3-methyl-1-(5-phenyl-2-(thiophen-2-yl)thieno[2,3-d]pyrimidin-4-ylamino)-1H-pyrrole-2,5-dione

ID: ALA3290628

PubChem CID: 24898709

Max Phase: Preclinical

Molecular Formula: C21H14N4O2S2

Molecular Weight: 418.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)N(Nc2nc(-c3cccs3)nc3scc(-c4ccccc4)c23)C1=O

Standard InChI:  InChI=1S/C21H14N4O2S2/c1-12-10-16(26)25(21(12)27)24-19-17-14(13-6-3-2-4-7-13)11-29-20(17)23-18(22-19)15-8-5-9-28-15/h2-11H,1H3,(H,22,23,24)

Standard InChI Key:  TUZLYZPPKHVOHU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    2.7815  -21.8687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4911  -21.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4883  -20.6366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797  -20.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734  -21.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747  -20.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941  -20.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8105  -21.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2922  -21.7123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779  -19.4142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4847  -19.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2339  -19.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7794  -18.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3692  -18.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5703  -18.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625  -17.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046  -20.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5923  -18.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005  -21.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904  -22.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916  -22.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5012  -22.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9532  -21.5343    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428  -19.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5910  -19.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403  -18.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5404  -18.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083  -18.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455  -19.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
 15 16  2  0
 12 17  2  0
 13 18  1  0
  2 19  1  0
 22 23  1  0
 20 21  1  0
 19 20  2  0
 21 22  2  0
 23 19  1  0
  7 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3290628

   3-Methyl-1-[(5-phenyl-2-thiophen-2-ylthieno[2,3-d]pyrimidin-4-yl)amino]pyrrole-2,5-dione

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: 418.50

Molecular Weight (Monoisotopic): 418.0558

AlogP: 4.73

#Rotatable Bonds: 4

Polar Surface Area: 75.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.94

CX Basic pKa: 2.24

CX LogP: 5.32

CX LogD: 5.32

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.39

References

1. Park CH, Lee C, Yang JS, Joe BY, Chun K, Kim H, Kim HY, Kang JS, Lee JI, Kim MH, Han G..  (2014)  Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors.,  24  (12): [PMID:24813730] [10.1016/j.bmcl.2014.04.058]

2. Yang JS, Park CH, Lee C, Kim H, Oh C, Choi Y, Kang JS, Yun J, Jeong JH, Kim MH, Han G..  (2014)  Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents.,  85  [PMID:25108079] [10.1016/j.ejmech.2014.08.001]

Source

Source(1):

• Scientific Literature