7-PhO-THA

7-PhO-THA IC50 hAChE 2.40 +/- 1.8 hBCHE 4.9 +/- 3.3 microM, inhibits the GluN1/GluN2B subtype of NMDARs via an ifenprodil-binding site. hBCHE(60mV) 1.7 +/- 0.1 microM

General

Type : Multitarget, NMDA-Ligand, Derivative of Tacrine

Chemical_Nomenclature : 7-(phenoxy)-1,2,3,4-tetrahydroacridin-9-amine

Canonical SMILES : C1(=CC=C2C(=C1)C(=C3C(=N2)CCCC3)N)OC4=CC=CC=C4

InChI : InChI=1S\/C19H18N2O\/c20-19-15-8-4-5-9-17(15)21-18-11-10-14(12-16(18)19)22-13-6-2-1-3-7-13\/h1-3,6-7,10-12H,4-5,8-9H2,(H2,20,21)

InChIKey : RFKHKOZYFWZDAJ-UHFFFAOYSA-N

Other name(s) : 7-phenoxytacrine


MW : 290.36

Formula : C19H18N2O

CAS_number :

PubChem :

UniChem : RFKHKOZYFWZDAJ-UHFFFAOYSA-N

Target

Families : 7-PhO-THA ligand of proteins in family
ACHE BCHE

Protein :
human-ACHE human-BCHE

References (5)

Title : Phenoxytacrine derivatives: Low-toxicity neuroprotectants exerting affinity to ifenprodil-binding site and cholinesterase inhibition - Misiachna_2024_Eur.J.Med.Chem_266_116130
Author(s) : Misiachna A , Svobodova B , Netolicky J , Chvojkova M , Kleteckova L , Prchal L , Novak M , Hrabinova M , Kucera T , Muckova L , Moravcova Z , Karasova JZ , Pejchal J , Blazek F , Malinak D , Hakenova K , Krausova BH , Kolcheva M , Ladislav M , Korabecny J , Pahnke J , Vales K , Horak M , Soukup O
Ref : Eur Journal of Medicinal Chemistry , 266 :116130 , 2024
Abstract :
PubMedSearch : Misiachna_2024_Eur.J.Med.Chem_266_116130
PubMedID: 38218127

Title : Tacrine First-Phase Biotransformation and Associated Hepatotoxicity: A Possible Way to Avoid Quinone Methide Formation - Novak_2023_ACS.Chem.Biol_18_1993
Author(s) : Novak M , Vajrychova M , Koutsilieri S , Sismanoglou DC , Kobrlova T , Prchal L , Svobodova B , Korabecny J , Zarybnicky T , Raisova-Stuchlikova L , Skalova L , Lauschke VM , Kucera R , Soukup O
Ref : ACS Chemical Biology , 18 :1993 , 2023
Abstract :
PubMedSearch : Novak_2023_ACS.Chem.Biol_18_1993
PubMedID: 37622522

Title : UHPLC-Orbitrap study of the first phase tacrine in vitro metabolites and related Alzheimer's drug candidates using human liver microsomes - Novak_2023_J.Pharm.Biomed.Anal_224_115154
Author(s) : Novak M , Svobodova B , Konecny J , Kuratkova A , Nevosadova L , Prchal L , Korabecny J , Lauschke VM , Soukup O , Kucera R
Ref : J Pharm Biomed Anal , 224 :115154 , 2023
Abstract :
PubMedSearch : Novak_2023_J.Pharm.Biomed.Anal_224_115154
PubMedID: 36442458

Title : 7-phenoxytacrine is a dually acting drug with neuroprotective efficacy in vivo - Kaniakova_2021_Biochem.Pharmacol__114460
Author(s) : Kaniakova M , Korabecny J , Holubova K , Kleteckova L , Chvojkova M , Hakenova K , Prchal L , Novak M , Dolezal R , Hepnarova V , Svobodova B , Kucera T , Lichnerova K , Krausova B , Horak M , Vales K , Soukup O
Ref : Biochemical Pharmacology , :114460 , 2021
Abstract :
PubMedSearch : Kaniakova_2021_Biochem.Pharmacol__114460
PubMedID: 33571502

Title : The Evaluation of Benefit of Newly Prepared Reversible Inhibitors of Acetylcholinesterase and Commonly Used Pyridostigmine as Pharmacological Pretreatment of Soman-Poisoned Mice - Kassa_2017_Acta.Medica.(Hradec.Kralove)_60_37
Author(s) : Kassa J , Korabecny J , Nepovimova E
Ref : Acta Medica (Hradec Kralove) , 60 :37 , 2017
Abstract :
PubMedSearch : Kassa_2017_Acta.Medica.(Hradec.Kralove)_60_37
PubMedID: 28418831