54898-71-4

Upstream product

• 2094-72-6 1-Adamantanecarbonyl chloride 
• 95-53-4 o-toluidine 
• 828-51-3 1-Adamantanecarboxylic acid 

Downstream Products

• 26845-72-7 2-((3r,5r,7r)adamantan-1-yl)-1H-indole 

Relevant academic research and scientific papers

Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols

Presented here is a class of novel axially chiral aryl-p-quinones as platform molecules for the preparation of non-C2 symmetric biaryldiols. Two sets of aryl-p-quinone frameworks were synthesized with remarkable enantiocontrol by means of chiral phosphoric acid catalyzed enantioselective arylation of p-quinones by central-to-axial chirality conversion. These aryl-p-quinones were then used to access a wide spectrum of highly functionalized non-C2 symmetric biaryldiols with excellent retention of the enantiopurity.

Catalytic Synthesis of N-Aryladamantane-1-carboxamides Using Phosphorus Trichloride

Abstract: N-Aryl(benzyl)adamantane-1-carboxamides were synthesized in 54–87% yields by reaction of adamantane-1-carboxylic acid with aromatic amines in the presence of phosphorus trichloride, 4-dimethylaminopyridine, and triethylamine on heating at 80°C for 8 h.

Synthesis and biological evaluation of 1-(2-(adamantane-1-yl)-1: H -indol-5-yl)-3-substituted urea/thiourea derivatives as anticancer agents

The indole ring, adamantane, and urea groups are important components of bioactive molecules. The orphan nuclear receptor Nur77 as a unique transcription factor encoded by an immediate early gene is a potential therapeutic target for cancer treatment. We synthesized a series of 1-(2-(adamantane-1-yl)-1H-indol-5-yl)-3-substituted urea/thiourea derivatives and identified which of these potential anticancer candidates could modulate the expression and activity of Nur77. The synthesized compounds were initially evaluated for their anti-proliferative activity against H460 lung cancer cells, HepG2 liver cancer cells, and MCF-7 breast cancer cells. Major compounds were found to be active against these tested cancer cell lines. The compounds with IC50 values down to 20 μM exhibited selective cytotoxicity effects on the human lung cancer cell line (H460) and the normal lung cell line (MCR-5). Compounds 7n, 7s, and 7w induced Nur77-expression in a time- and dose-dependent manner in H460 cells. Compounds 7n and 7s strongly induced Parp cleavage in H460 cells, but 7w resulted in a slight induction of apoptosis. The apoptotic effect of 7s was largely inhibited when the Nur77 was knocked down by shRNA. This indicated that Nur77 served as a critical mediator for the anticancer action of 7s. The molecular docking study between Nur77 and 7s revealed that compound 7s exhibited a promising binding affinity with Nur77. These findings will provide a direction for the developing Nur77 regulator as anticancer agents.

1-(2-(adamantane-1-yl)-1H-indole-5-yl)-3-substituted urea derivative, preparation and use thereof

Relating to urea derivatives containing an indole structure, the invention provides a 1-(2-(adamantane-1-yl)-1H-indole-5-yl)-3-substituted urea derivative, preparation and use thereof. The preparation method includes: 1) synthesis of 2'-methyl adamantane anilide; 2) preparation of intermediate 2-adamantane-1H-indole; 3) preparation of intermediate 2-adamantane-5-nitro-1H-indole; 4) preparation of intermediate 2-adamantane-5-amino-1H-indole; 5) preparation of intermediate 2-adamantane-5-isocyanate-1H-indole; and 6) preparation of 1-(2-(adamantane-1-yl)-1H-indole-5-yl)-3-substituted urea derivative. The 1-(2-(adamantane-1-yl)-1H-indole-5-yl)-3-substituted urea derivative can be applied in preparation of drugs treating tumors. According to the invention, the reaction cost is low, the yield is high, and the reaction process is simple and easy to control.

Novel N-substituted 2-(2-(adamantan-1-yl)-1H-indol-3-yl)-2-oxoacetamide derivatives: Synthesis and biological evaluation

In this study, a series of novel N-substituted 2-(2-(adamantan-1-yl)-1H-indol-3-yl)-2-oxoacetamide derivatives were synthesized, and evaluated for their cytotoxicity in human cell lines including Hela (cervical cancer), MCF7 (breast cancer ) and HepG2 (liver cancer). Several compounds were found to have potent anti-proliferative activity against those human cancer cell lines and compound 5r showed the most potent biological activity against HepG2 cells with an IC50 value of 10.56 ± 1.14 μM. In addition, bioassays showed that compound 5r induced time-dependent and dose-dependent cleavage of poly ADP-ribose polymerase (PARP), and also induced a dose-dependent increase in caspase-3 and caspase-8 activity, but had little effect on caspase-9 protease activity in HepG2 cells. These results provide evidence that 5r-induced apoptosis in HepG2 cell is caspase-8-dependent.

Synthesis, structure–activity relationship studies and biological evaluation of novel 2,5-disubstituted indole derivatives as anticancer agents

Three novel series of 2,5-disubstituted indole derivatives were synthesized and evaluated in vitro for their antiproliferative activity against human cancer cells and HIV-1 inhibition activity used as a readout of cellular activity. Most compounds were found to have potent anticancer activity. In particular, 2c and 3b which showed effectively to repress HIV-1 transcription had a pan antiproliferative activity in cervical cancer cells (HeLa), breast cancer cells (MCF-7), liver cancer cells (HepG2), and lung cancer cells (H460 and A549). While 3b exhibited high sensitivity to A549 cells with the IC50 value 0.48?±?0.15?μm, 2c showed high selectivity toward HepG2 cells with the IC50 value 13.21?±?0.30?μm. With respect to the cellular mechanism of action, HepG2 cells treated with 2c and A549 cells treated with 3b for 24?h were studied by annexin V/PI staining and Western blot analysis, and results revealed that 2c and 3b may induce cancer cells apoptosis through inhibiting the phosphorylation at Ser2 of RNAPII CTD which can be phosphorylated by cyclin-dependent kinase 9. These studies indicated that 2c and 3b may develop as potent lead compounds in the therapy of cancer. However, determining their roles in preventing HIV-1 still requires further intensive study.

Lithiation of N-(2-Alkylphenyl)alkanamides and Related Compounds. A Modified Madelung Indole Synthesis

A modified Madelung synthesis for the conversion of N-(alkylphenyl)alkanamides and related compounds to indoles, benzindoles, and azindoles has been developed.This procedure consists of treating the amide with 2 or 3 equiv of n-butyllithium or lithium diisopropylamide in tetrahydrofuran at temperatures from -20 to +25 deg C.Several examples where products other than indoles were formed from the starting amide are also reported.

2-Substituted indoles and process for their preparation

Highly branched α-substituted indoles, e.g., 2-(1-methylcyclohexyl)-indole, are prepared by treating N-(α-branched carbonyl) toluidines with alkyl lithium. The reaction sequence may be illustrated as SPC1