N1-(benzo[g]quinolin-4-yl)-N4-isopropylbenzene-1,4-diamine

ID: ALA493863

Chembl Id: CHEMBL493863

Cas Number: 127136-26-9

PubChem CID: 182785

Max Phase: Preclinical

Molecular Formula: C22H21N3

Molecular Weight: 327.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: DNDI1417401 | TCMDC-123916 | GNF-Pf-1979 | TCMDC-123916 | MLS000766754|TCMDC-123916|SMR000339650|GNF-PF-1979|Benzene-1,4-diamine, N-(benzo(g)quinolin-4-yl)-N'-(propan-2-yl)-|127136-26-9|N-benzo[g]quinolin-4-yl-N'-isopropylbenzene-1,4-diamine|ChemDiv3_003545|Oprea1_458379|CHEMBL493863|cid_182785|SCHEMBL5310900|BDBM51365|DTXSID30155411|HMS1483B03|HMS2756H03|1-N-benzo[g]quinolin-4-yl-4-N-propan-2-ylbenzene-1,4-diamine|DNDI1417401|N-(Benzo(g)quinolin-4-yl)-N'-(propan-2-yl)benzene-1,4-diamine|IDI1_02Show More⌵

Canonical SMILES:  CC(C)Nc1ccc(Nc2ccnc3cc4ccccc4cc23)cc1

Standard InChI:  InChI=1S/C22H21N3/c1-15(2)24-18-7-9-19(10-8-18)25-21-11-12-23-22-14-17-6-4-3-5-16(17)13-20(21)22/h3-15,24H,1-2H3,(H,23,25)

Standard InChI Key:  ZKHLFXGNCPJHKW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA493863

   Benzene-1,4-diamine, N-(benzo(g)quinolin-4-yl)-N'-(propan-2-yl)-

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: 327.43

Molecular Weight (Monoisotopic): 327.1735

AlogP: 5.95

#Rotatable Bonds: 4

Polar Surface Area: 36.95

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.19

CX LogP: 4.81

CX LogD: 4.59

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.45

Np Likeness Score: -0.90

References

1. Ciustea M, Silverman JE, Druck Shudofsky AM, Ricciardi RP..  (2008)  Identification of non-nucleoside DNA synthesis inhibitors of vaccinia virus by high-throughput screening.,  51  (20): [PMID:18808105] [10.1021/jm800366g]

2. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

3. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

4. PubChem BioAssay data set, 

5. Meister S, Plouffe DM, Kuhen KL, Bonamy GM, Wu T, Barnes SW, Bopp SE, Borboa R, Bright AT, Che J, Cohen S, Dharia NV, Gagaring K, Gettayacamin M, Gordon P, Groessl T, Kato N, Lee MC, McNamara CW, Fidock DA, Nagle A, Nam TG, Richmond W, Roland J, Rottmann M, Zhou B, Froissard P, Glynne RJ, Mazier D, Sattabongkot J, Schultz PG, Tuntland T, Walker JR, Zhou Y, Chatterjee A, Diagana TT, Winzeler EA..  (2011)  Imaging of Plasmodium liver stages to drive next-generation antimalarial drug discovery.,  334  (6061): [PMID:22096101] [10.1126/science.1211936]

6. Melissa L. Sykes, Jonathan B. Baell, Marcel Kaiser, Eric Chatelain, Danny Ganame, Jean-Robert Ioset, Vicky M Avery. WEHI/Eskitis Trypanosoma b. brucei screening data,  [10.6019/CHEMBL2094269]

7. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

8.  (2015)  Therapeutic compounds for blocking DNA synthesis of POX viruses, 

Source

Source(7):

• Scientific Literature
• GSK Malaria Screening
• Novartis Malaria Screening
• PubChem BioAssays
• Drugs for Neglected Diseases Initiative (DNDi)
• St Jude Leishmania Screening
• BindingDB Database