1-(5-(tert-butyl)isoxazol-3-yl)-3-(4-(4,5-dihydro-2H-imidazo[2',1':2,3]thiazolo[4,5-e]isoindol-8-yl)phenyl)urea

ID: ALA5183674

PubChem CID: 163322280

Max Phase: Preclinical

Molecular Formula: C25H24N6O2S

Molecular Weight: 472.57

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(NC(=O)Nc2ccc(-c3cn4c5c(sc4n3)CCc3c[nH]cc3-5)cc2)no1

Standard InChI:  InChI=1S/C25H24N6O2S/c1-25(2,3)20-10-21(30-33-20)29-23(32)27-16-7-4-14(5-8-16)18-13-31-22-17-12-26-11-15(17)6-9-19(22)34-24(31)28-18/h4-5,7-8,10-13,26H,6,9H2,1-3H3,(H2,27,29,30,32)

Standard InChI Key:  OAMPOKDQUZAAKE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   -2.3198   -2.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6054   -2.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -2.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -3.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6054   -4.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3198   -3.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065   -4.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -3.4064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064   -2.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -1.7745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9328   -2.4419    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7687   -0.8815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414   -1.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0543    0.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684    0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7676    1.5903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    2.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418    1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    2.8274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6248    2.8274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    4.0645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0893    3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755    4.0595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9818    4.2309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    3.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8423    2.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186    3.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309    4.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186    2.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328    3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  1  6  1  0
  4  7  2  0
  8  7  1  0
  9  8  1  0
  3  9  2  0
  2 10  1  0
 11 10  1  0
 12 11  1  0
  1 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 10 15  1  0
 16 14  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 16 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 27 26  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5183674

   ---

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: 472.57

Molecular Weight (Monoisotopic): 472.1681

AlogP: 6.09

#Rotatable Bonds: 3

Polar Surface Area: 100.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.27

CX Basic pKa: 3.85

CX LogP: 5.74

CX LogD: 5.69

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: -1.69

References

1. Cilibrasi V, Spanò V, Bortolozzi R, Barreca M, Raimondi MV, Rocca R, Maruca A, Montalbano A, Alcaro S, Ronca R, Viola G, Barraja P..  (2022)  Synthesis of 2H-Imidazo[2',1':2,3] [1,3]thiazolo[4,5-e]isoindol-8-yl-phenylureas with promising therapeutic features for the treatment of acute myeloid leukemia (AML) with FLT3/ITD mutations.,  235  [PMID:35339838] [10.1016/j.ejmech.2022.114292]

Source

Source(1):

• Scientific Literature