N-Hydroxy-4-(2-bromoacridin-9-ylamino)benzamide

ID: ALA4796066

PubChem CID: 162673723

Max Phase: Preclinical

Molecular Formula: C20H14BrN3O2

Molecular Weight: 408.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(Nc2c3ccccc3nc3ccc(Br)cc23)cc1

Standard InChI:  InChI=1S/C20H14BrN3O2/c21-13-7-10-18-16(11-13)19(15-3-1-2-4-17(15)23-18)22-14-8-5-12(6-9-14)20(25)24-26/h1-11,26H,(H,22,23)(H,24,25)

Standard InChI Key:  PESSDQDERPAVNH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.4264  -10.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4264  -11.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1317  -11.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1317  -10.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8369  -10.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8380  -11.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5423  -11.6728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5402  -10.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2490  -10.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2539  -11.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9617  -11.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6694  -11.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6645  -10.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9521  -10.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5380   -9.2212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2446   -8.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9545   -9.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6590   -8.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6610   -7.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9524   -7.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2417   -7.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3692   -7.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0765   -7.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3701   -6.7700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0783   -6.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7188  -10.0417    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 19 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4796066

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 408.26

Molecular Weight (Monoisotopic): 407.0269

AlogP: 5.01

#Rotatable Bonds: 3

Polar Surface Area: 74.25

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.25

CX Basic pKa: 7.60

CX LogP: 4.39

CX LogD: 4.15

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.25

Np Likeness Score: -0.91

References

1. Tseng HJ,Lin MH,Shiao YJ,Yang YC,Chu JC,Chen CY,Chen YY,Lin TE,Su CJ,Pan SL,Chen LC,Wang CY,Hsu KC,Huang WJ.  (2020)  Synthesis and biological evaluation of acridine-based histone deacetylase inhibitors as multitarget agents against Alzheimer's disease.,  192  [PMID:32151835] [10.1016/j.ejmech.2020.112193]

2. Hsu KC, Chu JC, Tseng HJ, Liu CI, Wang HC, Lin TE, Lee HS, Hsin LW, Wang AH, Lin CH, Huang WJ..  (2021)  Synthesis and biological evaluation of phenothiazine derivative-containing hydroxamic acids as potent class II histone deacetylase inhibitors.,  219  [PMID:33845233] [10.1016/j.ejmech.2021.113419]

Source

Source(1):

• Scientific Literature