4-(4-Methyl-piperazin-1-ylmethyl)-N-[3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide

ID: ALA56904

Chembl Id: CHEMBL56904

Cas Number: 152459-93-3

PubChem CID: 4369496

Max Phase: Preclinical

Molecular Formula: C28H29N7O

Molecular Weight: 479.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Demethyl-imatinib | CHEMBL56904|4-[(4-METHYL-1-PIPERAZINYL)METHYL]-N-[3-[[4-(3-PYRIDINYL)-2-PYRIMIDINYL]AMINO]PHENYL]-BENZAMIDE|4-[(4-METHYLPIPERAZIN-1-YL)METHYL]-N-{3-[(4-PYRIDIN-3-YLPYRIMIDIN-2-YL)AMINO]PHENYL}BENZAMIDE|Demethyl-imatinib|SCHEMBL9485|MPZ|1y57|Imatinib and nilotinib derivative 1|BDBM50290422|VCC726984|DB04739|NS00071669|Q27095476|152459-93-3|4-(4-Methyl-piperazin-1-ylmethyl)-N-[3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide

Canonical SMILES:  CN1CCN(Cc2ccc(C(=O)Nc3cccc(Nc4nccc(-c5cccnc5)n4)c3)cc2)CC1

Standard InChI:  InChI=1S/C28H29N7O/c1-34-14-16-35(17-15-34)20-21-7-9-22(10-8-21)27(36)31-24-5-2-6-25(18-24)32-28-30-13-11-26(33-28)23-4-3-12-29-19-23/h2-13,18-19H,14-17,20H2,1H3,(H,31,36)(H,30,32,33)

Standard InChI Key:  JHMBUEWQJDGKGS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA56904

   4-[(4-Methyl-1-piperazinyl)methyl]-N-[3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide

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: 479.59

Molecular Weight (Monoisotopic): 479.2434

AlogP: 4.28

#Rotatable Bonds: 7

Polar Surface Area: 86.28

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.95

CX Basic pKa: 7.84

CX LogP: 3.86

CX LogD: 3.29

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.41

Np Likeness Score: -1.72

References

1. Zimmermann J, Buchdunger E, Mett H, Meyer T, Lydon NB.  (1997)  Potent and selective inhibitors of the Abl-kinase: phenylamino-pyrimidine (PAP) derivatives,  7  (2): [10.1016/S0960-894X(96)00601-4]

2. Singh R, Masuda ES, Payan DG..  (2012)  Discovery and development of spleen tyrosine kinase (SYK) inhibitors.,  55  (8): [PMID:22257213] [10.1021/jm201271b]

3. Cui J, Fu R, Zhou LH, Chen SP, Li GW, Qian SX, Liu S..  (2013)  BCR-ABL tyrosine kinase inhibitor pharmacophore model derived from a series of phenylaminopyrimidine-based (PAP) derivatives.,  23  (8): [PMID:23473682] [10.1016/j.bmcl.2013.01.113]

4. Sun S, Fu J..  (2018)  Methyl-containing pharmaceuticals: Methylation in drug design.,  28  (20.0): [PMID:30243589] [10.1016/j.bmcl.2018.09.016]

Source

Source(1):

• Scientific Literature