2-[2-(4-chloroanilino)-3-pyridyl]-10-phenyl-5,10-dihydro-5lambda6-benzo[e][1,2,4]triazolo[1,5-b][1,2,4]thiadiazine-5,5-dione

ID: ALA1927306

PubChem CID: 57395840

Max Phase: Preclinical

Molecular Formula: C25H17ClN6O2S

Molecular Weight: 500.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S1(=O)c2ccccc2N(c2ccccc2)c2nc(-c3cccnc3Nc3ccc(Cl)cc3)nn21

Standard InChI:  InChI=1S/C25H17ClN6O2S/c26-17-12-14-18(15-13-17)28-23-20(9-6-16-27-23)24-29-25-31(19-7-2-1-3-8-19)21-10-4-5-11-22(21)35(33,34)32(25)30-24/h1-16H,(H,27,28)

Standard InChI Key:  JGJGBOHCXWLRJO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 40  0  0  0  0  0  0  0  0999 V2000
    6.1883   -2.3326    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0963   -1.5118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4315   -2.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9972   -4.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9961   -5.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117   -5.9137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4289   -5.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4261   -4.6684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099   -4.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0892   -4.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8766   -4.4207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0801   -3.3478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8628   -3.0844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3494   -3.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1613   -3.6564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0066   -2.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4914   -2.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3048   -2.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6345   -2.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1447   -1.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3330   -1.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1449   -5.9117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461   -6.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4311   -7.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1476   -8.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8645   -7.9693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8600   -7.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6503   -4.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500   -9.2137    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3148   -5.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8029   -5.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6248   -5.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9561   -4.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4658   -4.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 16 17  2  0
  9  4  1  0
 17 18  1  0
  1  3  2  0
 18 19  2  0
  8 10  1  0
 19 20  1  0
 10 11  1  0
 20 21  2  0
 21 16  1  0
  5  6  1  0
  7 22  1  0
 22 23  1  0
 11 14  2  0
 23 24  2  0
 13 12  1  0
 24 25  1  0
 12 10  2  0
 25 26  2  0
 13 14  1  0
 26 27  1  0
  6  7  2  0
 27 28  2  0
 28 23  1  0
  2  1  2  0
 15 29  1  0
  7  8  1  0
 26 30  1  0
 13  1  1  0
 29 31  2  0
 14 15  1  0
 31 32  1  0
 15 17  1  0
 32 33  2  0
 16  1  1  0
 33 34  1  0
  4  5  2  0
 34 35  2  0
 35 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1927306

   N-(4-chlorophenyl)-3-(5,5-dioxo-10-phenyl-[1,2,4]triazolo[1,5-b][1,2,4]benzothiadiazin-2-yl)pyridin-2-amine

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: 500.97

Molecular Weight (Monoisotopic): 500.0822

AlogP: 5.76

#Rotatable Bonds: 4

Polar Surface Area: 93.01

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 4.16

CX LogP: 6.30

CX LogD: 6.30

Aromatic Rings: 5

Heavy Atoms: 35

QED Weighted: 0.33

Np Likeness Score: -1.46

References

1. Kamal A, Srikanth YV, Naseer Ahmed Khan M, Ashraf M, Kashi Reddy M, Sultana F, Kaur T, Chashoo G, Suri N, Sehar I, Wani ZA, Saxena A, Sharma PR, Bhushan S, Mondhe DM, Saxena AK..  (2011)  2-Anilinonicotinyl linked 2-aminobenzothiazoles and [1,2,4]triazolo[1,5-b] [1,2,4]benzothiadiazine conjugates as potential mitochondrial apoptotic inducers.,  19  (23): [PMID:22047801] [10.1016/j.bmc.2011.09.060]

Source

Source(1):

• Scientific Literature