2,4-Diamino-7-chloro-10H-phenyl-pyrimido-[5,4-b]benzothiazine 5,5-dioxide

ID: ALA454562

PubChem CID: 42598030

Max Phase: Preclinical

Molecular Formula: C16H12ClN5O2S

Molecular Weight: 373.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(n1)N(c1ccccc1)c1ccc(Cl)cc1S2(=O)=O

Standard InChI:  InChI=1S/C16H12ClN5O2S/c17-9-6-7-11-12(8-9)25(23,24)13-14(18)20-16(19)21-15(13)22(11)10-4-2-1-3-5-10/h1-8H,(H4,18,19,20,21)

Standard InChI Key:  XZABUPQKIKWNNU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    1.1016    1.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871    0.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871    1.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    1.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418    0.1472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418    1.7972    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6545    2.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291    2.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418   -0.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -1.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -1.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418   -2.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    1.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707    0.1472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1852    0.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1852    1.3847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707    1.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707    2.6222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8997    0.1472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161    1.7972    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  2  3  1  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
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA454562

   7-Chloro-5,5-dioxo-10-phenylpyrimido[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: 373.83

Molecular Weight (Monoisotopic): 373.0400

AlogP: 2.91

#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: 3.17

CX LogD: 3.17

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -1.26

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