4-{3-[4-(4-bromo-benzyl)-piperizin-1-yl]-propoxy}-7-methoxy-3-phenyl-2H-chromen-2-one

ID: ALA2296904

PubChem CID: 76320430

Max Phase: Preclinical

Molecular Formula: C30H31BrN2O4

Molecular Weight: 563.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(OCCCN3CCN(Cc4ccc(Br)cc4)CC3)c(-c3ccccc3)c(=O)oc2c1

Standard InChI:  InChI=1S/C30H31BrN2O4/c1-35-25-12-13-26-27(20-25)37-30(34)28(23-6-3-2-4-7-23)29(26)36-19-5-14-32-15-17-33(18-16-32)21-22-8-10-24(31)11-9-22/h2-4,6-13,20H,5,14-19,21H2,1H3

Standard InChI Key:  UOTAHAZHOMAUIK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   20.6925   -2.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6914   -3.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3994   -3.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3976   -1.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9847   -1.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9845   -0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1062   -2.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1096   -3.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8220   -3.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5356   -3.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5322   -2.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8152   -1.7743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2386   -1.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8242   -4.2418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1176   -4.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4088   -4.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7022   -4.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9934   -4.2495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9898   -3.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2851   -3.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5761   -3.4302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5763   -4.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2856   -4.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2419   -3.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2428   -4.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9508   -4.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6584   -4.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6535   -3.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9450   -3.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8688   -3.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1607   -3.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4543   -3.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7524   -3.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7455   -4.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4575   -4.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1623   -4.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0364   -4.6534    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  7  4  2  0
  4  1  1  0
  1  5  1  0
  5  6  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 10 24  1  0
 21 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
 34 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296904

   4-[3-[4-[(4-Bromophenyl)methyl]piperazin-1-yl]propoxy]-7-methoxy-3-phenylchromen-2-one

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: 563.49

Molecular Weight (Monoisotopic): 562.1467

AlogP: 5.82

#Rotatable Bonds: 9

Polar Surface Area: 55.15

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.97

CX LogP: 5.07

CX LogD: 4.40

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.19

Np Likeness Score: -0.51

References

1. Mandala D, Valeru A, Pochampalli J, Vankadari SR, Tigulla P, Gatla R, Thampu R.  (2013)  Synthesis, antimicrobial activity, and molecular modeling of novel 4-(3-(4-benzylpiperazin-1-yl)propoxy)-7-methoxy-3-substituted phenyl-2H-chromen-2-one,  22  (11): [10.1007/s00044-013-0543-2]

Source

Source(1):

• Scientific Literature