HuprineY
General
Type : Derivative of Huperzine, Organochlorine
Chemical_Nomenclature : 7-chloro-15-methyl-10-azatetracyclo[11.3.1.02,11.04,9]heptadeca-2,4(9),5,7,10,14-hexaen-3-amine
Canonical SMILES : CC1=CC2CC(C1)C3=C(C4=C(C=C(C=C4)Cl)N=C3C2)N
InChI : InChI=1S\/C17H17ClN2\/c1-9-4-10-6-11(5-9)16-15(7-10)20-14-8-12(18)2-3-13(14)17(16)19\/h2-4,8,10-11H,5-7H2,1H3,(H2,19,20)
InChIKey : UKCBMHDZLYYTMI-UHFFFAOYSA-N
Other name(s) : Huprine Y || CHEMBL140476 || CHEMBL536047 || rac-huprine H3 || Huprine Y.HCl || (+\/-)-huprine Y-HCl || (+\/-)-huprineY hydrochloride || BDBM10592
MW : 284.8
Formula : C17H17ClN2
CAS_number :
PubChem : 10107976
UniChem : UKCBMHDZLYYTMI-UHFFFAOYSA-N
Target
References (36)
| Title : Huprine Y - tryptophan heterodimers with potential implication to Alzheimer's disease treatment - Mezeiova_2021_Bioorg.Med.Chem.Lett__128100 |
| Author(s) : Mezeiova E , Hrabinova M , Hepnarova V , Jun D , Janockova J , Muckova L , Prchal L , Kristofikova Z , Kucera T , Gorecki L , Chalupova K , Kunes J , Hroudova J , Soukup O , Korabecny J |
| Ref : Bioorganic & Medicinal Chemistry Lett , :128100 , 2021 |
| Abstract : |
| PubMedSearch : Mezeiova_2021_Bioorg.Med.Chem.Lett__128100 |
| PubMedID: 33984470 |
| Title : Huprine Y - tryptophan heterodimers with potential implication to Alzheimer's disease treatment - Mezeiova_2021_Bioorg.Med.Chem.Lett__128100 |
| Author(s) : Mezeiova E , Hrabinova M , Hepnarova V , Jun D , Janockova J , Muckova L , Prchal L , Kristofikova Z , Kucera T , Gorecki L , Chalupova K , Kunes J , Hroudova J , Soukup O , Korabecny J |
| Ref : Bioorganic & Medicinal Chemistry Lett , :128100 , 2021 |
| Abstract : |
| PubMedSearch : Mezeiova_2021_Bioorg.Med.Chem.Lett__128100 |
| PubMedID: 33984470 |
| Title : Huprine Y - tryptophan heterodimers with potential implication to Alzheimer's disease treatment - Mezeiova_2021_Bioorg.Med.Chem.Lett__128100 |
| Author(s) : Mezeiova E , Hrabinova M , Hepnarova V , Jun D , Janockova J , Muckova L , Prchal L , Kristofikova Z , Kucera T , Gorecki L , Chalupova K , Kunes J , Hroudova J , Soukup O , Korabecny J |
| Ref : Bioorganic & Medicinal Chemistry Lett , :128100 , 2021 |
| Abstract : |
| PubMedSearch : Mezeiova_2021_Bioorg.Med.Chem.Lett__128100 |
| PubMedID: 33984470 |
| Title : Increasing Polarity in Tacrine and Huprine Derivatives: Potent Anticholinesterase Agents for the Treatment of Myasthenia Gravis - Galdeano_2018_Molecules_23_ |
| Author(s) : Galdeano C , Coquelle N , Cieslikiewicz-Bouet M , Bartolini M , Perez B , Clos MV , Silman I , Jean L , Colletier JP , Renard PY , Munoz-Torrero D |
| Ref : Molecules , 23 : , 2018 |
| Abstract : |
| PubMedSearch : Galdeano_2018_Molecules_23_ |
| PubMedID: 29534488 |
| Gene_locus related to this paper: torca-ACHE |
| Title : Increasing Polarity in Tacrine and Huprine Derivatives: Potent Anticholinesterase Agents for the Treatment of Myasthenia Gravis - Galdeano_2018_Molecules_23_ |
| Author(s) : Galdeano C , Coquelle N , Cieslikiewicz-Bouet M , Bartolini M , Perez B , Clos MV , Silman I , Jean L , Colletier JP , Renard PY , Munoz-Torrero D |
| Ref : Molecules , 23 : , 2018 |
| Abstract : |
| PubMedSearch : Galdeano_2018_Molecules_23_ |
| PubMedID: 29534488 |
| Gene_locus related to this paper: torca-ACHE |
| Title : Increasing Polarity in Tacrine and Huprine Derivatives: Potent Anticholinesterase Agents for the Treatment of Myasthenia Gravis - Galdeano_2018_Molecules_23_ |
