ethyl 7-methyl-3-(3-(4-sulfamoylphenethyl)ureido)pyrazolo[1,5-a]pyrimidine-6-carboxylate

ID: ALA4867657

PubChem CID: 164618855

Max Phase: Preclinical

Molecular Formula: C19H22N6O5S

Molecular Weight: 446.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc2c(NC(=O)NCCc3ccc(S(N)(=O)=O)cc3)cnn2c1C

Standard InChI:  InChI=1S/C19H22N6O5S/c1-3-30-18(26)15-10-22-17-16(11-23-25(17)12(15)2)24-19(27)21-9-8-13-4-6-14(7-5-13)31(20,28)29/h4-7,10-11H,3,8-9H2,1-2H3,(H2,20,28,29)(H2,21,24,27)

Standard InChI Key:  MMZBHZUVIYNBBK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.5347   -8.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9474   -8.7910    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.3558   -8.0786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6517   -9.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6517  -10.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3569  -10.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3569   -9.2698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0622   -9.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0667  -10.4961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8419  -10.7434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3166  -10.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8347   -9.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3574  -11.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9437  -10.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2354  -10.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9449  -11.7279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5283  -10.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8200  -10.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0829   -8.6483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8813   -8.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1296   -7.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4315   -9.0783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2298   -8.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7800   -9.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5723   -9.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1196   -9.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9112   -9.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1529   -8.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5969   -8.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8073   -8.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5052   -9.3918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  7  2  0
  5  6  2  0
  6  9  1  0
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  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
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  6 13  1  0
 14 15  1  0
 14 16  2  0
  5 14  1  0
 15 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 25 24  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
 28  2  1  0
  2 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4867657

   ---

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: 446.49

Molecular Weight (Monoisotopic): 446.1372

AlogP: 1.23

#Rotatable Bonds: 7

Polar Surface Area: 157.78

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.16

CX Basic pKa: 0.59

CX LogP: 0.96

CX LogD: 0.96

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -1.91

References

1. Gumus A, Bozdag M, Angeli A, Peat TS, Carta F, Supuran CT, Selleri S..  (2021)  Privileged scaffolds in medicinal chemistry: Studies on pyrazolo[1,5-a]pyrimidines on sulfonamide containing Carbonic Anhydrase inhibitors.,  49  [PMID:34371130] [10.1016/j.bmcl.2021.128309]

Source

Source(1):

• Scientific Literature