(E)-3-(3,4-dimethoxybenzylidene)-6-((3-(dimethylamino)propyl)amino)-7-fluoro-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one

ID: ALA4066570

PubChem CID: 137633202

Max Phase: Preclinical

Molecular Formula: C25H29FN4O3

Molecular Weight: 452.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\CCn3c2nc2cc(NCCCN(C)C)c(F)cc2c3=O)cc1OC

Standard InChI:  InChI=1S/C25H29FN4O3/c1-29(2)10-5-9-27-21-15-20-18(14-19(21)26)25(31)30-11-8-17(24(30)28-20)12-16-6-7-22(32-3)23(13-16)33-4/h6-7,12-15,27H,5,8-11H2,1-4H3/b17-12+

Standard InChI Key:  BATNSXHOXMHTAJ-SFQUDFHCSA-N

Molfile:  

     RDKit          2D

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   10.5753   -6.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8266   -7.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6228   -7.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8748   -7.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6743   -8.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9703   -6.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1743   -6.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9695   -5.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9683   -5.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6805   -6.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6787   -4.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3832   -5.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3862   -6.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0882   -6.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0906   -4.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0906   -3.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562   -6.4155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5405   -6.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8366   -6.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7994   -5.1827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8020   -6.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0558   -5.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5778   -4.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2544   -4.7736    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264   -6.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -6.4271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110   -6.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262   -7.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0189   -7.7244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9243   -8.9325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3755   -9.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2686   -8.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  8  3  1  0
  9 10  2  0
 10 11  1  0
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 13 12  2  0
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 10 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  1  0
 22  1  1  0
  1 23  1  0
 23 24  1  0
 24 21  1  0
  9 25  1  0
 20 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
  5 31  1  0
 31 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4066570

   ---

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: 452.53

Molecular Weight (Monoisotopic): 452.2224

AlogP: 3.86

#Rotatable Bonds: 8

Polar Surface Area: 68.62

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.40

CX LogP: 2.66

CX LogD: 0.67

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: -0.88

References

1. Wang YQ, Huang ZL, Chen SB, Wang CX, Shan C, Yin QK, Ou TM, Li D, Gu LQ, Tan JH, Huang ZS..  (2017)  Design, Synthesis, and Evaluation of New Selective NM23-H2 Binders as c-MYC Transcription Inhibitors via Disruption of the NM23-H2/G-Quadruplex Interaction.,  60  (16): [PMID:28714689] [10.1021/acs.jmedchem.7b00421]

Source

Source(1):

• Scientific Literature