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

ID: ALA4560186

PubChem CID: 155558213

Max Phase: Preclinical

Molecular Formula: C20H15BrN4OS

Molecular Weight: 439.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(/N=C/c2cccs2)c(C(=O)Nc2ccc(Br)cc2)n2c1CCC2

Standard InChI:  InChI=1S/C20H15BrN4OS/c21-13-5-7-14(8-6-13)24-20(26)19-18(23-12-15-3-2-10-27-15)16(11-22)17-4-1-9-25(17)19/h2-3,5-8,10,12H,1,4,9H2,(H,24,26)/b23-12+

Standard InChI Key:  RBJDLVWWKGFLIS-FSJBWODESA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   23.5025  -14.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0017  -14.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4558  -13.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2478  -13.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2745  -14.6637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0638  -14.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5265  -14.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0206  -13.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2556  -12.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4826  -11.9878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3474  -14.1876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7789  -14.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5998  -14.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1068  -15.4958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.8779  -15.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8471  -14.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0569  -14.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3456  -15.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8148  -16.2924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0925  -17.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5620  -17.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8392  -18.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6485  -18.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1801  -17.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8960  -17.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9274  -19.3761    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   26.1542  -15.8114    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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  2  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
 18 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560186

   ---

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: 439.34

Molecular Weight (Monoisotopic): 438.0150

AlogP: 5.13

#Rotatable Bonds: 4

Polar Surface Area: 70.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.95

CX LogD: 4.95

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -2.10

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