(2Z,4Z)-N-(4-Chlorophenyl)-8-methoxy-[1,3,4]thiadiazepino[7,6-b]quinolin-2-amine

ID: ALA2298571

PubChem CID: 136240249

Max Phase: Preclinical

Molecular Formula: C18H13ClN4OS

Molecular Weight: 368.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2nc3c(cc2c1)C=NN=C(Nc1ccc(Cl)cc1)S3

Standard InChI:  InChI=1S/C18H13ClN4OS/c1-24-15-6-7-16-11(9-15)8-12-10-20-23-18(25-17(12)22-16)21-14-4-2-13(19)3-5-14/h2-10H,1H3,(H,21,23)

Standard InChI Key:  AAXFPXMORXYEPO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   16.9367   -9.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9356  -10.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6436  -11.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6418   -9.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3505   -9.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3512  -10.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0598  -11.0452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0542   -9.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7734  -10.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7633   -9.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4009   -9.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4266  -11.1380    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.2065   -9.4547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2284  -10.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5726  -10.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8740  -11.4413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8723  -12.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2289   -9.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1593  -12.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1528  -13.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8579  -13.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5710  -13.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5741  -12.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8528  -14.7056    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.5213   -9.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  2  0
 10  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 11 13  2  0
 12 14  1  0
 13 15  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  1 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 21 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2298571

   ---

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: 368.85

Molecular Weight (Monoisotopic): 368.0499

AlogP: 4.80

#Rotatable Bonds: 2

Polar Surface Area: 58.87

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.32

CX LogP: 4.94

CX LogD: 4.94

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -0.98

References

1. Raza HM, Rizvi N, Siddiqui HL, Javaid A, Iqbal M.  (2013)  Synthesis and biological evaluation of new [1,3,4]thiadiazepino[7,6-b]quinolin-2-amines as potent anti-microbial agents,  22  (8): [10.1007/s00044-012-0389-z]

Source

Source(1):

• Scientific Literature