ethyl 2-amino-5-(6,7-dimethoxy-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-ylthio)thiazole-4-carboxylate

ID: ALA2376081

PubChem CID: 72196894

Max Phase: Preclinical

Molecular Formula: C22H20N4O5S2

Molecular Weight: 484.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1nc(N)sc1Sc1nc2cc(OC)c(OC)cc2c(=O)n1-c1ccccc1

Standard InChI:  InChI=1S/C22H20N4O5S2/c1-4-31-19(28)17-20(32-21(23)25-17)33-22-24-14-11-16(30-3)15(29-2)10-13(14)18(27)26(22)12-8-6-5-7-9-12/h5-11H,4H2,1-3H3,(H2,23,25)

Standard InChI Key:  ONXHLHQJGISYDJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.9932  -30.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7080  -30.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7062  -29.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8645  -30.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8611  -29.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1373  -29.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5732  -29.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0020  -29.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9999  -28.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1731  -32.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9981  -32.8291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2508  -32.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6900  -33.5001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0376  -31.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6518  -32.3380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2074  -30.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4820  -33.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0963  -33.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2797  -29.0881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796  -28.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2784  -30.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642  -30.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  2  0
 21 24  1  0
 25 26  1  0
 25 27  2  0
 23 25  1  0
 26 28  1  0
 28 29  1  0
  1 30  1  0
 30 31  1  0
  2 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2376081

   Ethyl 2-amino-5-(6,7-dimethoxy-4-oxo-3-phenylquinazolin-2-yl)sulfanyl-1,3-thiazole-4-carboxylate

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: 484.56

Molecular Weight (Monoisotopic): 484.0875

AlogP: 3.77

#Rotatable Bonds: 7

Polar Surface Area: 118.56

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.37

CX LogP: 4.32

CX LogD: 4.32

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -1.15

References

1. Al-Omary FA, Hassan GS, El-Messery SM, Nagi MN, Habib el-SE, El-Subbagh HI..  (2013)  Nonclassical antifolates, part 3: synthesis, biological evaluation and molecular modeling study of some new 2-heteroarylthio-quinazolin-4-ones.,  63  [PMID:23454532] [10.1016/j.ejmech.2012.12.061]

2. Al-Rashood ST, Hassan GS, El-Messery SM, Nagi MN, Habib el-SE, Al-Omary FA, El-Subbagh HI..  (2014)  Synthesis, biological evaluation and molecular modeling study of 2-(1,3,4-thiadiazolyl-thio and 4-methyl-thiazolyl-thio)-quinazolin-4-ones as a new class of DHFR inhibitors.,  24  (18): [PMID:25139568] [10.1016/j.bmcl.2014.07.070]

Source

Source(1):

• Scientific Literature