104675-23-2

Usage

Structure

Benzene derivative with a carbonitrile functional group and an amino group attached to a cyclohexene ring

Usage

Organic synthesis and medicinal chemistry research, development of pharmaceutical drugs, creation of various organic compounds through chemical reactions and modifications

Value in research

Unique structure and properties make it a valuable tool for studying the reactivity and behavior of different chemical compounds in laboratory settings.

InChI:InChI=1/C13H12N2O/c14-9-10-4-1-2-7-13(10)15-11-5-3-6-12(16)8-11/h1-2,4,7-8,15H,3,5-6H2

Upstream product

• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 504-02-9 1,3-cylohexanedione 
• 1885-29-6 anthranilic acid nitrile 

Downstream Products

• 104586-90-5 9-[4,4-bis(4-fluorophenyl)butylamino]-3,4-Dihydroacridin-1(2H)-one 
• 104628-42-4 9-[4,4-bis(4-fluorophenyl)butylamino]-1,2,3,4-tetrahydroacridin-1-ol 
• 104586-88-1 9-[4,4-bis(3-fluorophenyl)butylamino]-3,4-dihydroacridin-1(2H)-one 
• 104603-93-2 3,4-dihydro-9-[(2,3,4,5,6-pentafluorobenzyl)amino]acridin-1(2h)-one 
• 104648-39-7 9-(4,4-Diphenylbutylamino)-1,2,3,4-tetrahydroacridin-1-ol 
• 104675-45-8 3,4-dihydro-9-(4,4-diphenylbutylamino)acridin-1(2H)-one 
• 104628-34-4 1,2,3,4-tetrahydro-9-(2-trifluoromethylbenzyl)aminoacridin-1-ol 
• 104628-36-6 1,2,3,4-tetrahydro-9-(3-trifluoromethylbenzylamino)acridin-1-ol 
• 104586-82-5 3,4-Dihydro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one 
• 104628-37-7 1,2,3,4-tetrahydro-9-(4-trifluoromethylbenzylamino)acridin-1-ol 
• 104586-84-7 3,4-Dihydro-9-(3-trifluoromethylbenzylamino)acridin-1(2H)-one 
• 104586-85-8 3,4-Dihydro-9-(4-trifluoromethylbenzylamino)acridin-1(2H)-one 
• 104628-43-5 9-(3-phenoxypropylamino)-1,2,3,4-tetrahydroacridin-1-ol 
• 104586-92-7 3,4-Dihydro-9-(3-phenoxypropylamino)acridin-1(2H)-one 

Relevant academic research and scientific papers

Synthesis of enaminones in aqueous media using catalytic dilute HCl

(Chemical Equation Presented) A green and convenient approach to the synthesis of β-enaminones from aromatic amines and 5-substituted-1,3- cyclohexanedione in the presence of dilute hydrochloric acid (30 mmol=L) as a catalyst in solvent-free media is described. This method provides several advantages such as environmental friendliness, low cost, good yields, and simple workup procedure. Copyright Taylor & Francis Group, LLC.

Synthesis and biological testing of pyrano[2,3-a]acridinones

The synthesis of 12-amino-7a and 12-hydroxy-2-arylpyrano[2,3-a]acridin-4-ones 7b and 19 via the von Strandtmann flavone annelation procedure is described, in which the pyranone ring is formed by the reaction of a β-ketosulfoxide 13, 18 with an aromatic aldehyde.

Preparation of enamines in aqueous media

The synthesis of enamines in aqueous media and a process for the preparation of memory enhancing 9-amino-1,2,3,4-tetrahydracridines are described.

Method of reducing a carbonyl containing acridine

A method of reducing a carbonyl containing acridine of the formula STR1 where n is 1, 2 or 3; X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, trifluoromethyl, or NR3 R4 where R3 and R4 are independently hydrogen or loweralkyl; R is hydrogen or loweralkyl and R1 is hydrogen, loweralkyl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, furylloweralkyl, thienylloweralkyl, oxygen-bridged arylloweralkyl, oxygen-bridged diarylloweralkyl, oxygen-bridged furylloweralkyl or oxygen-bridged thienylloweralkyl, is disclosed.

9-Amino-1,2,3,4-tetrahydroacridin-1-ols: Synthesis and evaluation as potential Alzheimer's disease therapeutics

The synthesis of a series of 9-amino-1,2,3,4-tetrahydroacridin-1-ols is reported. These compounds are related to 1,2,3,4-tetrahydro-9-acridinamine (THA, tacrine). They inhibit acetylcholinesterase in vitro and are active in a model that may be predictive of activity in Alzheimer's disease - the scopolamine-induced impairment of 24-h memory of a passive dark-avoidance paradigm in mice. Two compounds, (±)-9-amino-1,2,3,4-tetrahydroacridin-1-ol maleate (1a, HP-029) and (±)-9-(benzylamino)-1,2,3,4-tetrahydroacridin-1-ol maleate (1p, HP-128), were also active in reversing the deficit in 72-h retention of a one-trial dark-avoidance task in rats, induced by ibotenic acid lesions in the nucleus basalis magnocellularis. In addition, compound 1p showed potent in vitro inhibition of the uptake of radiolabeled noradrenaline and dopamine (IC50 = 0.070 and 0.30 μM, respectively). Compounds 1a and 1p, which showed less acute toxicity in both rats and mice than THA, are in phase II and phase I clinical trials, respectively, for Alzheimer's disease.

9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds

There are disclosed compounds having the formula STR1 wherein n is 1, 2 or 3; X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, NHCOR2 where R2 is loweralkyl, or NR3 R4 where R3 and R4 are independently hydrogen or loweralkyl; R is hydrogen or loweralkyl; R1 is hydrogen, loweralkyl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, furylloweralkyl, thienylloweralkyl, oxygen-bridged arylloweralkyl, oxygen-bridged diarylloweralkyl, oxygen-bridged furylloweralkyl or oxygen-bridged thienylloweralkyl; Y is C=O or CR5 OH where R5 is hydrogen or loweralkyl; Z is CH2 or C=CR6 R7 where R6 and R7 are independently hydrogen or loweralkyl; or Y and Z taken together is CR5 =CH where CR5 and CH correspond to Y and Z respectively; an optical antipode thereof, or a pharmaceutically acceptable acid addition salt thereof, which are useful for enhancing memory, methods for synthesizing them, and pharmaceutical compositions comprising an effective memory enhancing amount of such a compound.

9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds

There are disclosed compounds having the formula STR1 wherein X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, NHCOR2 wherein R2 is loweralkyl, or a group of the formula NR3 R4 wherein R3/s