3-Benzofuran-3-yl-N7,N7-dimethylquinoline-2,7-diamine

ID: ALA5289451

Max Phase: Preclinical

Molecular Formula: C19H17N3O

Molecular Weight: 303.37

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc2cc(-c3coc4ccccc34)c(N)nc2c1

Standard InChI:  InChI=1S/C19H17N3O/c1-22(2)13-8-7-12-9-15(19(20)21-17(12)10-13)16-11-23-18-6-4-3-5-14(16)18/h3-11H,1-2H3,(H2,20,21)

Standard InChI Key:  BNRWPSNSRVWWQK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   19.1448  -26.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1437  -27.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8517  -28.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8499  -26.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5585  -26.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5619  -27.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2743  -28.1179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9879  -27.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9845  -26.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2675  -26.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6909  -26.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6967  -28.1113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4356  -28.1164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7282  -27.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4350  -28.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4352  -26.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9801  -26.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7706  -25.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5684  -25.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8177  -24.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2702  -24.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4701  -24.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2246  -25.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
  2 13  1  0
 13 14  1  0
 13 15  1  0
 11 16  2  0
 16 17  1  0
 17 19  1  0
 18 11  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5289451

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 303.37

Molecular Weight (Monoisotopic): 303.1372

AlogP: 4.30

#Rotatable Bonds: 2

Polar Surface Area: 55.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.55

CX LogP: 3.81

CX LogD: 3.44

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.60

Np Likeness Score: -0.50

References

1. Hammill JT, Sviripa VM, Kril LM, Ortiz D, Fargo CM, Kim HS, Chen Y, Rector J, Rice AL, Domagalska MA, Begley KL, Liu C, Rangnekar VM, Dujardin JC, Watt DS, Landfear SM, Guy RK..  (2021)  Amino-Substituted 3-Aryl- and 3-Heteroarylquinolines as Potential Antileishmanial Agents.,  64  (16.0): [PMID:34355566] [10.1021/acs.jmedchem.1c00813]

Source

Source(1):

• Scientific Literature