| Author(s) : Galdeano C , Coquelle N , Cieslikiewicz-Bouet M , Bartolini M , Perez B , Clos MV , Silman I , Jean L , Colletier JP , Renard PY , Munoz-Torrero D |
| Ref : Molecules , 23 : , 2018 |
| Abstract : |
| PubMedSearch : Galdeano_2018_Molecules_23_ |
| PubMedID: 29534488 |
| Gene_locus related to this paper: torca-ACHE |
| Title : Synthesis and antiprotozoal activity of oligomethylene- and p-phenylene-bis(methylene)-linked bis(+)-huprines - Sola_2014_Bioorg.Med.Chem.Lett_24_5435 |
| Author(s) : Sola I , Artigas A , Taylor MC , Gbedema SY , Perez B , Clos MV , Wright CW , Kelly JM , Munoz-Torrero D |
| Ref : Bioorganic & Medicinal Chemistry Lett , 24 :5435 , 2014 |
| Abstract : |
| PubMedSearch : Sola_2014_Bioorg.Med.Chem.Lett_24_5435 |
| PubMedID: 25454267 |
| Title : Shogaol-huprine hybrids: Dual antioxidant and anticholinesterase agents with beta-amyloid and tau anti-aggregating properties - Perez-Areales_2014_Bioorg.Med.Chem_22_5298 |
| Author(s) : Perez-Areales FJ , Di Pietro O , Espargaro A , Vallverdu-Queralt A , Galdeano C , Ragusa IM , Viayna E , Guillou C , Clos MV , Perez B , Sabate R , Lamuela-Raventos RM , Luque FJ , Munoz-Torrero D |
| Ref : Bioorganic & Medicinal Chemistry , 22 :5298 , 2014 |
| Abstract : |
| PubMedSearch : Perez-Areales_2014_Bioorg.Med.Chem_22_5298 |
| PubMedID: 25156301 |
| Title : Synthesis and antiprotozoal activity of oligomethylene- and p-phenylene-bis(methylene)-linked bis(+)-huprines - Sola_2014_Bioorg.Med.Chem.Lett_24_5435 |
| Author(s) : Sola I , Artigas A , Taylor MC , Gbedema SY , Perez B , Clos MV , Wright CW , Kelly JM , Munoz-Torrero D |
| Ref : Bioorganic & Medicinal Chemistry Lett , 24 :5435 , 2014 |
| Abstract : |
| PubMedSearch : Sola_2014_Bioorg.Med.Chem.Lett_24_5435 |
| PubMedID: 25454267 |
| Title : Shogaol-huprine hybrids: Dual antioxidant and anticholinesterase agents with beta-amyloid and tau anti-aggregating properties - Perez-Areales_2014_Bioorg.Med.Chem_22_5298 |
| Author(s) : Perez-Areales FJ , Di Pietro O , Espargaro A , Vallverdu-Queralt A , Galdeano C , Ragusa IM , Viayna E , Guillou C , Clos MV , Perez B , Sabate R , Lamuela-Raventos RM , Luque FJ , Munoz-Torrero D |
| Ref : Bioorganic & Medicinal Chemistry , 22 :5298 , 2014 |
| Abstract : |
| PubMedSearch : Perez-Areales_2014_Bioorg.Med.Chem_22_5298 |
| PubMedID: 25156301 |
| Title : Synthesis and antiprotozoal activity of oligomethylene- and p-phenylene-bis(methylene)-linked bis(+)-huprines - Sola_2014_Bioorg.Med.Chem.Lett_24_5435 |
| Author(s) : Sola I , Artigas A , Taylor MC , Gbedema SY , Perez B , Clos MV , Wright CW , Kelly JM , Munoz-Torrero D |
| Ref : Bioorganic & Medicinal Chemistry Lett , 24 :5435 , 2014 |
| Abstract : |
| PubMedSearch : Sola_2014_Bioorg.Med.Chem.Lett_24_5435 |
| PubMedID: 25454267 |
| Title : Shogaol-huprine hybrids: Dual antioxidant and anticholinesterase agents with beta-amyloid and tau anti-aggregating properties - Perez-Areales_2014_Bioorg.Med.Chem_22_5298 |
| Author(s) : Perez-Areales FJ , Di Pietro O , Espargaro A , Vallverdu-Queralt A , Galdeano C , Ragusa IM , Viayna E , Guillou C , Clos MV , Perez B , Sabate R , Lamuela-Raventos RM , Luque FJ , Munoz-Torrero D |
| Ref : Bioorganic & Medicinal Chemistry , 22 :5298 , 2014 |
| Abstract : |
| PubMedSearch : Perez-Areales_2014_Bioorg.Med.Chem_22_5298 |
