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

ID: ALA5173972

PubChem CID: 168277660

Max Phase: Preclinical

Molecular Formula: C33H40N8O2S

Molecular Weight: 612.80

Names and Identifiers

Canonical SMILES:  CN1CCN(CCCn2cc3c(c2)-c2c(sc4nc(-c5ccc(NC(=O)Nc6cc(C(C)(C)C)on6)cc5)cn24)CC3)CC1

Standard InChI:  InChI=1S/C33H40N8O2S/c1-33(2,3)28-18-29(37-43-28)36-31(42)34-24-9-6-22(7-10-24)26-21-41-30-25-20-40(13-5-12-39-16-14-38(4)15-17-39)19-23(25)8-11-27(30)44-32(41)35-26/h6-7,9-10,18-21H,5,8,11-17H2,1-4H3,(H2,34,36,37,42)

Standard InChI Key:  GKEDSPHGEOCZKN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 44 50  0  0  0  0  0  0  0  0999 V2000
   -2.8984   -2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840   -2.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695   -2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4695   -3.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1840   -4.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8984   -3.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -4.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1999   -3.4068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6848   -2.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -3.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0372   -2.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619   -2.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -1.9782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619   -1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -0.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0991   -0.5497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116   -1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0991   -1.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5116    0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3555   -1.7747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759   -1.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5116   -2.4422    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3473   -0.8816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6328   -0.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0199   -1.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6328    0.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471    0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463    1.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318    2.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203    1.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155    0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318    2.8278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    3.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2033    2.8278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9175    4.0649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4890    3.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    4.0600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035    4.2314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157    3.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    2.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    3.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0528    4.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    2.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548    3.1051    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
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 13 18  1  0
 16 19  1  0
  2 20  1  0
 21 20  1  0
 22 21  1  0
  1 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 20 25  1  0
 26 24  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 30 29  1  0
 31 30  2  0
 26 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 34 36  1  0
 37 36  2  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 36  1  0
 39 41  1  0
 41 42  1  0
 41 43  1  0
 41 44  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5173972

   ---

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: 612.80

Molecular Weight (Monoisotopic): 612.2995

AlogP: 6.20

#Rotatable Bonds: 7

Polar Surface Area: 95.87

Molecular Species: BASE

HBA: 9

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.12

CX Basic pKa: 8.80

CX LogP: 5.00

CX LogD: 4.59

Aromatic Rings: 5

Heavy Atoms: 44

QED Weighted: 0.23

Np Likeness Score: -1.68

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