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Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE is used as a building block for the synthesis of various pharmaceuticals and medical treatments. Its versatility as an intermediate allows for the development of a wide range of drugs, contributing to advancements in healthcare.
Used in Organic Synthesis:
1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE is used as a reagent in organic synthesis for various chemical reactions. Its unique properties enable it to facilitate the formation of desired products, making it an essential component in the synthesis of complex organic compounds.
Used in Dyes and Pigments Industry:
1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE is used in the manufacture of dyes and pigments. Its chemical properties allow for the creation of a variety of colorants, contributing to the diversity of colors available in various industries.
Used in Antimicrobial and Antiviral Applications:
1,2,3,4,9,10-HEXAHYDROACRIDIN-9-ONE has been studied for its potential antimicrobial and antiviral properties. Its ability to inhibit the growth of certain microorganisms and viruses makes it a promising candidate for use in the development of new antimicrobial and antiviral treatments.

InChI:InChI=1/C13H13NO/c15-13-9-5-1-3-7-11(9)14-12-8-4-2-6-10(12)13/h1,3,5,7H,2,4,6,8H2,(H,14,15)

Upstream product

• 14807-16-0 9-Anilino-1,2,3,4-tetrahydroacridine 
• 38778-79-9 ethyl 2-(N-phenylamino)-1-cyclohexene-1-carboxylate 
• 108-94-1 cyclohexanone 
• 118-92-3 anthranilic acid 
• 139518-61-9 3,3'-bis(spiro-4'(3'H)-one) 
• 96447-10-8 spiro<2H-3,1-benzoxazine-2,1'-cyclohexan>-4(1H)-one 
• 68-12-2 N,N-dimethyl-formamide 
• 111232-51-0 10-(4-methoxybenzyl)-1,2,3,4,9,10-hexahydroacridin-9-one 
• 109072-21-1 2-Cyclohexylideneamino-N,N-diethyl-benzamide 
• 134-20-3 2-carbomethoxyaniline 
• 3898-08-6 1,1-diphenylthiourea 
• 6833-04-1 N,N'-Diphenylpimelamide 
• 2047-89-4 5,6,7,8,9,10-hexahydrocyclohept[b]indole 
• 62-53-3 aniline 

Downstream Products

• 5396-30-5 9-chloro-1,2,3,4-tetrahydroacridine 
• 443662-39-3 7-bromo-1,2,3,4-tetrahydro-acridin-9-ol 
• 578-95-0 10H-acridin-9-one 
• 260-94-6 acridine 
• 56717-04-5 1,2,3,4-tetrahydroacridin-9-ol 
• 6526-92-7 2,7-Dimethoxy-9-chloroacridine 

Relevant academic research and scientific papers

Visible-Light Cascade Photooxygenation of Tetrahydrocarbazoles and Cyclohepta[b]indoles: Access to C,N-Diacyliminium Ions

Tetrahydrocarbazoles and perhydrocyclohepta[b]indoles undergo a catalytic cascade singlet oxygenation in alkaline medium, which leads to chiral tricyclic perhydropyrido- and perhydroazepino[1,2-a]indoles in a single operation. These photooxygenation products are new synthetic equivalents of uncommon C,N-diacyliminium ions and can be functionalized with the aid of phosphoric acid organocatalysis.

Reactivity of β-cetoesters compounds, synthesis of nitrogenated heterocycles (derivatives of tetrahydroacridin-9-ones and pyrimidinone) and biological properties of pyrimidinone derivatives

Ethyl 2-oxocyclohexanecarboxylate has undergone smooth condensation with arylamines under ethanol. The corresponding β-enaminoesters compounds were obtained in good yields. These compounds were then refluxed in biphenyl ether to attain the respective subs

Synthesis of certain tetrahydroacridine derivatives of anticipated medicinal value

This study aims at the synthesis and evaluation of the chemotherapeutic activity of a number of 9-substituted tetrahydroacridine derivatives. The starting material, acridine hydrazide, could be prepared through the interaction between cyclohexanone and anthranilic acid, then chlorination of the product, then condensation of the last compound with hydrazine hydrate. The structures of the new compounds were established by IR, 1H NMR, MS spectra, and elemental analysis in certain cases. Antitumor activities as a trial to obtain more effective and less toxic agents were evaluated. The antitumor activity results indicated that the selected tetrahydroacridine derivatives showed antitumor activity against the liver cancer (HEPG2) tumor cell line tested, but with varying intensities in comparison to the known anticancer drugs, 5-fluorouracil and doxorubicin. It was found that compound VIb was the most active and induced a marked growth inhibition (0.694 μg/ml concentration) in a dose-dependent manner against liver cancer (HEPG2), while compound XVIIIa was second in regards to the growth inhibition activity (2.97 μg/ml concentration).