| PubMedID: 25156301 |
| Title : Effects of (+\/-)-huprine Y and (+\/-)-huprine Z, two new anticholinesterasic drugs, on muscarinic receptors - Alcala_2005_Neurosci.Lett_379_106 |
| Author(s) : Alcala MM , Maderuelo A , Vivas NM , Camps P , Munoz-Torrero D , Clos MV , Badia A |
| Ref : Neuroscience Letters , 379 :106 , 2005 |
| Abstract : |
| PubMedSearch : Alcala_2005_Neurosci.Lett_379_106 |
| PubMedID: 15823425 |
| Title : Synthesis and pharmacological evaluation of huprine-tacrine heterodimers: subnanomolar dual binding site acetylcholinesterase inhibitors - Camps_2005_J.Med.Chem_48_1701 |
| Author(s) : Camps P , Formosa X , Munoz-Torrero D , Petrignet J , Badia A , Clos MV |
| Ref : Journal of Medicinal Chemistry , 48 :1701 , 2005 |
| Abstract : |
| PubMedSearch : Camps_2005_J.Med.Chem_48_1701 |
| PubMedID: 15771413 |
| Title : Effects of (+\/-)-huprine Y and (+\/-)-huprine Z, two new anticholinesterasic drugs, on muscarinic receptors - Alcala_2005_Neurosci.Lett_379_106 |
| Author(s) : Alcala MM , Maderuelo A , Vivas NM , Camps P , Munoz-Torrero D , Clos MV , Badia A |
| Ref : Neuroscience Letters , 379 :106 , 2005 |
| Abstract : |
| PubMedSearch : Alcala_2005_Neurosci.Lett_379_106 |
| PubMedID: 15823425 |
| Title : Synthesis and pharmacological evaluation of huprine-tacrine heterodimers: subnanomolar dual binding site acetylcholinesterase inhibitors - Camps_2005_J.Med.Chem_48_1701 |
| Author(s) : Camps P , Formosa X , Munoz-Torrero D , Petrignet J , Badia A , Clos MV |
| Ref : Journal of Medicinal Chemistry , 48 :1701 , 2005 |
| Abstract : |
| PubMedSearch : Camps_2005_J.Med.Chem_48_1701 |
| PubMedID: 15771413 |
| Title : Effects of (+\/-)-huprine Y and (+\/-)-huprine Z, two new anticholinesterasic drugs, on muscarinic receptors - Alcala_2005_Neurosci.Lett_379_106 |
| Author(s) : Alcala MM , Maderuelo A , Vivas NM , Camps P , Munoz-Torrero D , Clos MV , Badia A |
| Ref : Neuroscience Letters , 379 :106 , 2005 |
| Abstract : |
| PubMedSearch : Alcala_2005_Neurosci.Lett_379_106 |
| PubMedID: 15823425 |
| Title : Synthesis and pharmacological evaluation of huprine-tacrine heterodimers: subnanomolar dual binding site acetylcholinesterase inhibitors - Camps_2005_J.Med.Chem_48_1701 |
| Author(s) : Camps P , Formosa X , Munoz-Torrero D , Petrignet J , Badia A , Clos MV |
| Ref : Journal of Medicinal Chemistry , 48 :1701 , 2005 |
| Abstract : |
| PubMedSearch : Camps_2005_J.Med.Chem_48_1701 |
| PubMedID: 15771413 |
| Title : (+\/-)-huprine Y, (-)-huperzine A and tacrine do not show neuroprotective properties in an apoptotic model of neuronal cytoskeletal alteration - Jorda_2004_J.Alzheimers.Dis_6_577 |
| Author(s) : Jorda EG , Verdaguer E , Jimenez A , Canudas AM , Rimbau V , Camps P , Munoz-Torrero D , Camins A , Pallas M |
| Ref : J Alzheimers Dis , 6 :577 , 2004 |
| Abstract : |
| PubMedSearch : Jorda_2004_J.Alzheimers.Dis_6_577 |
| PubMedID: 15665397 |
| Title : Modulation of binding strength in several classes of active site inhibitors of acetylcholinesterase studied by comparative binding energy analysis - Martin-Santamaria_2004_J.Med.Chem_47_4471 |
| Author(s) : Martin-Santamaria S , Munoz-Muriedas J , Luque FJ , Gago F |
| Ref : Journal of Medicinal Chemistry , 47 :4471 , 2004 |
| Abstract : |
| PubMedSearch : Martin-Santamaria_2004_J.Med.Chem_47_4471 |
| PubMedID: 15317459 |
