N-Benzyl-2-(5-nitro-1H-indol-3-yl)-2-oxo-acetamide

ID: ALA75307

Chembl Id: CHEMBL75307

PubChem CID: 10426330

Max Phase: Preclinical

Molecular Formula: C17H13N3O4

Molecular Weight: 323.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccccc1)C(=O)c1c[nH]c2ccc([N+](=O)[O-])cc12

Standard InChI:  InChI=1S/C17H13N3O4/c21-16(17(22)19-9-11-4-2-1-3-5-11)14-10-18-15-7-6-12(20(23)24)8-13(14)15/h1-8,10,18H,9H2,(H,19,22)

Standard InChI Key:  JYXHNHBKWZQGLB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA75307

   N-benzyl-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: 323.31

Molecular Weight (Monoisotopic): 323.0906

AlogP: 2.58

#Rotatable Bonds: 5

Polar Surface Area: 105.10

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.23

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.33

Np Likeness Score: -1.19

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. Primofiore G, Taliani S, Da Settimo F, Marini AM, La Motta C, Simorini F, Patrizi MP, Sergianni V, Novellino E, Greco G, Cosimelli B, Calderone V, Montali M, Besnard F, Martini C..  (2007)  Novel N-substituted indol-3-ylglyoxylamides probing the LDi and L1/L2 lipophilic regions of the benzodiazepine receptor site in search for subtype-selective ligands.,  50  (7): [PMID:17335185] [10.1021/jm0607707]

6. 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]

7. Robello M, Barresi E, Baglini E, Salerno S, Taliani S, Settimo FD..  (2021)  The Alpha Keto Amide Moiety as a Privileged Motif in Medicinal Chemistry: Current Insights and Emerging Opportunities.,  64  (7.0): [PMID:33764065] [10.1021/acs.jmedchem.0c01808]

Source

Source(1):

• Scientific Literature