzophenone and xanthone core s

2,2′-Dihydroxybenzophenones and their carbonyl N-analogues as inhibitor scaffolds for MDR-involved human glutathione transferase isoenzyme A1-1

The MDR-involved human GSTA1-1, an important isoenzyme overexpressed in several tumors leading to chemotherapeutic-resistant tumour cells, has been targeted by 2,2′-dihydroxybenzophenones and some of their carbonyl N-analogues, as its potential inhibitors. A structure-based library of the latter was built-up by a nucleophilic cleavage of suitably substituted xanthones to 2,2′-dihydroxy-benzophenones (5-9) and subsequent formation of their N-derivatives (oximes 11-13 and N-acyl hydrazones 14-16). Screening against hGSTA1-1 led to benzophenones 6 and 8, and hydrazones 14 and 16, having the highest inhibition potency (IC50 values in the range 0.18 ± 0.02 to 1.77 ± 0.10 μM). Enzyme inhibition kinetics, molecular modeling and docking studies showed that they interact primarily at the CDNB-binding catalytic site of the enzyme. In addition, the results from cytotoxicity studies with human colon adenocarcinoma cells showed low LC 50 values for benzophenone 6 and its N-acyl hydrazone analogue 14 (31.4 ± 0.4 μM and 87 ± 1.9 μM, respectively), in addition to the strong enzyme inhibition profile (IC50(6 ) = 1,77 ± 0.10 μM; IC50(14 ) = 0.33 ± 0.05 μM). These structures may serve as leads for the design of new potent mono- and bi-functional inhibitors and pro-drugs against human GTSs.

Xanthones in heterocyclic synthesis. An efficient route for the synthesis of C-3 o-Hydroxyaryl substituted 1, 2-benzisoxazoles and their N-oxides, potential scaffolds for angiotensin(II) antagonist hybrid peptides

Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 ohydroxyaryl substituted 1, 2-benzisoxazoles or their V-oxides by cyclodehydration or oxidative cyclization of their corresponding ketoxime precursors, respectively. Molecular modeling analysis and 1H NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom. The Japan Institute of Heterocyclic Chemistry.

Xanthones in heterocyclic synthesis. An efficient and general route for the synthesis of regioselectively substituted phthalazines

Xanthone undergoes regioselective substitution and nucleophically - triggered ring opening to the corresponding ketone. Hydrazone of the latter oxidatively rearranges to ortho-diacylarenes, which, then, with hydrazine gives regioselectively substituted phthalazines. Molecular modeling analysis and 1HNMR spectra indicate an intramolecular H-bonding engaging phenol OH and phthalazine N-3 atom.