2,4-Diamino-7-chloro-10H-(2',5'-dimethylphenyl)-pyrimido-[5,4-b]benzothiazine 5,5-dioxide

ID: ALA475519

PubChem CID: 42598032

Max Phase: Preclinical

Molecular Formula: C18H16ClN5O2S

Molecular Weight: 401.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C)c(N2c3ccc(Cl)cc3S(=O)(=O)c3c(N)nc(N)nc32)c1

Standard InChI:  InChI=1S/C18H16ClN5O2S/c1-9-3-4-10(2)13(7-9)24-12-6-5-11(19)8-14(12)27(25,26)15-16(20)22-18(21)23-17(15)24/h3-8H,1-2H3,(H4,20,21,22,23)

Standard InChI Key:  LBHCREJBLYEXOL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    1.1481   -2.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1481   -3.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336   -3.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336   -2.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809   -2.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809   -3.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -3.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -2.1566    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080   -1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826   -1.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -4.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098   -5.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098   -5.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9953   -6.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809   -5.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809   -5.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098   -2.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098   -3.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243   -3.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1387   -3.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1387   -2.5691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243   -2.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243   -1.3316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8532   -3.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4336   -4.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243   -6.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8626   -2.1566    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  8  1  0
 15 16  2  0
 16 11  1  0
  7 11  1  0
 17 18  2  0
  6  7  1  0
  7 18  1  0
 17  8  1  0
  5  4  2  0
  8  9  2  0
  4  1  1  0
 17 22  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  8 10  2  0
 22 23  1  0
  5  6  1  0
 20 24  1  0
 16 25  1  0
 11 12  2  0
 13 26  1  0
  2  3  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA475519

   7-Chloro-10-(2,5-dimethylphenyl)-5,5-dioxopyrimido[5,4-b][1,4]benzothiazine-2,4-diamine

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: 401.88

Molecular Weight (Monoisotopic): 401.0713

AlogP: 3.53

#Rotatable Bonds: 1

Polar Surface Area: 115.20

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.25

CX LogP: 4.19

CX LogD: 4.19

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: -1.33

References

1. Barazarte A, Lobo G, Gamboa N, Rodrigues JR, Capparelli MV, Alvarez-Larena A, López SE, Charris JE..  (2009)  Synthesis and antimalarial activity of pyrazolo and pyrimido benzothiazine dioxide derivatives.,  44  (3): [PMID:18835067] [10.1016/j.ejmech.2008.08.005]

Source

Source(1):

• Scientific Literature