6-(4-Amino-3-methyl-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: ALA4082987

PubChem CID: 137646724

Max Phase: Preclinical

Molecular Formula: C21H19BrN4O4

Molecular Weight: 471.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C2=NN(C3CC(Br)=NO3)C(=O)Cc3cc4c(cc32)OCCO4)ccc1N

Standard InChI:  InChI=1S/C21H19BrN4O4/c1-11-6-12(2-3-15(11)23)21-14-9-17-16(28-4-5-29-17)7-13(14)8-19(27)26(24-21)20-10-18(22)25-30-20/h2-3,6-7,9,20H,4-5,8,10,23H2,1H3

Standard InChI Key:  ZFLZKUXNIGTYRS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   23.1742  -13.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1724  -11.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8888  -12.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8877  -12.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5359  -11.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5412  -13.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3455  -11.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3511  -13.2874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7060  -12.5359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3611  -14.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5746  -14.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3942  -15.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0017  -15.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7923  -15.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9689  -14.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8226  -16.6946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8567  -11.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4611  -12.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4560  -12.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7454  -11.7357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0351  -12.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0402  -12.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7554  -13.3802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5323  -12.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0201  -13.1932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8036  -12.9348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8001  -12.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0144  -11.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4654  -11.6219    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.4013  -16.1954    0.0000 C   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
 14 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4082987

   ---

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: 471.31

Molecular Weight (Monoisotopic): 470.0590

AlogP: 2.94

#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: 3.15

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.68

Np Likeness Score: -0.36

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