2-Benzylsulfanyl-4-(4-methoxy-phenyl)-6-methyl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester

ID: ALA472767

PubChem CID: 25187073

Max Phase: Preclinical

Molecular Formula: C22H24N2O3S

Molecular Weight: 396.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(SCc2ccccc2)=NC1c1ccc(OC)cc1

Standard InChI:  InChI=1S/C22H24N2O3S/c1-4-27-21(25)19-15(2)23-22(28-14-16-8-6-5-7-9-16)24-20(19)17-10-12-18(26-3)13-11-17/h5-13,20H,4,14H2,1-3H3,(H,23,24)

Standard InChI Key:  PJAYIYLMTNPVCQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.9595  -12.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6716  -12.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3837  -12.0343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3837  -11.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6716  -10.7926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2438  -10.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2456  -12.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5304  -12.0364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2468  -13.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8165  -12.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1014  -12.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0993  -10.7988    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.8127  -11.2134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5285  -10.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6711  -13.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9550  -13.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9546  -14.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6697  -14.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3834  -13.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3862  -14.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6709  -15.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9571  -16.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2385  -11.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9537  -10.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9566   -9.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2382   -9.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5260   -9.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  7  1  0
 14 15  1  0
  1  2  2  0
  2  8  1  0
 16 17  2  0
  1  6  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19 21  1  0
 20 16  1  0
  3 16  1  0
  2  3  1  0
  8 10  2  0
 20 21  2  0
  3  4  1  0
 19 22  1  0
  9 11  1  0
 22 23  1  0
  4  5  2  0
 15 24  2  0
 11 12  1  0
 24 25  1  0
  5  6  1  0
 25 26  2  0
  5 13  1  0
 26 27  1  0
 27 28  2  0
 28 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472767

   Ethyl 2-benzylsulfanyl-4-(4-methoxyphenyl)-6-methyl-1,4-dihydropyrimidine-5-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: 396.51

Molecular Weight (Monoisotopic): 396.1508

AlogP: 4.47

#Rotatable Bonds: 6

Polar Surface Area: 59.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.22

CX LogP: 4.53

CX LogD: 4.53

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -0.87

References

1. Singh BK, Mishra M, Saxena N, Yadav GP, Maulik PR, Sahoo MK, Gaur RL, Murthy PK, Tripathi RP..  (2008)  Synthesis of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines as a new class of antifilarial agents.,  43  (12): [PMID:18339456] [10.1016/j.ejmech.2008.01.038]

Source

Source(1):

• Scientific Literature