21071-42-1

Upstream product

• 87050-71-3 4,4'-Dimethyl-2,2',5,5'-tetramethoxy-stilben 
• 4925-88-6 2,5-dimethoxy-4-methylbenzaldehyde 
• 25224-33-3 (2,5-dimethoxy-4-methylbenzyl)triphenylphosphonium chloride 

Downstream Products

• 87050-81-5 trans-1,2-bis(2,5-dimethoxy-p-tolyl)cyclopropane 
• 87050-72-4 (E)-1,2-bis[4-(bromomethyl)-2,5-dimethoxyphenyl]ethene 
• 87050-73-5 (E)-1,2-bis<4-<(acetyloxy)methyl>-2,5-dimethoxyphenyl>ethene 
• 17228-87-4 1,2-bis(2,5-dimethoxy-p-tolyl)ethane 

Relevant academic research and scientific papers

Acid catalysis vs. electron-transfer catalysis via organic cations or cation-radicals as the reactive intermediate. Are these distinctive mechanisms?

Proton transfer to aromatic and olefinic donors (D) leads to the facile interchange of transient carbocations (DH+) and cation-radical (D+.). The same types of cation and cation-radical are reactive intermediates in the acid catalysis and the electron-transfer catalysis of such organic transformations as benzylic coupling, epoxide/pinacol rearrangements and cis-trans isomerization of stilbenes when they are both carried out under otherwise identical reaction conditions. However, the rapid exchange of diamagnetic cations and paramagnetic cation-radicals blurs the traditional view of separate electrophilic and homolytic processes, and rigorous experimental evidence is required to establish whether acid catalysis and electron-transfer catalysis actually represent distinct mechanistic categories. Acta Chemica Scandinavica 1998.

Bis(bioreductive) alkylating agents: Synthesis and biological activity in a nude mouse human carcinoma model

Chemical investigations leading to the construction of bis(bioreductive) alkylating agents having both conformationally restricted and mobile spacer regions are described. Two targets having the conformationally mobile ethylene spacer group, namely, 2,2'-ethylenebis[6-(hydroxymethyl)-p-benzoquinone] diacetate (3b) and 2,2'-ethylenebis[6-(bromomethyl)-p-benzoquinone] (3c), were studied in vivo and in vitro using an established epithelial/Burkitt lymphoma hybrid cell line (D98/HR1) previously shown to induce carcinomas in nude mice. Inactivity of both test compounds in vitro, the relative resistance of these cells to test drugs in vitro, and the selective antitumor properties of the bis(bromomethyl) analogue in vivo lead to the proposal that this compound undergoes bioreduction to an alkylating species in the hypoxic core of the tumor, thereby exerting its action.