In vitro investigating of anticancer activity of new 7-MEOTA-tacrine heterodimers

A combination of biochemical, biophysical and biological techniques was used to study calf thymus DNA interaction with newly synthesized 7-MEOTA-tacrine thiourea 12–17 and urea heterodimers 18–22, and to measure interference with type I and II topoisomerases. Their biological profile was also inspected in vitro on the HL-60 cell line using different flow cytometric techniques (cell cycle distribution, detection of mitochondrial membrane potential dissipation, and analysis of metabolic activity/viability). The compounds exhibited a profound inhibitory effect on topoisomerase activity (e.g. compound 22 inhibited type I topoisomerase at 1 μM concentration). The treatment of HL-60 cells with the studied compounds showed inhibition of cell growth especially with hybrids containing thiourea (14–17) and urea moieties (21 and 22). Moreover, treatment of human dermal fibroblasts with the studied compounds did not indicate significant cytotoxicity. The observed results suggest beneficial selectivity of the heterodimers as potential drugs to target cancer cells.

The Vilsmeier-Haack formylation of 2,3-dihydro-4H-1,3-benzoxazin-4-ones and isomeric 1,2-dihydro-4H-3,1-benzoxazin-4-ones: An effective approach to functionalized 2H-/4H-chromenes and tetrahydroacridines

We found that 1,3- and isomeric 3,1-benzoxazin-4-ones react with the Vilsmeier reagent in vastly different ways. Thus, either 2H- or 4H-chromenes were obtained in good yields when 1,3-benzoxazin-4-ones were reacted at 75-80 °C, while the formylation of 3,1-benzoxazines at ambient temperature leads to acridine-9-one or 9-chloroacridine derivatives, depending on the amount of Vilsmeier reagent and the nature of substrate.

Gardenamide A-tacrine diad compound as well as preparation method and application thereof

The invention belongs to the field of pharmaceutical chemistry, and discloses a gardenamide A-tacrine diad compound as well as a preparation method and application thereof. The structural formula of the compound is shown as formula I. The compound is prepared through the following steps: (1) genipin is adopted as a raw material I and hemiacetal at the C-1 position of genipin is converted into lactone firstly, lactone is converted into lactam secondly, and hydroxyl at the C-10 position is oxidized into aldehyde finally, thereby obtaining an intermediate compound DG; (2) methyl anthranilate is adopted as a raw material II and chloro tacrine is prepared through hydrolysis and cyclization reactions firstly, and an intermediate compound TN-n is prepared through a nucleophilic substitution reaction between chloro tacrine and corresponding diamine secondly; and (3) the target compound is obtained through an amination-reduction reaction between the prepared intermediate compound DG and intermediate compound TN-n. The compound disclosed by the invention is reported for the first time, has a treating effect on neurodegenerative diseases, and can be applied to preparation of a drug for treating the neurodegenerative diseases.

Novel tacrine-ebselen hybrids with improved cholinesterase inhibitory, hydrogen peroxide and peroxynitrite scavenging activity

A series of tacrine-ebselen hybrids were synthesised and evaluated as possible multifunctional anti-Alzheimer's disease (AD) agents. Compound 6i, which is tacrine linked with 5,6-dimethoxybenzo[d][1,2]selenazol-3(2H)-one by a six-carbon spacer, was the most potent acetylcholinesterase (AChE) and butylcholinesterase (BuChE) inhibitor, with IC50 values of 2.55 and 2.80 nM, respectively. Furthermore, this compound demonstrated similar hydrogen peroxide and peroxynitrite scavenging activity as ebselen by horseradish peroxidase assay and peroxynitrite scavenging activity assay, indicating that this hybrid is a good multifunctional drug candidate for the treatment of AD.

ACRIDINES AS INHIBITORS OF HASPIN AND DYRK KINASES

The present disclosure is directed to compounds of Formula I: which are inhibitors of Haspin kinase and DYRK kinases. The compounds of the present disclosure, and compositions thereof, are useful in the treatment of disease related to Haspin kinase and DY

The novel reaction of ketones with o-oxazoline-substituted anilines

A variety of ketones react with o-oxazoline-substituted anilines in the presence of catalytic amount of p-toluenesulfonic acid in dry n-butanol to form 4-amino-substituted quinolines or 4-quinolones in fair to good yields.

A modified Niementowski reaction for the synthesis of 4-hydroxyquinoline and its realted compounds

The iminoketene generated from anthranilic acid and thionyl chloride reacted with ketones to afford 4-hydroxyquinoline derivatives in good yields.