6590-62-1

Upstream product

• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 100-52-7 benzaldehyde 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 108-86-1 bromobenzene 
• 100-58-3 phenylmagnesium bromide 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 98-80-6 phenylboronic acid 
• 55363-58-1 (3,4,5-trimethoxyphenyl)(phenyl)methanone 

Downstream Products

• 55363-58-1 (3,4,5-trimethoxyphenyl)(phenyl)methanone 
• 1211394-81-8 5-benzyl-1,2,3-trimethoxybenzene 
• 1218781-13-5 C₁₆H₁₇ClO₃ 
• 191677-41-5 1-[(3,4,5-trimethoxyphenyl)(phenyl)methyl]benzotriazole 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 1‐(Diarylmethyl)‐1h‐1,2,4‐triazoles and 1‐(diarylmethyl)‐1h‐imidazoles as a novel class of anti‐mitotic agent for activity in breast cancer

We report the synthesis and biochemical evaluation of compounds that are designed as hybrids of the microtubule targeting benzophenone phenstatin and the aromatase inhibitor letrozole. A preliminary screening in estrogen receptor (ER)‐positive MCF‐7 breast cancer cells identified 5‐((2H‐1,2,3‐triazol‐1‐yl)(3,4,5‐trimethoxyphenyl)methyl)‐2‐methoxyphenol 24 as a potent antiproliferative compound with an IC50 value of 52 nM in MCF‐7 breast cancer cells (ER+/PR+) and 74 nM in triple‐negative MDA‐MB‐231 breast cancer cells. The compounds demonstrated significant G2/M phase cell cycle arrest and induction of apoptosis in the MCF‐7 cell line, inhibited tubulin polymerisation, and were selective for cancer cells when evaluated in non-tumorigenic MCF‐10A breast cells. The immunofluorescence staining of MCF‐7 cells confirmed that the compounds targeted tubulin and induced multinucleation, which is a recognised sign of mitotic catastrophe. Computational docking studies of compounds 19e, 21l, and 24 in the colchicine binding site of tubulin indicated potential binding conformations for the compounds. Compounds 19e and 21l were also shown to selectively inhibit aromatase. These compounds are promising candidates for development as antiproliferative, aromatase inhibitory, and microtubule‐disrupting agents for breast cancer.

Diarylmethanols synthesis by nickel(II)-catalyzed addition of arylboronic acids to aryl aldehydes

A practical procedure for the addition of arylboronic acids to aromatic aldehydes has been developed in the presence of NiCl2(PPh3)2/1,3-bis-(2,6-diisopropylphenyl)imidazolium chloride (IPr·HCl) system with good yield. Generally, electron-rich and-neutral aryl aldehydes showed excellent reactivity and provided desired products in high yields. This procedure will provide new way to the synthesis of diarylmethanols.

Di(hetero)arylmethanol compound preparation method

The invention belongs to the field of organic synthesis, and particularly relates to a di(hetero)arylmethanol compound preparation method, wherein the di(hetero)arylmethanol compound is prepared in ahigh-yield manner by using commercially available (hetero)aryl aldehyde and commercially available (hetero)arylboronic acid as raw materials and using a cheap and stable divalent nickel source as a catalyst. According to the present invention, the method improves the shortcomings of harsh reaction conditions, more side reactions, difficult post-treatment and the like caused by the general use of metal reagents, avoids the defects of high cost of catalytic reactions of noble metals such as palladium and the like and difficulty in mass production, has characteristics of mild conditions, convenient operation, low cost, high efficiency and environmental friendliness, and is suitable for practical scale production.

Employing Arynes for the Generation of Aryl Anion Equivalents and Subsequent Reaction with Aldehydes

Arynes are highly reactive intermediates, which are utilized for the electrophilic arylation of various X-H bonds (X = O, N, S etc.). Herein, a new synthetic strategy is demonstrated, where arynes are converted into aryl anion equivalents by treatment with phosphines and a base. The addition of phosphines to arynes form the phosphonium salts, which in the presence of a carbonate base generates the aryl anion equivalent. Subsequent addition of the aryl anions with aldehydes afforded the secondary alcohols.

Newly synthesized furanoside-based NHC ligands for the arylation of aldehydes

New furanoside-based NHC precursor salts (2) were synthesized using amino alcohols from the chloralose derivatives of glucose (a), galactose (b), and mannose (c). The novel compounds were fully characterized by 1H NMR, 13C NMR, and elemental analyses. The catalytic activities of these salts were tested in the arylation of aldehydes as catalysts that were generated in situ from [RhCl(COD)]2. In addition, 2a was converted to the rhodium complex 3a in order to compare the results obtained in situ. The newly synthesized compounds were very efficient in terms of yield; nevertheless they did not exhibit a chiral induction.

