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

ID: ALA4557315

PubChem CID: 155554424

Max Phase: Preclinical

Molecular Formula: C22H17BrN4O2

Molecular Weight: 449.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(/N=C/c2ccc(O)cc2)c(C(=O)Nc2ccc(Br)cc2)n2c1CCC2

Standard InChI:  InChI=1S/C22H17BrN4O2/c23-15-5-7-16(8-6-15)26-22(29)21-20(18(12-24)19-2-1-11-27(19)21)25-13-14-3-9-17(28)10-4-14/h3-10,13,28H,1-2,11H2,(H,26,29)/b25-13+

Standard InChI Key:  RUYOIFKVHOOUJH-DHRITJCHSA-N

Molfile:  

 
     RDKit          2D

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   30.0552   -4.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5544   -3.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0085   -2.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8005   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8272   -4.0377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6165   -4.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0792   -3.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5733   -2.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8083   -2.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0353   -1.3617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9001   -3.5615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3316   -4.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1525   -4.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8983   -5.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3675   -5.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7069   -5.1853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6452   -6.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1147   -7.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3919   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2012   -7.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7328   -7.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4487   -6.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4801   -8.7500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   34.5868   -4.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4070   -4.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7915   -4.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3499   -3.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5312   -3.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6081   -4.1353    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
  9 10  3  0
  8  9  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 20 23  1  0
 13 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 13  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557315

   ---

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: 449.31

Molecular Weight (Monoisotopic): 448.0535

AlogP: 4.78

#Rotatable Bonds: 4

Polar Surface Area: 90.41

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.12

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.66

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: -1.30

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