4-(2,6-Difluoro-benzoylamino)-1H-pyrazole-3-carboxylic Acid(4-Fluoro-phenyl)-amide

ID: ALA518383

Chembl Id: CHEMBL518383

PubChem CID: 24864079

Max Phase: Preclinical

Molecular Formula: C17H11F3N4O2

Molecular Weight: 360.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(F)cc1)c1n[nH]cc1NC(=O)c1c(F)cccc1F

Standard InChI:  InChI=1S/C17H11F3N4O2/c18-9-4-6-10(7-5-9)22-17(26)15-13(8-21-24-15)23-16(25)14-11(19)2-1-3-12(14)20/h1-8H,(H,21,24)(H,22,26)(H,23,25)

Standard InChI Key:  BDRDBXXWQDFXEC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA518383

   {[(2,6-difluorophenyl)carbonyl]amino}-N-(4-fluorophenyl)-1H-pyrazole-3-carboxamide

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: 360.30

Molecular Weight (Monoisotopic): 360.0834

AlogP: 3.33

#Rotatable Bonds: 4

Polar Surface Area: 86.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.29

CX Basic pKa: ┄

CX LogP: 3.28

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -1.91

References

1. Wyatt PG, Woodhead AJ, Berdini V, Boulstridge JA, Carr MG, Cross DM, Davis DJ, Devine LA, Early TR, Feltell RE, Lewis EJ, McMenamin RL, Navarro EF, O'Brien MA, O'Reilly M, Reule M, Saxty G, Seavers LC, Smith DM, Squires MS, Trewartha G, Walker MT, Woolford AJ..  (2008)  Identification of N-(4-piperidinyl)-4-(2,6-dichlorobenzoylamino)-1H-pyrazole-3-carboxamide (AT7519), a novel cyclin dependent kinase inhibitor using fragment-based X-ray crystallography and structure based drug design.,  51  (16): [PMID:18656911] [10.1021/jm800382h]

2. Sánchez-Martínez C, Gelbert LM, Lallena MJ, de Dios A..  (2015)  Cyclin dependent kinase (CDK) inhibitors as anticancer drugs.,  25  (17): [PMID:26115571] [10.1016/j.bmcl.2015.05.100]

3. Hazlitt RA, Teitz T, Bonga JD, Fang J, Diao S, Iconaru L, Yang L, Goktug AN, Currier DG, Chen T, Rankovic Z, Min J, Zuo J..  (2018)  Development of Second-Generation CDK2 Inhibitors for the Prevention of Cisplatin-Induced Hearing Loss.,  61  (17): [PMID:30091915] [10.1021/acs.jmedchem.8b00669]

4. Cheng W, Yang Z, Wang S, Li Y, Wei H, Tian X, Kan Q..  (2019)  Recent development of CDK inhibitors: An overview of CDK/inhibitor co-crystal structures.,  164  [PMID:30639897] [10.1016/j.ejmech.2019.01.003]

5. Cheng C,Yun F,Ullah S,Yuan Q.  (2020)  Discovery of novel cyclin-dependent kinase (CDK) and histone deacetylase (HDAC) dual inhibitors with potent in vitro and in vivo anticancer activity.,  189  [PMID:31991336] [10.1016/j.ejmech.2020.112073]

6. Lin T,Li J,Liu L,Li Y,Jiang H,Chen K,Xu P,Luo C,Zhou B.  (2021)  Design, synthesis, and biological evaluation of 4-benzoylamino-1H-pyrazole-3-carboxamide derivatives as potent CDK2 inhibitors.,  215  [PMID:33611192] [10.1016/j.ejmech.2021.113281]

Source

Source(1):

• Scientific Literature