N-(3,4-Dimethoxy-benzyl)-2-(5-nitro-1H-indol-3-yl)-2-oxo-acetamide

ID: ALA308760

Chembl Id: CHEMBL308760

PubChem CID: 10643674

Max Phase: Preclinical

Molecular Formula: C19H17N3O6

Molecular Weight: 383.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CNC(=O)C(=O)c2c[nH]c3ccc([N+](=O)[O-])cc23)cc1OC

Standard InChI:  InChI=1S/C19H17N3O6/c1-27-16-6-3-11(7-17(16)28-2)9-21-19(24)18(23)14-10-20-15-5-4-12(22(25)26)8-13(14)15/h3-8,10,20H,9H2,1-2H3,(H,21,24)

Standard InChI Key:  HFPZDEHIDKJZSN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA308760

   N-[(3,4-dimethoxyphenyl)methyl]-2-(5-nitro-1H-indol-3-yl)-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: 383.36

Molecular Weight (Monoisotopic): 383.1117

AlogP: 2.59

#Rotatable Bonds: 7

Polar Surface Area: 123.56

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.18

CX Basic pKa: ┄

CX LogP: 2.36

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: -0.95

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]

Source

Source(1):

• Scientific Literature