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

ID: ALA485973

PubChem CID: 42598031

Max Phase: Preclinical

Molecular Formula: C17H14ClN5O2S

Molecular Weight: 387.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1N1c2ccc(Cl)cc2S(=O)(=O)c2c(N)nc(N)nc21

Standard InChI:  InChI=1S/C17H14ClN5O2S/c1-9-4-2-3-5-11(9)23-12-7-6-10(18)8-13(12)26(24,25)14-15(19)21-17(20)22-16(14)23/h2-8H,1H3,(H4,19,20,21,22)

Standard InChI Key:  ZSVLEQKGNMDSAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    5.2680    1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2680    0.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5535    0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5535    1.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390    1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390    0.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245    0.1211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245    1.7711    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5119    2.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7372    2.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245   -0.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101   -1.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101   -1.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245   -2.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390   -1.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390   -1.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101    1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4101    0.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    0.1211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9811    0.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9811    1.3586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    1.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6956    2.5961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667    0.1211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5535   -0.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    1.7711    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  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
 16 25  1  0
 11 12  2  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA485973

   7-Chloro-10-(2-methylphenyl)-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: 387.85

Molecular Weight (Monoisotopic): 387.0557

AlogP: 3.22

#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: 3.68

CX LogD: 3.68

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.25

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