175841-30-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 62790-89-0 1-[(tert-butyldimethylsilyl)oxy]-2,6-dimethylbenzene 

Downstream Products

• 947326-53-6 O-(t-butyldimethylsilyl)-2,6-bis(phenylselenylmethyl)phenol 
• 1224868-03-4 2,6-bis[(boronatediphenylphosphanyl)methyl]phenol 

Relevant academic research and scientific papers

Immortalizing a transient electrophile for DNA cross-linking

(Chemical Equation Presented) Who wants to live forever? Compounds that act as strong nucleophiles and good leaving groups repeatedly capture and release a transient quinone methide to extend its effective lifetime under aqueous conditions and promote DNA

Phenyl Selenide-Based Precursors as Hydrogen Peroxide Inducible DNA Interstrand Cross-Linkers

DNA interstrand crosslinks (ICLs) are highly toxic DNA lesions, and induce cell death by blocking DNA strand separation. Most ICL agents aiming to kill cancer cells, also generate adverse side effects to normal cells. H2O2-inducible DNA ICL agents are highly selective for targeting cancer cells, as the concentration of H2O2 is higher in cancer cells than normal cells. Previous studies have focused on arylboronate-based precursors, reacting with H2O2 to generate reactive quinone methides (QMs) crosslinking DNA. Here we explore phenyl selenide-based precursors 1–3 as H2O2-inducible DNA ICL agents. The precursors 1–3 can be activated by H2O2 to generate the good benzylic leaving group and promote production of reactive QMs to crosslink DNA. Moreover, the DNA cross-linking ability is enhanced by the introduction of substituents in the para-position of the phenolic hydroxyl group. From the substituents explored (H, OMe, F), the introduction of electron donating group (OMe) shows a pronounced elevating effect. Further mechanistic studies at the molecular and DNA levels confirm alkylation sites located mainly at dAs, dCs and dGs in DNA. Additionally, cellular experiments reveal that agents 1–3 exhibit higher cytotoxicity toward H1299 human lung cancer cells compared to clinically used drugs, by inducing cellular DNA damage, apoptosis and G0/G1 cell cycle arrest. This study provides a strategy to develop H2O2-inducible DNA interstrand cross-linkers.

Synthesis of oxygen- and sulfur-bridged dirhodium complexes and their use as catalysts in the chemoselective hydrogenation of alkenes

Oxygen-bridged and sulfur-bridged rhodium homobimetallic complexes were synthesized as air-stable crystals by using 2,6-bis(phosphanylmethyl)phenolate and -thiophenolate as the ligands, respectively. The oxygen-bridged dirhodium complex has a symmetrical structure where the carbon atom at the ipso position, oxygen, and two rhodium atoms are located in the same plane. It is thermally stable compared to the sulfur-bridged dirhodium complex and shows catalytic activity for hydrogenation of alkenes with high chemoselectivity.

Synthesis and biological studies of inducible DNA cross-linking agents

(Chemical Equation Presented) Checking the traps: When a phenyl selenide compound such as 1 was oxidized with sodium periodate or irradiated, an ortho-quinone methide intermediate formed and reacted with a DNA duplex by cross-linking. In the crystal structure of a derivative of 1 the biphenyl unit is twisted, and this might explain how 1 can interact effectively with the DNA backbone.