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3. (-)-phenethylcymserine

(-)-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)

1. Recent progress in the identification of selective butyrylcholinesterase inhibitors for Alzheimer's disease

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

Abstract : Li_2017_Eur.J.Med.Chem_132_294

ESTHER : Li_2017_Eur.J.Med.Chem_132_294

PubMedSearch : Li_2017_Eur.J.Med.Chem_132_294

PubMedID: 28371641

2. Inhibition of human carboxylesterases hCE1 and hiCE by cholinesterase inhibitors

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

Abstract : Tsurkan_2013_Chem.Biol.Interact_203_226

ESTHER : Tsurkan_2013_Chem.Biol.Interact_203_226

PubMedSearch : Tsurkan_2013_Chem.Biol.Interact_203_226

PubMedID: 23123248

3. Acetylcholinesterase deficiency contributes to neuromuscular junction dysfunction in type 1 diabetic neuropathy

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

Abstract : Garcia_2012_Am.J.Physiol.Endocrinol.Metab_303_E551

ESTHER : Garcia_2012_Am.J.Physiol.Endocrinol.Metab_303_E551

PubMedSearch : Garcia_2012_Am.J.Physiol.Endocrinol.Metab_303_E551

PubMedID: 22739110

4. Quinolizidinyl derivatives of bi- and tricyclic systems as potent inhibitors of acetyl- and butyrylcholinesterase with potential in Alzheimer's disease

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

Abstract : Tasso_2011_Eur.J.Med.Chem_46_2170

ESTHER : Tasso_2011_Eur.J.Med.Chem_46_2170

PubMedSearch : Tasso_2011_Eur.J.Med.Chem_46_2170

PubMedID: 21459491

5. Long-acting anticholinesterases for myasthenia gravis: synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine

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

Abstract : Yu_2010_Bioorg.Med.Chem_18_4687

ESTHER : Yu_2010_Bioorg.Med.Chem_18_4687

PubMedSearch : Yu_2010_Bioorg.Med.Chem_18_4687

PubMedID: 20627738

6. Design, synthesis, evaluation and QSAR analysis of N(1)-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors

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

Abstract : Takahashi_2010_Bioorg.Med.Chem.Lett_20_1718

ESTHER : Takahashi_2010_Bioorg.Med.Chem.Lett_20_1718

PubMedSearch : Takahashi_2010_Bioorg.Med.Chem.Lett_20_1718

PubMedID: 20137934

7. Synthesis of novel phenserine-based-selective inhibitors of butyrylcholinesterase for Alzheimer's disease

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

Abstract : Yu_1999_J.Med.Chem_42_1855

ESTHER : Yu_1999_J.Med.Chem_42_1855

PubMedSearch : Yu_1999_J.Med.Chem_42_1855

PubMedID: 10346939

Array
(
    [id] => 4503
    [inhibitor] => (-)-phenethylcymserine
    [type] => Array
        (
            [0] => Derivative of physostigmine-eserine
            [1] => Carbamate
        )

    [other_name] => Array
        (
            [0] => Phenethylcymserine
            [1] => CHEMBL1080386
            [2] => BDBM50312803
            [3] => (3aS,8aR)-3a,8-dimethyl-1-phenethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl 4-isopropylphenylcarbamate
            [4] => [(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
            [5] => CHEMBL54577
            [6] => BDBM50077263
            [7] => (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
        )

    [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
    [formula] => C30H35N3O2
    [cas_number] => 
    [mw] => 469.6
    [pick_me_to_call] => display_script
    [kinetic_parameter] => 
    [paper] => Yu_2010_Bioorg.Med.Chem_18_4687 || Garcia_2012_Am.J.Physiol.Endocrinol.Metab_303_E551 || Tsurkan_2013_Chem.Biol.Interact_203_226 || Tasso_2011_Eur.J.Med.Chem_46_2170 || Takahashi_2010_Bioorg.Med.Chem.Lett_20_1718 || Li_2017_Eur.J.Med.Chem_132_294 || Yu_1999_J.Med.Chem_42_1855
    [comment] => IC 50 microM hCE1 20.5 +\/- 10.4\; hCE2 5.6 +\/- 2.7\; hACHE 1.0 +\/- 0.2\; hBChE 0.51 +\/- 0.06
    [gene_locus] => human-CES2 || human-ACHE || human-BCHE
    [kin_inhibitor] => 
    [cid] => 9804733 || 11385845
    [family] => Carb_B_Chordata || BCHE || ACHE
    [inchikey] => WKDFOVDLOVYRAJ-TXDWVUBVSA-N
    [canonicalsmiles] => 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
    [wikipedia] => 
    [iupharlig] => 
    [structure] => 
    [substrate] => 
    [interact_gene_locus] => 
    [mutation] => 
    [comment2] => 
    [extoxnet] => 
    [news] => 
    [theoretical_model] => 
)