(2-bromophenyl)(2-hydroxy-4,6-dimethoxy-3-((4-methylpiperazin-1-yl)methyl)phenyl)methanone

ID: ALA1093734

PubChem CID: 46884331

Max Phase: Preclinical

Molecular Formula: C21H25BrN2O4

Molecular Weight: 449.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2ccccc2Br)c(O)c1CN1CCN(C)CC1

Standard InChI:  InChI=1S/C21H25BrN2O4/c1-23-8-10-24(11-9-23)13-15-17(27-2)12-18(28-3)19(21(15)26)20(25)14-6-4-5-7-16(14)22/h4-7,12,26H,8-11,13H2,1-3H3

Standard InChI Key:  RVLHOTVUKMRJNN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.9598  -16.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9609  -17.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461  -18.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297  -17.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5325  -16.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2479  -16.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6757  -18.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3899  -17.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2504  -15.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5371  -15.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145  -18.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196  -16.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036  -16.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8227  -15.5978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1038  -17.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3887  -18.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3252  -17.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3195  -16.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3963  -16.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4037  -15.5895    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2463  -18.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9609  -19.3192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6741  -18.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3865  -19.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3910  -20.1423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6768  -20.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9581  -20.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1071  -20.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
  2  7  1  0
 13 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 18  1  0
  6  9  1  0
 18 19  2  0
 19 13  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
  3 21  1  0
  2  3  1  0
 21 22  1  0
 22 23  1  0
  4 11  1  0
  5  6  2  0
  5 12  1  0
  6  1  1  0
 12 13  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1  2  2  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093734

   (2-Bromophenyl)-[2-hydroxy-4,6-dimethoxy-3-[(4-methylpiperazin-1-yl)methyl]phenyl]methanone

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: 449.35

Molecular Weight (Monoisotopic): 448.0998

AlogP: 3.15

#Rotatable Bonds: 6

Polar Surface Area: 62.24

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.09

CX Basic pKa: 7.09

CX LogP: 3.11

CX LogD: 2.92

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -0.29

References

1. Bandgar BP, Patil SA, Totre JV, Korbad BL, Gacche RN, Hote BS, Jalde SS, Chavan HV..  (2010)  Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.,  20  (7): [PMID:20207143] [10.1016/j.bmcl.2010.02.001]

Source

Source(1):

• Scientific Literature