220235-72-3

Upstream product

• 768-95-6 1-adamanthanol 
• 100867-01-4 (4-methoxybenzyl)(4-nitrophenyl)sulfane 
• 768-94-5 1-Adamantanamine 
• 56916-85-9 N-[(4-methoxyphenyl)methyl]adamantan-1-amine 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 768-95-6 1-adamanthanol 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Preparation of Alkyl Ethers with Diallyltriazinedione-Type Alkylating Agents (ATTACKs-R) Under Acid Catalysis

Diallyltriazinedione-type acid-catalyzed alkylating agents (ATTACKs-R) with 10 different alkyl groups (R), including benzyl, substituted benzyl, allyl, and methyl groups were synthesized. The palladium-catalyzed intramolecular O-to-N allylic rearrangement of 2,4-bis(allyloxy)-6-chloro-1,3,5-triazine was developed to introduce various alkoxy groups into the N,N′-dialkylated triazinedione skeleton. O-Alkylation of alcohols with ATTACKs-R was carried out in 1,4-dioxane in the presence of 2,6-di-tert-butylpyridinium trifluoromethanesulfonate or trifluoromethanesulfonic acid as a catalyst. Six selected ATTACKs-R bearing benzylic R groups were employed to prepare alkyl ethers from primary, secondary, and tertiary alcohols. The reactions of ATTACKs-R bearing an o-nitro-substituted benzyl group tended to afford low yields. Comparison of four different triazinedione-based benzylating reagents suggested that the N,N′-substituents affected the reactivity.

Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis

An efficient and greener deprotection method for p-methoxybenzyl (PMB) ethers using a metal-free visible light photoredox catalyst and air and ammonium persulfate as the terminal oxidants is presented. Various functional groups and protecting groups were tolerated in the developed method to achieve good to excellent yields in short reaction times. Significantly, the developed method was compatible with PMB ethers derived from primary, secondary, and tertiary alcohols and a gram-scale reaction. Mechanistic studies support a proposed reaction mechanism that involves single electron oxidation of the PMB ether.

Discovery of novel dual inhibitors of the wild-type and the most prevalent drug-resistant mutant, S31N, of the M2 proton channel from influenza A virus

Anti-influenza drugs, amantadine and rimantadine, targeting the M2 channel from influenza A virus are no longer effective because of widespread drug resistance. S31N is the predominant and amantadine-resistant M2 mutant, present in almost all of the circulating influenza A strains as well as in the pandemic 2009 H1N1 and the highly pathogenic H5N1 flu strains. Thus, there is an urgent need to develop second-generation M2 inhibitors targeting the S31N mutant. However, the S31N mutant presents a huge challenge to drug discovery, and it has been considered undruggable for several decades. Using structural information, classical medicinal chemistry approaches, and M2-specific biological testing, we discovered benzyl-substituted amantadine derivatives with activity against both S31N and WT, among which 4-(adamantan-1-ylaminomethyl)-benzene-1,3-diol (44) is the most potent dual inhibitor. These inhibitors demonstrate that S31N is a druggable target and provide a new starting point to design novel M2 inhibitors that address the problem of drug-resistant influenza A infections.