6-(4-Amino-phenyl)-8-(3-bromo-4,5-dihydro-isoxazol-5-yl)-2,3,8,10-tetrahydro-1,4-dioxa-7,8-diaza-cyclohepta[b]naphthalen-9-one

ID: ALA4097333

PubChem CID: 137660839

Max Phase: Preclinical

Molecular Formula: C20H17BrN4O4

Molecular Weight: 457.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(C2=NN(C3CC(Br)=NO3)C(=O)Cc3cc4c(cc32)OCCO4)cc1

Standard InChI:  InChI=1S/C20H17BrN4O4/c21-17-10-19(29-24-17)25-18(26)8-12-7-15-16(28-6-5-27-15)9-14(12)20(23-25)11-1-3-13(22)4-2-11/h1-4,7,9,19H,5-6,8,10,22H2

Standard InChI Key:  WXZDBSUEQSNNNB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   14.4702  -13.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4684  -11.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1849  -13.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1838  -12.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8319  -11.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8373  -13.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6416  -11.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6471  -13.4541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0022  -12.7025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6572  -14.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8706  -14.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6903  -15.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2978  -16.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0883  -15.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2649  -15.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1187  -16.8613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1528  -11.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7571  -13.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7521  -12.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0415  -11.9024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3312  -12.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3363  -13.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0516  -13.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8284  -12.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3163  -13.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0998  -13.1014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0961  -12.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3104  -12.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7614  -11.7886    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  0
  1  3  2  0
  4  2  2  0
  2 19  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  5  7  1  0
  6  8  2  0
  7  9  1  0
  8  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
  7 17  2  0
 18 19  2  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
  9 24  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097333

   ---

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: 457.28

Molecular Weight (Monoisotopic): 456.0433

AlogP: 2.63

#Rotatable Bonds: 2

Polar Surface Area: 98.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.30

CX LogP: 2.56

CX LogD: 2.56

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -0.23

References

1. Espahbodinia M, Ettari R, Wen W, Wu A, Shen YC, Niu L, Grasso S, Zappalà M..  (2017)  Development of novel N-3-bromoisoxazolin-5-yl substituted 2,3-benzodiazepines as noncompetitive AMPAR antagonists.,  25  (14): [PMID:28571973] [10.1016/j.bmc.2017.05.036]

Source

Source(1):

• Scientific Literature