Rac-(2S)-4-benzyl-N-(tert-butyl)-2-isobutyl-7-nitro-3-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine-5-carboxamide

ID: ALA4873014

PubChem CID: 164624782

Max Phase: Preclinical

Molecular Formula: C25H32N4O4

Molecular Weight: 452.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H]1Nc2ccc([N+](=O)[O-])cc2C(C(=O)NC(C)(C)C)N(Cc2ccccc2)C1=O

Standard InChI:  InChI=1S/C25H32N4O4/c1-16(2)13-21-24(31)28(15-17-9-7-6-8-10-17)22(23(30)27-25(3,4)5)19-14-18(29(32)33)11-12-20(19)26-21/h6-12,14,16,21-22,26H,13,15H2,1-5H3,(H,27,30)/t21-,22?/m0/s1

Standard InChI Key:  AGTJLMSHMQGCPS-HMTLIYDFSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.5028  -10.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0942  -11.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9153  -11.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7847  -13.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5232  -13.8071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998  -14.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3561  -15.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784  -15.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8521  -14.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438  -13.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469  -13.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580  -13.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694  -14.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678  -14.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938  -12.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101  -12.2184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865  -12.2026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3884  -10.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4989  -14.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5295  -15.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1703  -13.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9327  -13.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0465  -14.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8080  -14.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4520  -14.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3335  -13.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5719  -13.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0669  -12.8905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2559  -12.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797  -13.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3479  -16.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6949  -16.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151  -15.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 10  4  1  0
  4  5  1  0
  5  6  1  0
  9  7  1  0
  6  8  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  4 15  1  0
 15 16  2  0
 15 17  1  0
 17  2  1  0
  2 18  1  0
  6 19  2  0
  8 20  1  6
  5 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 28 29  1  0
 28 30  2  0
 12 28  1  0
 20 31  1  0
 31 32  1  0
 31 33  1  0
M  CHG  2  28   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4873014

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 452.56

Molecular Weight (Monoisotopic): 452.2424

AlogP: 4.42

#Rotatable Bonds: 6

Polar Surface Area: 104.58

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.86

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.50

Np Likeness Score: -0.68

References

1. Vézina-Dawod S, Perreault M, Guay LD, Gerber N, Gobeil S, Biron E..  (2021)  Synthesis and biological evaluation of novel 1,4-benzodiazepin-3-one derivatives as potential antitumor agents against prostate cancer.,  45  [PMID:34333393] [10.1016/j.bmc.2021.116314]

Source

Source(1):

• Scientific Literature