| Title : (+\/-)-huprine Y, (-)-huperzine A and tacrine do not show neuroprotective properties in an apoptotic model of neuronal cytoskeletal alteration - Jorda_2004_J.Alzheimers.Dis_6_577 |
| Author(s) : Jorda EG , Verdaguer E , Jimenez A , Canudas AM , Rimbau V , Camps P , Munoz-Torrero D , Camins A , Pallas M |
| Ref : J Alzheimers Dis , 6 :577 , 2004 |
| Abstract : |
| PubMedSearch : Jorda_2004_J.Alzheimers.Dis_6_577 |
| PubMedID: 15665397 |
| Title : Modulation of binding strength in several classes of active site inhibitors of acetylcholinesterase studied by comparative binding energy analysis - Martin-Santamaria_2004_J.Med.Chem_47_4471 |
| Author(s) : Martin-Santamaria S , Munoz-Muriedas J , Luque FJ , Gago F |
| Ref : Journal of Medicinal Chemistry , 47 :4471 , 2004 |
| Abstract : |
| PubMedSearch : Martin-Santamaria_2004_J.Med.Chem_47_4471 |
| PubMedID: 15317459 |
| Title : (+\/-)-huprine Y, (-)-huperzine A and tacrine do not show neuroprotective properties in an apoptotic model of neuronal cytoskeletal alteration - Jorda_2004_J.Alzheimers.Dis_6_577 |
| Author(s) : Jorda EG , Verdaguer E , Jimenez A , Canudas AM , Rimbau V , Camps P , Munoz-Torrero D , Camins A , Pallas M |
| Ref : J Alzheimers Dis , 6 :577 , 2004 |
| Abstract : |
| PubMedSearch : Jorda_2004_J.Alzheimers.Dis_6_577 |
| PubMedID: 15665397 |
| Title : Modulation of binding strength in several classes of active site inhibitors of acetylcholinesterase studied by comparative binding energy analysis - Martin-Santamaria_2004_J.Med.Chem_47_4471 |
| Author(s) : Martin-Santamaria S , Munoz-Muriedas J , Luque FJ , Gago F |
| Ref : Journal of Medicinal Chemistry , 47 :4471 , 2004 |
| Abstract : |
| PubMedSearch : Martin-Santamaria_2004_J.Med.Chem_47_4471 |
| PubMedID: 15317459 |
| Title : Characterisation of the anticholinesterase activity of two new tacrine-huperzine A hybrids - Alcala_2003_Neuropharmacol_44_749 |
| Author(s) : Alcala Mdel M , Vivas NM , Hospital S , Camps P , Munoz-Torrero D , Badia A |
| Ref : Neuropharmacology , 44 :749 , 2003 |
| Abstract : |
| PubMedSearch : Alcala_2003_Neuropharmacol_44_749 |
| PubMedID: 12681373 |
| Title : Neuroprotective effects of (+\/-)-huprine Y on in vitro and in vivo models of excitoxicity damage - Canudas_2003_Exp.Neurol_180_123 |
| Author(s) : Canudas AM , Pubill D , Sureda FX , Verdaguer E , Camps P , Munoz-Torrero D , Jimenez A , Camins A , Pallas M |
| Ref : Experimental Neurology , 180 :123 , 2003 |
| Abstract : |
| PubMedSearch : Canudas_2003_Exp.Neurol_180_123 |
| PubMedID: 12684026 |
| Title : Characterisation of the anticholinesterase activity of two new tacrine-huperzine A hybrids - Alcala_2003_Neuropharmacol_44_749 |
| Author(s) : Alcala Mdel M , Vivas NM , Hospital S , Camps P , Munoz-Torrero D , Badia A |
| Ref : Neuropharmacology , 44 :749 , 2003 |
| Abstract : |
| PubMedSearch : Alcala_2003_Neuropharmacol_44_749 |
| PubMedID: 12681373 |
| Title : Neuroprotective effects of (+\/-)-huprine Y on in vitro and in vivo models of excitoxicity damage - Canudas_2003_Exp.Neurol_180_123 |
| Author(s) : Canudas AM , Pubill D , Sureda FX , Verdaguer E , Camps P , Munoz-Torrero D , Jimenez A , Camins A , Pallas M |
| Ref : Experimental Neurology , 180 :123 , 2003 |
| Abstract : |
| PubMedSearch : Canudas_2003_Exp.Neurol_180_123 |
| PubMedID: 12684026 |
| Title : Characterisation of the anticholinesterase activity of two new tacrine-huperzine A hybrids - Alcala_2003_Neuropharmacol_44_749 |
