ID: ALA41910

Max Phase: Preclinical

Molecular Formula: C19H24ClN5S

Molecular Weight: 389.96

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCCNc1nc(SCC)nc2c1cnn2CC(Cl)c1ccccc1

Standard InChI:  InChI=1S/C19H24ClN5S/c1-3-5-11-21-17-15-12-22-25(18(15)24-19(23-17)26-4-2)13-16(20)14-9-7-6-8-10-14/h6-10,12,16H,3-5,11,13H2,1-2H3,(H,21,23,24)

Standard InChI Key:  RIIKNMAPWOLEED-UHFFFAOYSA-N

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

Properties

Molecular Weight: 389.96

Molecular Weight (Monoisotopic): 389.1441

AlogP: 5.13

#Rotatable Bonds: 9

Polar Surface Area: 55.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 3.88

CX LogP: 5.26

CX LogD: 5.26

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.24

Np Likeness Score: -1.95

References

1. Carraro F, Pucci A, Naldini A, Schenone S, Bruno O, Ranise A, Bondavalli F, Brullo C, Fossa P, Menozzi G, Mosti L, Manetti F, Botta M..  (2004)  Pyrazolo[3,4-d]pyrimidines endowed with antiproliferative activity on ductal infiltrating carcinoma cells.,  47  (7): [PMID:15027847] [10.1021/jm034257u]

2. Schenone S, Bruno O, Ranise A, Bondavalli F, Brullo C, Fossa P, Mosti L, Menozzi G, Carraro F, Naldini A, Bernini C, Manetti F, Botta M..  (2004)  New pyrazolo[3,4-d]pyrimidines endowed with A431 antiproliferative activity and inhibitory properties of Src phosphorylation.,  14  (10): [PMID:15109642] [10.1016/j.bmcl.2004.03.013]

3. Carraro F, Naldini A, Pucci A, Locatelli GA, Maga G, Schenone S, Bruno O, Ranise A, Bondavalli F, Brullo C, Fossa P, Menozzi G, Mosti L, Modugno M, Tintori C, Manetti F, Botta M..  (2006)  Pyrazolo[3,4-d]pyrimidines as potent antiproliferative and proapoptotic agents toward A431 and 8701-BC cells in culture via inhibition of c-Src phosphorylation.,  49  (5): [PMID:16509573] [10.1021/jm050603r]

4. Tintori C, Magnani M, Schenone S, Botta M..  (2009)  Docking, 3D-QSAR studies and in silico ADME prediction on c-Src tyrosine kinase inhibitors.,  44  (3): [PMID:18722033] [10.1016/j.ejmech.2008.07.002]

5. Vignaroli G, Zamperini C, Dreassi E, Radi M, Angelucci A, Sanità P, Crespan E, Kissova M, Maga G, Schenone S, Musumeci F, Botta M..  (2013)  Pyrazolo[3,4-d]pyrimidine Prodrugs: Strategic Optimization of the Aqueous Solubility of Dual Src/Abl Inhibitors.,  4  (7): [PMID:24900720] [10.1021/ml4000782]

6. Vignaroli G, Iovenitti G, Zamperini C, Coniglio F, Calandro P, Molinari A, Fallacara AL, Sartucci A, Calgani A, Colecchia D, Mancini A, Festuccia C, Dreassi E, Valoti M, Musumeci F, Chiariello M, Angelucci A, Botta M, Schenone S..  (2017)  Prodrugs of Pyrazolo[3,4-d]pyrimidines: From Library Synthesis to Evaluation as Potential Anticancer Agents in an Orthotopic Glioblastoma Model.,  60  (14): [PMID:28650650] [10.1021/acs.jmedchem.7b00637]

Source

Source(1):

• Scientific Literature