N-(2-aminoethyl)-3-(1,3-dimethyl-1H-pyrazolo[4,3-e][1,2,4]triazin-5-yl)-4-ethoxybenzenesulfonamide

ID: ALA3261393

PubChem CID: 90675939

Max Phase: Preclinical

Molecular Formula: C16H21N7O3S

Molecular Weight: 391.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(S(=O)(=O)NCCN)cc1-c1nnc2c(n1)c(C)nn2C

Standard InChI:  InChI=1S/C16H21N7O3S/c1-4-26-13-6-5-11(27(24,25)18-8-7-17)9-12(13)15-19-14-10(2)22-23(3)16(14)21-20-15/h5-6,9,18H,4,7-8,17H2,1-3H3

Standard InChI Key:  JJYNPGHQGVEEBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.8077   -6.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2209   -6.7908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870   -4.0191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -3.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005   -2.7753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4852   -2.3662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7722   -3.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7734   -2.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855   -2.5201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4973   -3.1899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9835   -3.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7274   -4.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7318   -1.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9184   -4.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9148   -4.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6290   -5.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3438   -4.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3398   -4.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6251   -3.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6202   -2.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3322   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3275   -1.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3448   -6.4903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7616   -7.3198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7663   -6.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537   -6.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
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  7  9  1  0
  8  9  2  0
  9 10  1  0
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  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 20 21  1  0
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 22 23  1  0
 17  1  1  0
  1 24  1  0
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 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3261393

   N-(2-aminoethyl)-3-(1,3-dimethylpyrazolo[4,3-e][1,2,4]triazin-5-yl)-4-ethoxybenzenesulfonamide

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: 391.46

Molecular Weight (Monoisotopic): 391.1427

AlogP: 0.37

#Rotatable Bonds: 7

Polar Surface Area: 137.91

Molecular Species: BASE

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.24

CX Basic pKa: 9.10

CX LogP: -0.34

CX LogD: -1.82

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -1.91

References

1. Mojzych M, Bielawska A, Bielawski K, Ceruso M, Supuran CT..  (2014)  Pyrazolo[4,3-e][1,2,4]triazine sulfonamides as carbonic anhydrase inhibitors with antitumor activity.,  22  (9): [PMID:24713308] [10.1016/j.bmc.2014.03.029]

2. Mojzych M, Dolashki A, Voelter W..  (2014)  Synthesis of pyrazolo[4,3-e][1,2,4]triazine sulfonamides, novel Sildenafil analogs with tyrosinase inhibitory activity.,  22  (23): [PMID:25456386] [10.1016/j.bmc.2014.10.009]

3. Mojzych M, Karczmarzyk Z, Wysocki W, Ceruso M, Supuran CT, Kryštof V, Urbańczyk-Lipkowska Z, Kalicki P..  (2015)  New approaches to the synthesis of sildenafil analogues and their enzyme inhibitory activity.,  23  (7): [PMID:25757603] [10.1016/j.bmc.2015.02.026]

4. Alizadeh SR, Ebrahimzadeh MA..  (2021)  Pyrazolotriazines: Biological activities, synthetic strategies and recent developments.,  223  [PMID:34147747] [10.1016/j.ejmech.2021.113537]

Source

Source(1):

• Scientific Literature