N-(2-aminophenyl)-5-(1-(3-nitrophenethyl)-1H-1,2,3-triazol-4-yl)thiophene-2-carboxamide

ID: ALA3622375

Cas Number: 1451042-19-5

PubChem CID: 71721558

Max Phase: Preclinical

Molecular Formula: C21H18N6O3S

Molecular Weight: 434.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccccc1NC(=O)c1ccc(-c2cn(CCc3cccc([N+](=O)[O-])c3)nn2)s1

Standard InChI:  InChI=1S/C21H18N6O3S/c22-16-6-1-2-7-17(16)23-21(28)20-9-8-19(31-20)18-13-26(25-24-18)11-10-14-4-3-5-15(12-14)27(29)30/h1-9,12-13H,10-11,22H2,(H,23,28)

Standard InChI Key:  AXAUXMXVFLCQQK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    6.1088   -6.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2447   -3.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    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
   -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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.7031    0.0000 O   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
    5.4538   -8.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5416   -9.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8600   -8.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5870   -7.0931    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2135   -9.2105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4493   -8.3590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3095  -10.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8051   -9.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9226  -10.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2764  -11.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5127  -10.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3953   -8.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0416   -8.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9477   -6.9570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  2  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 15 16  2  0
 15 17  1  0
 13 15  1  0
  1 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21  1  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 30 31  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3622375

   2-Thiophenecarboxamide, N-(2-aminophenyl)-5-[1-[2-(3-nitrophenyl)ethyl]-1H-1,2,3-triazol-4-yl]-

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: 434.48

Molecular Weight (Monoisotopic): 434.1161

AlogP: 3.99

#Rotatable Bonds: 7

Polar Surface Area: 128.97

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.11

CX LogP: 4.18

CX LogD: 4.18

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.26

Np Likeness Score: -1.89

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. Bourguet E, Ozdarska K, Moroy G, Jeanblanc J, Naassila M..  (2018)  Class I HDAC Inhibitors: Potential New Epigenetic Therapeutics for Alcohol Use Disorder (AUD).,  61  (5): [PMID:28771357] [10.1021/acs.jmedchem.7b00115]

3. 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]

4. 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]

5. 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