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

ID: ALA4088629

PubChem CID: 137643689

Max Phase: Preclinical

Molecular Formula: C22H21BrN4O4

Molecular Weight: 485.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C2=NN(CC3CC(Br)=NO3)C(=O)Cc3cc4c(cc32)OCCO4)ccc1N

Standard InChI:  InChI=1S/C22H21BrN4O4/c1-12-6-13(2-3-17(12)24)22-16-10-19-18(29-4-5-30-19)7-14(16)8-21(28)27(25-22)11-15-9-20(23)26-31-15/h2-3,6-7,10,15H,4-5,8-9,11,24H2,1H3

Standard InChI Key:  YYXVQJJRUFHQSF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   23.4985  -20.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4967  -18.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2131  -19.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2120  -19.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8601  -18.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8655  -20.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6697  -18.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6753  -20.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0303  -19.4518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6854  -21.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8989  -21.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7186  -22.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3260  -22.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1165  -22.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2931  -21.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1469  -23.6105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1810  -18.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7854  -19.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7803  -19.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0698  -18.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3596  -19.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3646  -19.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0799  -20.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8566  -19.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2760  -20.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9498  -20.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5682  -21.4552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2786  -21.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0992  -20.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0355  -21.3640    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.7257  -23.1113    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
  9 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 25  1  0
 28 30  1  0
 14 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088629

   ---

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: 485.34

Molecular Weight (Monoisotopic): 484.0746

AlogP: 2.98

#Rotatable Bonds: 3

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: 3.17

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.67

Np Likeness Score: -0.42

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