6-{2-[4-(4-Fluoro-benzyl)-piperidin-1-yl]-ethanesulfinyl}-3H-benzooxazol-2-one

ID: ALA219631

Chembl Id: CHEMBL219631

Cas Number: 253450-09-8

PubChem CID: 156328

Max Phase: Unknown

Molecular Formula: C21H23FN2O3S

Molecular Weight: 402.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Besonprodil | CI-1041 | CO 200461 | CO-200461 | PD 0196860 | PD-0196860 | Besonprodil|253450-09-8|CI-1041|Besonprodil (USAN)|Besonprodil [USAN]|Co 200461|PD 0196860|6-({2-[4-(4-FLUOROBENZYL)PIPERIDIN-1-YL]ETHYL}SULFINYL)-1,3-BENZOXAZOL-2(3H)-ONE|6-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethylsulfinyl]-3H-1,3-benzoxazol-2-one|5K3N2D15WW|CHEMBL219631|DTXSID2047270|CO-200461|PD-0196860|2(3H)-Benzoxazolone, 6-((2-(4-((4-fluorophenyl)methyl)-1-piperidinyl)ethyl)sulfinyl)|CI 1041; Co 200461; PD 0Show More⌵

Canonical SMILES:  O=c1[nH]c2ccc([S+]([O-])CCN3CCC(Cc4ccc(F)cc4)CC3)cc2o1

Standard InChI:  InChI=1S/C21H23FN2O3S/c22-17-3-1-15(2-4-17)13-16-7-9-24(10-8-16)11-12-28(26)18-5-6-19-20(14-18)27-21(25)23-19/h1-6,14,16H,7-13H2,(H,23,25)

Standard InChI Key:  FCBQJNCAKZSIAH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA219631

   BESONPRODIL

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 402.49

Molecular Weight (Monoisotopic): 402.1413

AlogP: 3.32

#Rotatable Bonds: 6

Polar Surface Area: 72.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.38

CX Basic pKa: 7.86

CX LogP: 2.92

CX LogD: 2.49

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -0.68

References

1. Borza I, Kolok S, Gere A, Agai-Csongor E, Agai B, Tárkányi G, Horváth C, Barta-Szalai G, Bozó E, Kiss C, Bielik A, Nagy J, Farkas S, Domány G..  (2003)  Indole-2-carboxamides as novel NR2B selective NMDA receptor antagonists.,  13  (21): [PMID:14552795] [10.1016/s0960-894x(03)00708-x]

2. Barta-Szalai G, Borza I, Bozó E, Kiss C, Agai B, Proszenyák A, Keseru GM, Gere A, Kolok S, Galgóczy K, Horváth C, Farkas S, Domány G..  (2004)  Oxamides as novel NR2B selective NMDA receptor antagonists.,  14  (15): [PMID:15225705] [10.1016/j.bmcl.2004.05.053]

3. Borza I, Kolok S, Gere A, Nagy J, Fodor L, Galgóczy K, Fetter J, Bertha F, Agai B, Horváth C, Farkas S, Domány G..  (2006)  Benzimidazole-2-carboxamides as novel NR2B selective NMDA receptor antagonists.,  16  (17): [PMID:16782335] [10.1016/j.bmcl.2006.06.002]

4. Borza I, Bozó E, Barta-Szalai G, Kiss C, Tárkányi G, Demeter A, Gáti T, Háda V, Kolok S, Gere A, Fodor L, Nagy J, Galgóczy K, Magdó I, Agai B, Fetter J, Bertha F, Keserü GM, Horváth C, Farkas S, Greiner I, Domány G..  (2007)  Selective NR1/2B N-methyl-D-aspartate receptor antagonists among indole-2-carboxamides and benzimidazole-2-carboxamides.,  50  (5): [PMID:17290978] [10.1021/jm060420k]

5. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

6. PubChem BioAssay data set, 

7. Lütnant I, Schepmann D, Wünsch B..  (2016)  Benzimidazolone bioisosteres of potent GluN2B selective NMDA receptor antagonists.,  116  [PMID:27061977] [10.1016/j.ejmech.2016.03.065]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names