26845-72-7

Usage

Structure

A derivative of indole with an adamantane group attached to the 2-position of the indole ring.

Properties

Potential pharmaceutical properties, unique structure, and potential biological activities.

Uses

Commonly used in research and drug development, explored for potential effects on the central nervous system, and as a potential drug candidate for the treatment of various disorders.

Upstream product

• 54898-71-4 N-(2-methylphenyl)adamantane-1-carboxamide 
• 5122-82-7 1-adamantyl bromomethyl ketone 
• 62-53-3 aniline 
• 23532-68-5 1-(adamantan-1-yl)-2-bromoethanone 
• 1660-04-4 1-acetyladamantane 
• 100-63-0 phenylhydrazine 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 95-53-4 o-toluidine 
• 1207682-40-3 C₁₈H₂₁NO₃ 
• 2094-72-6 1-Adamantanecarbonyl chloride 

Downstream Products

• 1287714-72-0 2-[2-(1-adamantyl)-1H-indol-3-ylmethyl]-4-nitrophenol 
• 1287714-70-8 2-[2-(1-adamantyl)-1H-indol-3-ylmethyl]phenol 
• 1287714-75-3 5-[2-(1-adamantyl)-1H-indol-3-ylmethyl]-2-hydroxybenzaldehyde 
• 1287714-71-9 2-[2-(1-adamantyl)-1H-indol-3-ylmethyl]-4-bromophenol 

Relevant academic research and scientific papers

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.

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.

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Phosphine ligand 2 - alkyl - indole skeleton as well as preparation method and application thereof

The invention discloses a phosphine ligand 2 - alkyl - indole skeleton and a preparation method and application thereof, wherein the structural formula of the phosphine ligand 2 - alkyl - indole skeleton is shown I. , Wherein R. 1 . R2/su

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.

DFT-Guided Phosphoric-Acid-Catalyzed Atroposelective Arene Functionalization of Nitrosonaphthalene

Guided by computational design, Tan and colleagues disclose a chiral phosphoric-acid-catalyzed asymmetric functionalization of naphthalenes with nitroso as the activating and directing group. This nucleophilic aromatic substitution reaction allows divergent access to two types of axially chiral arylindole frameworks with wide substrate generality under excellent enantiocontrol and, more importantly, offers a facile approach to the privileged NOBIN (2-amino-2′-hydroxy-1,1′-binaphthyl) structures. DFT calculations illustrate the plausible reaction pathway and provide additional insights into the origins of enantioselectivity.Functionalization of arenes represents the most efficient approach for constructing a core backbone of important aryl compounds. Compared with the well-developed electrophilic aromatic substitution and transition-metal-catalyzed C–H activation, nucleophilic aromatic substitution remains challenging because of the lack of a convenient route for rapid conversion of the σH adduct to other stable and versatile intermediates in situ. Guided by computational design, we were able to realize asymmetric nucleophilic aromatic substitution by introducing a nitroso group on naphthalene via chiral phosphoric acid catalysis. This strategy enables efficient construction of atropisomeric indole-naphthalenes and indole-anilines with excellent stereocontrol. Density functional theory (DFT) calculations provide further insights into the origins of enantioselectivity and the reaction mechanisms. The successful application in the synthesis of NOBINs (2-amino-2′-hydroxy-1,1′-binaphthyl) extends the utility of this strategy.Highly efficient conversion of inexpensive and readily available arene materials into high-value-added chiral molecules is of great importance in modern synthetic chemistry given the enormous potential of such structures in functional materials, pharmaceuticals, and other relevant chemical industries. Organocatalytic nucleophilic aromatic substitution enabled by an azo group offers an effective approach to enantioselective functionalization of naphthalene C–H bonds featuring an intramolecular oxidation of an unstabilized σH adduct. Premised on density functional theory (DFT) calculations, nitroso has emerged as another promising activating and oxidative group, whose synthetic potential is substantiated in the atroposelective synthesis of several groups of representative biaryl atropisomers processed by a chiral phosphoric acid catalyst. The success of this reaction explicitly exemplifies the ability of computational tools to streamline organic synthesis with intensified robustness in the disclosed strategy.

Palladium-Catalyzed C–C Ring Closure in α-Chloromethylimines: Synthesis of 1H-Indoles

The C-C ring closure of α-chloromethyl alkyl or aryl N-aryl imines catalyzed with 1 to 10 % Pd(OAc)2/P(p-tolyl)3 afford efficiently 2-aryl- and 2-alkyl-1H-indoles. The heterocyclization reaction involves the initial formation of [2-(arylimino)ethyl]palladium(II) chloride complexes with subsequent C-H activation of the aromatic amine ring. Readily or commercially available α-chloromethyl-aryl or -alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.

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.

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 route to 4-(adamantan-1-yl)quinoline derivatives based on the Friedlaender condensation

2,3,4-Trisubstituted quinolines, substituted with adamantan-1-yl or (adamantan-1-yl)methyl in the 4-position, were prepared from the corresponding admantan-1-yl 2-aminophenyl ketones or admantan-1-ylmethyl 2-aminophenyl ketones and ketones with an α-CHsu