9-Bromo-5-methyl-12(H)-quino[3,4-b][1,4]benzothiazinium chloride

ID: ALA1278063

PubChem CID: 49845315

Max Phase: Preclinical

Molecular Formula: C16H12BrClN2S

Molecular Weight: 344.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1cc2c(c3ccccc31)Nc1ccc(Br)cc1S2.[Cl-]

Standard InChI:  InChI=1S/C16H11BrN2S.ClH/c1-19-9-15-16(11-4-2-3-5-13(11)19)18-12-7-6-10(17)8-14(12)20-15;/h2-9H,1H3;1H

Standard InChI Key:  FSPJQZAGXIGVPG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   19.4358   -7.4677    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.4503   -6.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4491   -7.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1599   -7.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1581   -6.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8694   -6.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8728   -7.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5879   -7.7334    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.5811   -6.0753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3050   -6.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3060   -7.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0214   -7.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7403   -7.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0193   -6.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7357   -6.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4527   -6.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4544   -5.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7333   -4.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0193   -5.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4516   -7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7346   -7.7368    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
 10 14  1  0
 11 12  1  0
 12 13  2  0
 13 15  1  0
  2  3  2  0
 14 15  2  0
  3  4  1  0
 15 16  1  0
  4  7  2  0
 16 17  2  0
  6  9  1  0
 17 18  1  0
  7  8  1  0
 18 19  2  0
 19 14  1  0
  8 11  1  0
 13 20  1  0
 10  9  1  0
  3 21  1  0
 10 11  2  0
M  CHG  2   1  -1  13   1
M  END

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: 344.26

Molecular Weight (Monoisotopic): 342.9899

AlogP: 4.64

#Rotatable Bonds: ┄

Polar Surface Area: 15.91

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.26

CX LogD: 0.26

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.47

Np Likeness Score: -0.11

References

1. Zięba A, Sochanik A, Szurko A, Rams M, Mrozek A, Cmoch P..  (2010)  Synthesis and in vitro antiproliferative activity of 5-alkyl-12(H)-quino[3,4-b] [1,4]benzothiazinium salts.,  45  (11): [PMID:20813435] [10.1016/j.ejmech.2010.07.035]

2. Pluta K, Jeleń M, Morak-Młodawska B, Zimecki M, Artym J, Kocięba M, Zaczyńska E..  (2017)  Azaphenothiazines - promising phenothiazine derivatives. An insight into nomenclature, synthesis, structure elucidation and biological properties.,  138  [PMID:28734245] [10.1016/j.ejmech.2017.07.009]

Source

Source(1):

• Scientific Literature