4-(6-(3-nitrophenyl)imidazo[2,1-b]thiazol-5-yl)-N-phenylpyrimidin-2-amine

ID: ALA1093235

PubChem CID: 46886312

Max Phase: Preclinical

Molecular Formula: C21H14N6O2S

Molecular Weight: 414.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cccc(-c2nc3sccn3c2-c2ccnc(Nc3ccccc3)n2)c1

Standard InChI:  InChI=1S/C21H14N6O2S/c28-27(29)16-8-4-5-14(13-16)18-19(26-11-12-30-21(26)25-18)17-9-10-22-20(24-17)23-15-6-2-1-3-7-15/h1-13H,(H,22,23,24)

Standard InChI Key:  IWHRJPQDFJDKQC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    4.1389   -3.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378   -4.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8532   -5.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5703   -4.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5675   -3.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8514   -3.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2866   -5.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3738   -5.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0403   -4.6800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5939   -5.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1843   -6.0076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7377   -6.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4894   -6.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4004   -5.4612    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6653   -6.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448   -5.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2354   -6.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6770   -7.0825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -7.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2414   -7.1030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9850   -8.3315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2773   -8.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5598   -8.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8525   -8.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -9.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5939  -10.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2982   -9.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8462   -2.5776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1631   -2.1859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5270   -2.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 15 16  2  0
 16 17  1  0
 17 20  2  0
  8 11  1  0
 19 18  2  0
 18 15  1  0
  8 15  1  0
 19 20  1  0
 10  9  2  0
  9  7  1  0
  4  7  1  0
 10 11  1  0
 19 21  1  0
  4  5  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
  6  1  1  0
 24 25  2  0
  7  8  2  0
 25 26  1  0
 11 12  1  0
 26 27  2  0
 27 22  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  1  2  2  0
 28 29  2  0
 28 30  1  0
  6 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1093235

   4-(6-(3-nitrophenyl)imidazo[2,1-b]thiazol-5-yl)-N-phenylpyrimidin-2-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 414.45

Molecular Weight (Monoisotopic): 414.0899

AlogP: 5.17

#Rotatable Bonds: 5

Polar Surface Area: 98.25

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.20

CX Basic pKa: 2.64

CX LogP: 4.91

CX LogD: 4.91

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: -2.03

References

1. Fidanze SD, Erickson SA, Wang GT, Mantei R, Clark RF, Sorensen BK, Bamaung NY, Kovar P, Johnson EF, Swinger KK, Stewart KD, Zhang Q, Tucker LA, Pappano WN, Wilsbacher JL, Wang J, Sheppard GS, Bell RL, Davidsen SK, Hubbard RD..  (2010)  Imidazo[2,1-b]thiazoles: multitargeted inhibitors of both the insulin-like growth factor receptor and members of the epidermal growth factor family of receptor tyrosine kinases.,  20  (8): [PMID:20346655] [10.1016/j.bmcl.2010.03.015]

Source

Source(1):

• Scientific Literature