N-heterocyclic carbene-amide rhodium(I) complexes: Structures, dynamics, and catalysis

The amide-functionalized imidazolium salts [BocNHCH2CH 2ImR]X (R = Me, X = I, 1a; R = benzyl, X = Br, 1b; R = trityl, X = Cl, 1c) bearing increasingly bulky N-alkyl substituents were prepared in high yields by direct alkylation of the (2-imidazol-1-yl-ethyl)carbamic acid tert-butyl ester; 1c is a crystalline solid also characterized by X-ray diffraction. These salts are precursors for the synthesis of rhodium(I) complexes [Rh(NBD)X(NHC)] (NHC = 1-(2-NHBoc-ethyl)-3-R-imidazolin-2-ylidene; X = Cl, R = Me (3a), R = benzyl (3b), R = trityl (3c); X = I, R = Me (4a)). All the complexes display restricted rotation about the metal-carbene bond; however, while the rotation barriers calculated for 3a,b and 4a matched the experimental values, unexpectedly this was not true in the case of 3c, where the experimental value was equal to that obtained for compound 3b (58.6 kJ mol-1) and much smaller with respect to the calculated one (100.0 kJ mol-1). The catalytic activity of the neutral rhodium(I) complexes 3a-c in the hydrosilylation of terminal alkynes with HSiMe2Ph has been investigated with PhC≡CH, TolC≡CH, nBuC≡CH, Et 3SiC≡CH, and (CPh2OH)C≡CH as substrates. The steric hindrance on the N-heterocyclic ligand and on the alkyne substrates affects conversion and selectivity: for the former the best results were achieved employing the less encumbered 3a catalyst with TolC≡CH, whereas by employing hindered alkynes such as Et3SiC≡CH or (CPh 2OH)C≡CH the hydrosilylation leads only to the formation of the β-(E)-vinylsilane and α-bis(silyl)alkene isomers. The complexes 3a,b have also been employed in the addition of arylaldehydes with phenylboronic acid, and like in the hydrosylylation case, the best results were obtained using 3a in the presence of aldehydes bearing electron-withdrawing groups, such as 4-cyanobenzaldehyde and 4-acetylbenzaldehyde as substrates.

N-heterocyclic carbene complexes of Rh(I) and electronic effects on catalysts for 1,2-addition of phenylboronic acid to aldehydes

1,3-Diarylsubstituted imidazolinium salts, (NHC-H)Cl, 3, containing hydrogen or alkyl groups at the 4,5-positions of the imidazolidine ring, served as precursors to rhodium(I) complexes [RhCl(NHC)COD], 4, which were converted into cis-[RhCl(NHC)(CO)2] complexes, 5. All compounds prepared were characterized by elemental analyses, 1H NMR and 13C NMR. The relative σ-donor/π-acceptor strength of the NHC ligands was determined by means of IR spectroscopy of 5. The ability of NHCs in 4 to enchance activity was explored in the 1,2-addition of phenylboronic acid to aldehydes. A good correlation was observed between catalytic activity and the electron-donating power of the NHC ligands.

Structure-activity relationships of diphenylpiperazine N-type calcium channel inhibitors

A novel series of compounds derived from the previously reported N-type calcium channel blocker NP118809 (1-(4-benzhydrylpiperazin-1-yl)-3,3-diphenylpropan-1-one) is described. Extensive SAR studies resulted in compounds with IC50 values in the range of 10-150 nM and selectivity over the L-type channels up to nearly 1200-fold. Orally administered compounds 5 and 21 exhibited both anti-allodynic and anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain.

Application of the McMurry coupling reaction in the synthesis of tri- and tetra-arylethylene analogues as potential cancer chemotherapeutic agents

Structural redesign of selected non-steroidal estrogen receptor binding compounds has previously been successful in the discovery of new inhibitors of tubulin assembly. Accordingly, tetra-substituted alkene analogues (21-30) were designed based in part on combinations of the structural and electronic components of tamoxifen and combretastatin A-4 (CA4). The McMurry coupling reaction was used as the key synthetic step in the preparation of these tri- and tetra-arylethylene analogues. The structural assignment of E, Z isomers was determined on the basis of 2D-NOESY experiments. The ability of these compounds to inhibit tubulin polymerization and cell growth in selected human cancer cell lines was evaluated. Although the compounds were found to be less potent than CA4, these analogues significantly advance the known structure-activity relationship associated with the colchicine binding site on β-tubulin.

Synthesis and use of mono- or bisxylyl linked bis(benzimidazolium) bromides as carbene precursors for C-C bond formation reactions

Two benzimidazolium moieties linked by one or two xylyls (m- and p-) have been synthesized, characterized and then they were used for Heck coupling reactions as in situ formed catalysts. Mono bridged salts are more efficient as compared to bisbridged salts. In addition, mono bridged salts were converted to Rh-NHC complexes which were tested as catalysts for the arylation of aldehydes.