(-)-phenethylcymserine

IC 50 microM hCE1 20.5 +/- 10.4; hCE2 5.6 +/- 2.7; hACHE 1.0 +/- 0.2; hBChE 0.51 +/- 0.06

General

Type : Derivative of physostigmine-eserine, Carbamate

Chemical_Nomenclature : [(8bS)-4,8b-dimethyl-3-(2-phenylethyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-(4-propan-2-ylphenyl)carbamate

Canonical SMILES : CC(C)C1=CC=C(C=C1)NC(=O)OC2=CC3=C(C=C2)N(C4C3(CCN4CCC5=CC=CC=C5)C)C

InChI : InChI=1S\/C30H35N3O2\/c1-21(2)23-10-12-24(13-11-23)31-29(34)35-25-14-15-27-26(20-25)30(3)17-19-33(28(30)32(27)4)18-16-22-8-6-5-7-9-22\/h5-15,20-21,28H,16-19H2,1-4H3,(H,31,34)\/t28?,30-\/m0\/s1

InChIKey : WKDFOVDLOVYRAJ-TXDWVUBVSA-N

Other name(s) : Phenethylcymserine, CHEMBL1080386, BDBM50312803, (3aS,8aR)-3a,8-dimethyl-1-phenethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl 4-isopropylphenylcarbamate, [(3aR,8bS)-4,8b-dimethyl-3-(2-phenylethyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-(4-propan-2-ylphenyl)carbamate, CHEMBL54577, BDBM50077263, (4-Isopropyl-phenyl)-carbamic acid (S)-3a,8-dimethyl-1-phenethyl-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indol-5-yl ester


MW : 469.6

Formula : C30H35N3O2

CAS_number :

PubChem : 9804733, 11385845

UniChem : WKDFOVDLOVYRAJ-TXDWVUBVSA-N

Target

Families : (-)-phenethylcymserine ligand of proteins in family
Carb_B_Chordata BCHE ACHE

Protein :
human-CES2 human-ACHE human-BCHE

References (7)

Title : Recent progress in the identification of selective butyrylcholinesterase inhibitors for Alzheimer's disease - Li_2017_Eur.J.Med.Chem_132_294
Author(s) : Li Q , Yang H , Chen Y , Sun H
Ref : Eur Journal of Medicinal Chemistry , 132 :294 , 2017
PubMedID: 28371641

Title : Inhibition of human carboxylesterases hCE1 and hiCE by cholinesterase inhibitors - Tsurkan_2013_Chem.Biol.Interact_203_226
Author(s) : Tsurkan LG , Hatfield MJ , Edwards CC , Hyatt JL , Potter PM
Ref : Chemico-Biological Interactions , 203 :226 , 2013
PubMedID: 23123248

Title : Acetylcholinesterase deficiency contributes to neuromuscular junction dysfunction in type 1 diabetic neuropathy - Garcia_2012_Am.J.Physiol.Endocrinol.Metab_303_E551
Author(s) : Garcia CC , Potian JG , Hognason K , Thyagarajan B , Sultatos LG , Souayah N , Routh VH , McArdle JJ
Ref : American Journal of Physiology Endocrinol Metab , 303 :E551 , 2012
PubMedID: 22739110

Title : Quinolizidinyl derivatives of bi- and tricyclic systems as potent inhibitors of acetyl- and butyrylcholinesterase with potential in Alzheimer's disease - Tasso_2011_Eur.J.Med.Chem_46_2170
Author(s) : Tasso B , Catto M , Nicolotti O , Novelli F , Tonelli M , Giangreco I , Pisani L , Sparatore A , Boido V , Carotti A , Sparatore F
Ref : Eur Journal of Medicinal Chemistry , 46 :2170 , 2011
PubMedID: 21459491

Title : Long-acting anticholinesterases for myasthenia gravis: synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine - Yu_2010_Bioorg.Med.Chem_18_4687
Author(s) : Yu QS , Holloway HW , Luo W , Lahiri DK , Brossi A , Greig NH
Ref : Bioorganic & Medicinal Chemistry , 18 :4687 , 2010
PubMedID: 20627738

Title : Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors - Takahashi_2010_Bioorg.Med.Chem.Lett_20_1718
Author(s) : Takahashi J , Hijikuro I , Kihara T , Murugesh MG , Fuse S , Kunimoto R , Tsumura Y , Akaike A , Niidome T , Okuno Y , Takahashi T , Sugimoto H
Ref : Bioorganic & Medicinal Chemistry Lett , 20 :1718 , 2010
PubMedID: 20137934

Title : Synthesis of novel phenserine-based-selective inhibitors of butyrylcholinesterase for Alzheimer's disease - Yu_1999_J.Med.Chem_42_1855
Author(s) : Yu Q , Holloway HW , Utsuki T , Brossi A , Greig NH
Ref : Journal of Medicinal Chemistry , 42 :1855 , 1999
PubMedID: 10346939