2-(1H-Indol-3-yl)-N-(4-methoxy-benzyl)-2-oxo-acetamide

ID: ALA306310

Chembl Id: CHEMBL306310

PubChem CID: 1588018

Max Phase: Preclinical

Molecular Formula: C18H16N2O3

Molecular Weight: 308.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CNC(=O)C(=O)c2c[nH]c3ccccc23)cc1

Standard InChI:  InChI=1S/C18H16N2O3/c1-23-13-8-6-12(7-9-13)10-20-18(22)17(21)15-11-19-16-5-3-2-4-14(15)16/h2-9,11,19H,10H2,1H3,(H,20,22)

Standard InChI Key:  STQWWORVIGBLOE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA306310

   2-(1H-indol-3-yl)-N-(4-methoxybenzyl)-2-oxoacetamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 308.34

Molecular Weight (Monoisotopic): 308.1161

AlogP: 2.68

#Rotatable Bonds: 5

Polar Surface Area: 71.19

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.04

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.57

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.56

Np Likeness Score: -0.72

References

1. Primofiore G, Settimo FD, Taliani S, Marini AM, Novellino E, Greco G, Lavecchia A, Besnard F, Trincavelli L, Costa B, Martini C..  (2001)  Novel N-(arylalkyl)indol-3-ylglyoxylylamides targeted as ligands of the benzodiazepine receptor: synthesis, biological evaluation, and molecular modeling analysis of the structure-activity relationships.,  44  (14): [PMID:11428922] [10.1021/jm010827j]

2. Da Settimo A, Primofiore G, Da Settimo F, Marini AM, Novellino E, Greco G, Gesi M, Martini C, Giannaccini G, Lucacchini A..  (1998)  N'-Phenylindol-3-ylglyoxylohydrazide derivatives: synthesis, structure-activity relationships, molecular modeling studies, and pharmacological action on brain benzodiazepine receptors.,  41  (20): [PMID:9748357] [10.1021/jm9800301]

3. Da Settimo A, Primofiore G, Da Settimo F, Marini AM, Novellino E, Greco G, Martini C, Giannaccini G, Lucacchini A..  (1996)  Synthesis, structure-activity relationships, and molecular modeling studies of N-(indol-3-ylglyoxylyl)benzylamine derivatives acting at the benzodiazepine receptor.,  39  (26): [PMID:8978839] [10.1021/jm960240i]

4. Amat L, Carbó-Dorca R, Ponec R..  (1999)  Simple linear QSAR models based on quantum similarity measures.,  42  (25): [PMID:10602702] [10.1021/jm9910728]

5. Taliani S, Cosimelli B, Da Settimo F, Marini AM, La Motta C, Simorini F, Salerno S, Novellino E, Greco G, Cosconati S, Marinelli L, Salvetti F, L'Abbate G, Trasciatti S, Montali M, Costa B, Martini C..  (2009)  Identification of anxiolytic/nonsedative agents among indol-3-ylglyoxylamides acting as functionally selective agonists at the gamma-aminobutyric acid-A (GABAA) alpha2 benzodiazepine receptor.,  52  (12): [PMID:19469479] [10.1021/jm9001154]

6. Thompson MJ, Borsenberger V, Louth JC, Judd KE, Chen B..  (2009)  Design, synthesis, and structure-activity relationship of indole-3-glyoxylamide libraries possessing highly potent activity in a cell line model of prion disease.,  52  (23): [PMID:19842664] [10.1021/jm900920x]

Source

Source(1):

• Scientific Literature