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

ID: ALA473084

PubChem CID: 42598034

Max Phase: Preclinical

Molecular Formula: C16H11Cl2N5O2S

Molecular Weight: 408.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(n1)N(c1ccc(Cl)cc1)c1ccc(Cl)cc1S2(=O)=O

Standard InChI:  InChI=1S/C16H11Cl2N5O2S/c17-8-1-4-10(5-2-8)23-11-6-3-9(18)7-12(11)26(24,25)13-14(19)21-16(20)22-15(13)23/h1-7H,(H4,19,20,21,22)

Standard InChI Key:  YJAQUCLZAOJRRL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    6.2170   -5.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2170   -6.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025   -7.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5025   -5.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880   -5.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880   -6.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735   -7.2319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735   -5.5819    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4609   -4.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862   -4.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735   -8.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591   -8.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591   -9.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735   -9.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880   -9.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880   -8.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591   -5.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3591   -6.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446   -7.2319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301   -6.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301   -5.9944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446   -5.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446   -4.7569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157   -7.2319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735  -10.5319    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9314   -5.5819    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
 14 25  1  0
 11 12  2  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA473084

   7-Chloro-10-(4-chlorophenyl)-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: 408.27

Molecular Weight (Monoisotopic): 407.0011

AlogP: 3.56

#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: 3.77

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: -1.21

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