ethyl 3-(4-chloro-3-sulfamoylbenzamido)-7-methylpyrazolo[1,5-a]pyrimidine-6-carboxylate

ID: ALA4849958

PubChem CID: 164616133

Max Phase: Preclinical

Molecular Formula: C17H16ClN5O5S

Molecular Weight: 437.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cnc2c(NC(=O)c3ccc(Cl)c(S(N)(=O)=O)c3)cnn2c1C

Standard InChI:  InChI=1S/C17H16ClN5O5S/c1-3-28-17(25)11-7-20-15-13(8-21-23(15)9(11)2)22-16(24)10-4-5-12(18)14(6-10)29(19,26)27/h4-8H,3H2,1-2H3,(H,22,24)(H2,19,26,27)

Standard InChI Key:  XQQVQQFTYJPMFE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    9.2821  -17.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0716  -18.5354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.8632  -18.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7310  -14.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7310  -15.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363  -15.8568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363  -14.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1416  -14.6352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1415  -15.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9197  -15.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4007  -15.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9198  -14.3824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363  -13.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212  -14.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0188  -13.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147  -14.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099  -13.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075  -12.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1722  -16.4835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9715  -16.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2239  -17.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5183  -16.0462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743  -18.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9262  -18.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7263  -18.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2740  -18.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0192  -17.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3291  -19.3135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9798  -19.7591    0.0000 Cl  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
  8  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  7 13  1  0
 14 15  1  0
 14 16  2  0
  4 14  1  0
 15 17  1  0
 17 18  1  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 26  2  1  0
  2 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4849958

   ---

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: 437.87

Molecular Weight (Monoisotopic): 437.0561

AlogP: 1.77

#Rotatable Bonds: 5

Polar Surface Area: 145.75

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.85

CX Basic pKa: 0.60

CX LogP: 1.51

CX LogD: 1.50

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -2.23

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