(E)-N-(4-Bromophenyl)-7-cyano-6-((pyridin-3-ylmethylene)amino)-2,3-dihydro-1H-pyrrolizine-5-carboxamide

ID: ALA4531924

PubChem CID: 155546488

Max Phase: Preclinical

Molecular Formula: C21H16BrN5O

Molecular Weight: 434.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(/N=C/c2cccnc2)c(C(=O)Nc2ccc(Br)cc2)n2c1CCC2

Standard InChI:  InChI=1S/C21H16BrN5O/c22-15-5-7-16(8-6-15)26-21(28)20-19(25-13-14-3-1-9-24-12-14)17(11-23)18-4-2-10-27(18)20/h1,3,5-9,12-13H,2,4,10H2,(H,26,28)/b25-13+

Standard InChI Key:  NMTVGDDVOYKQAB-DHRITJCHSA-N

Molfile:  

 
     RDKit          2D

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   32.8355  -14.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3347  -14.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7888  -13.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5808  -13.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6075  -14.5013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3968  -14.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8595  -14.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3536  -13.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5886  -12.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8156  -11.8253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6804  -14.0251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1119  -14.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9328  -14.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3671  -15.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1873  -15.3575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5718  -14.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1302  -13.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3115  -13.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6786  -15.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1478  -16.1300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4255  -16.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8950  -17.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1722  -18.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9815  -18.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5131  -17.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2290  -17.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2604  -19.2136    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   35.4872  -15.6489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  1  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  2  0
  8  9  1  0
  9 10  3  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  6 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 19 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531924

   ---

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: 434.30

Molecular Weight (Monoisotopic): 433.0538

AlogP: 4.47

#Rotatable Bonds: 4

Polar Surface Area: 83.07

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.44

CX LogP: 3.82

CX LogD: 3.82

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -1.76

References

1. Shawky AM, Abourehab MAS, Abdalla AN, Gouda AM..  (2020)  Optimization of pyrrolizine-based Schiff bases with 4-thiazolidinone motif: Design, synthesis and investigation of cytotoxicity and anti-inflammatory potency.,  185  [PMID:31655429] [10.1016/j.ejmech.2019.111780]

Source

Source(1):

• Scientific Literature