N-(2-aminophenyl)-4-(1-(2-(thiophen-3-yl)ethyl)-1H-1,2,3-triazol-4-yl)benzamide

ID: ALA3622374

Cas Number: 1451042-18-4

PubChem CID: 71721946

Product Number: N159027, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H19N5OS

Molecular Weight: 389.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)c1ccc(-c2cn(CCc3ccsc3)nn2)cc1

Standard InChI:  InChI=1S/C21H19N5OS/c22-18-3-1-2-4-19(18)23-21(27)17-7-5-16(6-8-17)20-13-26(25-24-20)11-9-15-10-12-28-14-15/h1-8,10,12-14H,9,11,22H2,(H,23,27)

Standard InChI Key:  LBLSLSOENGWIHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1924   -6.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4914   -5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -3.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8541   -5.8570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511    0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9530    1.9978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010    3.2957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342    2.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4436    1.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3221    3.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8153    2.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7954    4.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1667    3.4228    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0124    1.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5457    1.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 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
 11 16  1  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 17  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3622374

   HDAC3-IN-T247

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: 389.48

Molecular Weight (Monoisotopic): 389.1310

AlogP: 4.08

#Rotatable Bonds: 6

Polar Surface Area: 85.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.27

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -2.18

References

1. Zhan P, Itoh Y, Suzuki T, Liu X..  (2015)  Strategies for the Discovery of Target-Specific or Isoform-Selective Modulators.,  58  (19): [PMID:26086931] [10.1021/acs.jmedchem.5b00229]

2. Reddy DN, Ballante F, Chuang T, Pirolli A, Marrocco B, Marshall GR..  (2016)  Design and Synthesis of Simplified Largazole Analogues as Isoform-Selective Human Lysine Deacetylase Inhibitors.,  59  (4): [PMID:26681404] [10.1021/acs.jmedchem.5b01632]

3. Reddy DR, Ballante F, Zhou NJ, Marshall GR..  (2017)  Design and synthesis of benzodiazepine analogs as isoform-selective human lysine deacetylase inhibitors.,  127  [PMID:28109947] [10.1016/j.ejmech.2016.12.032]

4. Ballante F, Reddy DR, Zhou NJ, Marshall GR..  (2017)  Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy.,  25  (7): [PMID:28259528] [10.1016/j.bmc.2017.02.020]

5. Huang L, Lai WH, Zhu L, Li W, Wei L, Lee KH, Xie L, Chen CH..  (2018)  Elimination of HIV-1 Latently Infected Cells by Gnidimacrin and a Selective HDAC Inhibitor.,  9  (3): [PMID:29541372] [10.1021/acsmedchemlett.8b00012]

6. Wu G, Zhao T, Kang D, Zhang J, Song Y, Namasivayam V, Kongsted J, Pannecouque C, De Clercq E, Poongavanam V, Liu X, Zhan P..  (2019)  Overview of Recent Strategic Advances in Medicinal Chemistry.,  62  (21): [PMID:31050421] [10.1021/acs.jmedchem.9b00359]

7. Amin SA, Adhikari N, Kotagiri S, Jha T, Ghosh B..  (2019)  Histone deacetylase 3 inhibitors in learning and memory processes with special emphasis on benzamides.,  166  [PMID:30735902] [10.1016/j.ejmech.2019.01.077]

8. Sarkar R, Banerjee S, Amin SA, Adhikari N, Jha T..  (2020)  Histone deacetylase 3 (HDAC3) inhibitors as anticancer agents: A review.,  192  [PMID:32163814] [10.1016/j.ejmech.2020.112171]

Source

Source(1):

• Scientific Literature