N-(4-Chloro-benzyl)-2-(1H-indol-3-yl)-2-oxo-acetamide

ID: ALA73288

Chembl Id: CHEMBL73288

Cas Number: 61-38-1

PubChem CID: 5304328

Max Phase: Preclinical

Molecular Formula: C17H13ClN2O2

Molecular Weight: 312.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(Cl)cc1)C(=O)c1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C17H13ClN2O2/c18-12-7-5-11(6-8-12)9-20-17(22)16(21)14-10-19-15-4-2-1-3-13(14)15/h1-8,10,19H,9H2,(H,20,22)

Standard InChI Key:  WCYJVRQPVHPWLQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA73288

   N-(4-chlorobenzyl)-2-(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: 312.76

Molecular Weight (Monoisotopic): 312.0666

AlogP: 3.32

#Rotatable Bonds: 4

Polar Surface Area: 61.96

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.91

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -0.99

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. PubChem BioAssay data set, 

6. Schmidt S, Preu L, Lemcke T, Totzke F, Schächtele C, Kubbutat MH, Kunick C..  (2011)  Dual IGF-1R/SRC inhibitors based on a N'-aroyl-2-(1H-indol-3-yl)-2-oxoacetohydrazide structure.,  46  (7): [PMID:21524503] [10.1016/j.ejmech.2011.03.065]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays