5-nitro-N-(4-(7-(1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)phenyl)furan-2-carboxamide

ID: ALA5284687

Max Phase: Preclinical

Molecular Formula: C23H19N5O4

Molecular Weight: 429.44

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(-c2cnc3cc(C4=CCNCC4)ccn23)cc1)c1ccc([N+](=O)[O-])o1

Standard InChI:  InChI=1S/C23H19N5O4/c29-23(20-5-6-22(32-20)28(30)31)26-18-3-1-16(2-4-18)19-14-25-21-13-17(9-12-27(19)21)15-7-10-24-11-8-15/h1-7,9,12-14,24H,8,10-11H2,(H,26,29)

Standard InChI Key:  CMVDOFFRPTYZID-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -0.3190    0.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3190   -0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014   -0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3925    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8127   -0.8214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240   -0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351   -0.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850   -0.4876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5344   -1.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1239   -1.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210   -1.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3557   -1.0977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -0.3865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7663   -1.8090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240    0.4103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0307    0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1166    1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200    1.8090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3307    1.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    0.4871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346   -0.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8382   -0.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3865    0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1375    0.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -0.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7605    0.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5538    0.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7663   -0.4939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857   -1.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3923   -0.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  2  0
 14 11  1  0
 14 15  2  0
 14 16  1  0
  8 17  2  0
 18  1  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 18 22  1  0
 22 21  1  0
 22 23  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 21 26  1  0
 27 25  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 27 32  1  0
M  CHG  2  14   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5284687

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 429.44

Molecular Weight (Monoisotopic): 429.1437

AlogP: 4.13

#Rotatable Bonds: 5

Polar Surface Area: 114.71

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.62

CX Basic pKa: 9.51

CX LogP: 2.50

CX LogD: 0.41

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: -1.29

References

1. Li H, Ouyang S, Zhang Y, Peng K, Fang W, Liu Z, Wang CY, Zhang X, Wang Y..  (2022)  Structural optimization of Imidazo[1, 2-a]pyridine derivatives for the treatment of gastric cancer via STAT3 signaling pathway.,  244  [PMID:36283181] [10.1016/j.ejmech.2022.114858]

Source

Source(1):

• Scientific Literature