ID: ALA425544

Max Phase: Preclinical

Molecular Formula: C21H20N2O2

Molecular Weight: 332.40

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(C)CCCn1c2c(c3ccccc3c1=O)C(=O)c1ccccc1-2

Standard InChI:  InChI=1S/C21H20N2O2/c1-22(2)12-7-13-23-19-15-9-4-5-10-16(15)20(24)18(19)14-8-3-6-11-17(14)21(23)25/h3-6,8-11H,7,12-13H2,1-2H3

Standard InChI Key:  FYGFCQLVSPTQEJ-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

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: 332.40

Molecular Weight (Monoisotopic): 332.1525

AlogP: 3.16

#Rotatable Bonds: 4

Polar Surface Area: 42.31

Molecular Species: BASE

HBA: 4

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.60

CX LogP: 2.20

CX LogD: 0.97

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.23

References

1. Nagarajan M, Morrell A, Fort BC, Meckley MR, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2004)  Synthesis and anticancer activity of simplified indenoisoquinoline topoisomerase I inhibitors lacking substituents on the aromatic rings.,  47  (23): [PMID:15509164] [10.1021/jm040025z]

2. Morrell A, Antony S, Kohlhagen G, Pommier Y, Cushman M..  (2006)  Synthesis of benz[d]indeno[1,2-b]pyran-5,11-diones: versatile intermediates for the design and synthesis of topoisomerase I inhibitors.,  16  (7): [PMID:16442283] [10.1016/j.bmcl.2006.01.008]

3. Morrell A, Placzek M, Parmley S, Antony S, Dexheimer TS, Pommier Y, Cushman M..  (2007)  Nitrated indenoisoquinolines as topoisomerase I inhibitors: a systematic study and optimization.,  50  (18): [PMID:17696418] [10.1021/jm070361q]

4. Ryckebusch A, Garcin D, Lansiaux A, Goossens JF, Baldeyrou B, Houssin R, Bailly C, Hénichart JP..  (2008)  Synthesis, cytotoxicity, DNA interaction, and topoisomerase II inhibition properties of novel indeno[2,1-c]quinolin-7-one and indeno[1,2-c]isoquinolin-5,11-dione derivatives.,  51  (12): [PMID:18507368] [10.1021/jm800017u]

5. Kiselev E, DeGuire S, Morrell A, Agama K, Dexheimer TS, Pommier Y, Cushman M..  (2011)  7-azaindenoisoquinolines as topoisomerase I inhibitors and potential anticancer agents.,  54  (17): [PMID:21823606] [10.1021/jm200719v]

6. Conda-Sheridan M, Park EJ, Beck DE, Reddy PV, Nguyen TX, Hu B, Chen L, White JJ, van Breemen RB, Pezzuto JM, Cushman M..  (2013)  Design, synthesis, and biological evaluation of indenoisoquinoline rexinoids with chemopreventive potential.,  56  (6): [PMID:23472886] [10.1021/jm400026k]

7. Beck DE, Reddy PV, Lv W, Abdelmalak M, Tender GS, Lopez S, Agama K, Marchand C, Pommier Y, Cushman M..  (2016)  Investigation of the Structure-Activity Relationships of Aza-A-Ring Indenoisoquinoline Topoisomerase I Poisons.,  59  (8): [PMID:27070999] [10.1021/acs.jmedchem.6b00003]

Source

Source(1):

• Scientific Literature