N-[3-Methoxy-4-(2-methyl-acridin-9-ylamino)-phenyl]-methanesulfonamide

ID: ALA9821

Chembl Id: CHEMBL9821

Cas Number: 79453-36-4

PubChem CID: 154953

Max Phase: Preclinical

Molecular Formula: C22H21N3O3S

Molecular Weight: 407.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NS(C)(=O)=O)ccc1Nc1c2ccccc2nc2ccc(C)cc12

Standard InChI:  InChI=1S/C22H21N3O3S/c1-14-8-10-19-17(12-14)22(16-6-4-5-7-18(16)23-19)24-20-11-9-15(13-21(20)28-2)25-29(3,26)27/h4-13,25H,1-3H3,(H,23,24)

Standard InChI Key:  BLINWSYJRUDTKJ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA9821

   Methanesulfonanilide, 3'-methoxy-4'-((2-methyl-9-acridinyl)amino)-

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: 407.50

Molecular Weight (Monoisotopic): 407.1304

AlogP: 4.82

#Rotatable Bonds: 5

Polar Surface Area: 80.32

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.83

CX Basic pKa: 8.51

CX LogP: 3.68

CX LogD: 2.63

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: -1.26

References

1. Rewcastle GW, Atwell GJ, Baguley BC, Denny WA..  (1984)  Potential antitumor agents. 42. Structure-activity relationships for acridine-substituted dimethyl phosphoramidate derivatives of 9-anilinoacridine.,  27  (8): [PMID:6747989] [10.1021/jm00374a020]

2. Atwell GJ, Baguley BC, Finlay GJ, Rewcastle GW, Denny WA..  (1986)  Potential antitumor agents. 47. 3'-Methylamino analogues of amsacrine with in vivo solid tumor activity.,  29  (9): [PMID:3755758] [10.1021/jm00159a035]

3. Denny WA, Cain BF, Atwell GJ, Hansch C, Panthananickal A, Leo A..  (1982)  Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.,  25  (3): [PMID:7069706] [10.1021/jm00345a015]

4. Baguley BC, Denny WA, Atwell GJ, Cain BF..  (1981)  Potential antitumor agents. 35. Quantitative relationships between antitumor (L1210) potency and DNA binding for 4'-(9-acridinylamino)methanesulfon-m-anisidide analogues.,  24  (5): [PMID:6894620] [10.1021/jm00137a009]

Source

Source(1):

• Scientific Literature