2-Butylsulfanyl-6-methyl-4-naphthalen-1-yl-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester

ID: ALA472825

PubChem CID: 25187362

Max Phase: Preclinical

Molecular Formula: C22H26N2O2S

Molecular Weight: 382.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCSC1=NC(c2cccc3ccccc23)C(C(=O)OCC)=C(C)N1

Standard InChI:  InChI=1S/C22H26N2O2S/c1-4-6-14-27-22-23-15(3)19(21(25)26-5-2)20(24-22)18-13-9-11-16-10-7-8-12-17(16)18/h7-13,20H,4-6,14H2,1-3H3,(H,23,24)

Standard InChI Key:  DCMUJDSCFLKKTB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   12.8500    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8500    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5620   -0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2740    0.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2740    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5620    1.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1343    1.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1361   -0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4211    0.3979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1373   -0.8385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7072   -0.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9921    0.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9897    1.6354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7030    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4187    1.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5616   -0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8455   -1.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8451   -2.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5601   -2.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2738   -1.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2766   -2.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9893   -2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6997   -2.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6929   -1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9797   -0.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1319    1.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8476    1.6270    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  1  0
  3  4  1  0
 21 22  2  0
  9 11  1  0
 22 23  1  0
  4  5  2  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
 25 20  2  0
  5  6  1  0
 15 26  1  0
  5 13  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472825

   Ethyl 2-butylsulfanyl-6-methyl-4-naphthalen-1-yl-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: 382.53

Molecular Weight (Monoisotopic): 382.1715

AlogP: 5.21

#Rotatable Bonds: 6

Polar Surface Area: 50.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.26

CX LogP: 5.28

CX LogD: 5.28

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -0.74

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