(E)-1-(2,5-Dimethoxy-phenyl)-3-(4-dimethylamino-phenyl)-2-methyl-propenone

ID: ALA9652

Cas Number: 124711-23-5

PubChem CID: 6439188

Max Phase: Preclinical

Molecular Formula: C20H23NO3

Molecular Weight: 325.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(C(=O)/C(C)=C/c2ccc(N(C)C)cc2)c1

Standard InChI:  InChI=1S/C20H23NO3/c1-14(12-15-6-8-16(9-7-15)21(2)3)20(22)18-13-17(23-4)10-11-19(18)24-5/h6-13H,1-5H3/b14-12+

Standard InChI Key:  AJMWJDGKNKNYEW-WYMLVPIESA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -4.2764   -9.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776  -10.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5628  -10.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8463  -10.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8492   -9.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5646   -9.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363   -9.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203   -9.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394   -8.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4171  -10.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7011  -10.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997  -11.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155  -12.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294  -11.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7236  -10.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079  -10.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -9.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5670   -8.3039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8538   -7.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5630  -11.6069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2775  -12.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460  -11.9961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502  -12.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583  -11.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
  7  8  1  0
  8 17  1  0
  6 18  1  0
  7  9  2  0
 18 19  1  0
  4  5  1  0
  3 20  1  0
  8 10  2  0
 20 21  1  0
  2  3  1  0
 14 22  1  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA9652

   1-(2,5-Dimethoxyphenyl)-3-(4-(dimethylamino)phenyl)-1-methyl-2-propen-1-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: 325.41

Molecular Weight (Monoisotopic): 325.1678

AlogP: 4.06

#Rotatable Bonds: 6

Polar Surface Area: 38.77

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.70

CX LogP: 4.08

CX LogD: 4.08

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: -0.49

References

1. Ducki S, Forrest R, Hadfield JA, Kendall A, Lawrence NJ, McGown AT, Rennison D..  (1998)  Potent antimitotic and cell growth inhibitory properties of substituted chalcones.,  8  (9): [PMID:9871706] [10.1016/s0960-894x(98)00162-0]

2. Edwards ML, Stemerick DM, Sunkara PS..  (1990)  Chalcones: a new class of antimitotic agents.,  33  (7): [PMID:2362275] [10.1021/jm00169a021]

3. Ducki S, Mackenzie G, Lawrence NJ, Snyder JP..  (2005)  Quantitative structure-activity relationship (5D-QSAR) study of combretastatin-like analogues as inhibitors of tubulin assembly.,  48  (2): [PMID:15658859] [10.1021/jm049444m]

4. Ducki S, Rennison D, Woo M, Kendall A, Chabert JF, McGown AT, Lawrence NJ..  (2009)  Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: synthesis and biological evaluation of antivascular activity.,  17  (22): [PMID:19837593] [10.1016/j.bmc.2009.09.039]

5. Mutai P, Breuzard G, Pagano A, Allegro D, Peyrot V, Chibale K..  (2017)  Synthesis and biological evaluation of 4 arylcoumarin analogues as tubulin-targeting antitumor agents.,  25  (5): [PMID:28174064] [10.1016/j.bmc.2017.01.035]

6. Meegan MJ, Nathwani S, Twamley B, Zisterer DM, O'Boyle NM..  (2017)  Piperlongumine (piplartine) and analogues: Antiproliferative microtubule-destabilising agents.,  125  [PMID:27689728] [10.1016/j.ejmech.2016.09.048]

Source

Source(1):

• Scientific Literature