ID: ALA207901

Max Phase: Preclinical

Molecular Formula: C22H17N3O2

Molecular Weight: 355.40

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C1c2ccccc2-c2c1c1ccccc1c(=O)n2CCCn1ccnc1

Standard InChI:  InChI=1S/C22H17N3O2/c26-21-17-8-3-2-7-16(17)20-19(21)15-6-1-4-9-18(15)22(27)25(20)12-5-11-24-13-10-23-14-24/h1-4,6-10,13-14H,5,11-12H2

Standard InChI Key:  GCQIGYAYYLHRGY-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: 355.40

Molecular Weight (Monoisotopic): 355.1321

AlogP: 3.50

#Rotatable Bonds: 4

Polar Surface Area: 56.89

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 6.79

CX LogP: 2.08

CX LogD: 2.02

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: -0.51

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. Nagarajan M, Morrell A, Ioanoviciu A, Antony S, Kohlhagen G, Agama K, Hollingshead M, Pommier Y, Cushman M..  (2006)  Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles.,  49  (21): [PMID:17034134] [10.1021/jm060564z]

4. 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]

5. Bakshi RP, Sang D, Morrell A, Cushman M, Shapiro TA..  (2009)  Activity of indenoisoquinolines against African trypanosomes.,  53  (1): [PMID:18824603] [10.1128/aac.00650-07]

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