| Author(s) : Alcala Mdel M , Vivas NM , Hospital S , Camps P , Munoz-Torrero D , Badia A |
| Ref : Neuropharmacology , 44 :749 , 2003 |
| Abstract : |
| PubMedSearch : Alcala_2003_Neuropharmacol_44_749 |
| PubMedID: 12681373 |
| Title : Neuroprotective effects of (+\/-)-huprine Y on in vitro and in vivo models of excitoxicity damage - Canudas_2003_Exp.Neurol_180_123 |
| Author(s) : Canudas AM , Pubill D , Sureda FX , Verdaguer E , Camps P , Munoz-Torrero D , Jimenez A , Camins A , Pallas M |
| Ref : Experimental Neurology , 180 :123 , 2003 |
| Abstract : |
| PubMedSearch : Canudas_2003_Exp.Neurol_180_123 |
| PubMedID: 12684026 |
| Title : The pharmacology of novel acetylcholinesterase inhibitors, (+\/-)- huprines Y and X, on the Torpedo electric organ - Ros_2001_Eur.J.Pharmacol_421_77 |
| Author(s) : Ros E , Aleu J , Gomez de Aranda I , Munoz-Torrero D , Camps P , Badia A , Marsal J , Solsona C |
| Ref : European Journal of Pharmacology , 421 :77 , 2001 |
| Abstract : |
| PubMedSearch : Ros_2001_Eur.J.Pharmacol_421_77 |
| PubMedID: 11399262 |
| Title : The pharmacology of novel acetylcholinesterase inhibitors, (+\/-)- huprines Y and X, on the Torpedo electric organ - Ros_2001_Eur.J.Pharmacol_421_77 |
| Author(s) : Ros E , Aleu J , Gomez de Aranda I , Munoz-Torrero D , Camps P , Badia A , Marsal J , Solsona C |
| Ref : European Journal of Pharmacology , 421 :77 , 2001 |
| Abstract : |
| PubMedSearch : Ros_2001_Eur.J.Pharmacol_421_77 |
| PubMedID: 11399262 |
| Title : The pharmacology of novel acetylcholinesterase inhibitors, (+\/-)- huprines Y and X, on the Torpedo electric organ - Ros_2001_Eur.J.Pharmacol_421_77 |
| Author(s) : Ros E , Aleu J , Gomez de Aranda I , Munoz-Torrero D , Camps P , Badia A , Marsal J , Solsona C |
| Ref : European Journal of Pharmacology , 421 :77 , 2001 |
| Abstract : |
| PubMedSearch : Ros_2001_Eur.J.Pharmacol_421_77 |
| PubMedID: 11399262 |
| Title : New tacrine-huperzine A hybrids (huprines): highly potent tight-binding acetylcholinesterase inhibitors of interest for the treatment of Alzheimer's disease - Camps_2000_J.Med.Chem_43_4657 |
| Author(s) : Camps P , El Achab R , Morral J , Munoz-Torrero D , Badia A , Banos JE , Vivas NM , Barril X , Orozco M , Luque FJ |
| Ref : Journal of Medicinal Chemistry , 43 :4657 , 2000 |
| Abstract : |
| PubMedSearch : Camps_2000_J.Med.Chem_43_4657 |
| PubMedID: 11101357 |
| Title : New tacrine-huperzine A hybrids (huprines): highly potent tight-binding acetylcholinesterase inhibitors of interest for the treatment of Alzheimer's disease - Camps_2000_J.Med.Chem_43_4657 |
| Author(s) : Camps P , El Achab R , Morral J , Munoz-Torrero D , Badia A , Banos JE , Vivas NM , Barril X , Orozco M , Luque FJ |
| Ref : Journal of Medicinal Chemistry , 43 :4657 , 2000 |
| Abstract : |
| PubMedSearch : Camps_2000_J.Med.Chem_43_4657 |
| PubMedID: 11101357 |
| Title : New tacrine-huperzine A hybrids (huprines): highly potent tight-binding acetylcholinesterase inhibitors of interest for the treatment of Alzheimer's disease - Camps_2000_J.Med.Chem_43_4657 |
| Author(s) : Camps P , El Achab R , Morral J , Munoz-Torrero D , Badia A , Banos JE , Vivas NM , Barril X , Orozco M , Luque FJ |
| Ref : Journal of Medicinal Chemistry , 43 :4657 , 2000 |
| Abstract : |
| PubMedSearch : Camps_2000_J.Med.Chem_43_4657 |
| PubMedID: 11101357 |