4-(4-(3-(1H-Imidazol-1-yl)propylamino)-3-(1,3,4-oxadiazol-2-yl)-quinolin-6-yl)benzonitrile

ID: ALA4475664

PubChem CID: 153370116

Max Phase: Preclinical

Molecular Formula: C24H19N7O

Molecular Weight: 421.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2ccc3ncc(-c4nnco4)c(NCCCn4ccnc4)c3c2)cc1

Standard InChI:  InChI=1S/C24H19N7O/c25-13-17-2-4-18(5-3-17)19-6-7-22-20(12-19)23(21(14-28-22)24-30-29-16-32-24)27-8-1-10-31-11-9-26-15-31/h2-7,9,11-12,14-16H,1,8,10H2,(H,27,28)

Standard InChI Key:  RGHRCIQSZKIKQJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   40.5651  -22.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5640  -23.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2720  -23.6063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2702  -21.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9788  -22.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9796  -23.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6881  -23.6003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.3964  -23.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3917  -22.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6826  -21.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0960  -21.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8446  -22.2798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.3877  -21.6692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.9747  -20.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1765  -21.1389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.6782  -21.1468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9684  -20.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8594  -21.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8605  -21.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1535  -20.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4450  -21.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4478  -21.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1553  -22.3778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9640  -19.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2542  -19.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2498  -18.7028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.9048  -18.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6482  -17.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8309  -17.4469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.5827  -18.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7375  -20.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0291  -20.3382    0.0000 N   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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
  9 11  1  0
 10 16  1  0
 16 17  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
  1 18  1  0
 17 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
 31 32  3  0
 21 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475664

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.46

Molecular Weight (Monoisotopic): 421.1651

AlogP: 4.52

#Rotatable Bonds: 7

Polar Surface Area: 105.45

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.00

CX LogP: 2.08

CX LogD: 1.94

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.69

References

1. Kundu B, Das SK, Paul Chowdhuri S, Pal S, Sarkar D, Ghosh A, Mukherjee A, Bhattacharya D, Das BB, Talukdar A..  (2019)  Discovery and Mechanistic Study of Tailor-Made Quinoline Derivatives as Topoisomerase 1 Poison with Potent Anticancer Activity.,  62  (7): [PMID:30897325] [10.1021/acs.jmedchem.8b01938]

2. Kundu B,Sarkar D,Chowdhuri SP,Pal S,Das SK,Das BB,Talukdar A.  (2020)  Development of a metabolically stable topoisomerase I poison as anticancer agent.,  202  [PMID:32682183] [10.1016/j.ejmech.2020.112551]

Source

Source(1):

• Scientific Literature