1-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(4-((6-methoxyquinolin-8-yl)amino)pentyl)urea

ID: ALA3330914

PubChem CID: 118713311

Max Phase: Preclinical

Molecular Formula: C23H24ClF3N4O2

Molecular Weight: 480.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCNC(=O)Nc2ccc(Cl)c(C(F)(F)F)c2)c2ncccc2c1

Standard InChI:  InChI=1S/C23H24ClF3N4O2/c1-14(30-20-13-17(33-2)11-15-6-4-9-28-21(15)20)5-3-10-29-22(32)31-16-7-8-19(24)18(12-16)23(25,26)27/h4,6-9,11-14,30H,3,5,10H2,1-2H3,(H2,29,31,32)

Standard InChI Key:  BXBSKZULRFNFLH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    0.0599  -18.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599  -18.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876  -19.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656  -18.9346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656  -18.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876  -17.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876  -16.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656  -16.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933  -16.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933  -17.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169  -18.1078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950  -17.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3268  -18.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0503  -17.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7739  -18.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520  -17.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1838  -18.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9074  -17.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6350  -18.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6350  -18.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3172  -19.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0449  -18.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0449  -18.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3172  -17.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7644  -19.3688    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1838  -18.9346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950  -16.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4656  -15.6394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876  -15.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7528  -17.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4779  -18.0851    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7397  -16.8520    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.4611  -17.2661    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 17 26  2  0
 12 27  1  0
  8 28  1  0
 28 29  1  0
 23 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3330914

   ---

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: 480.92

Molecular Weight (Monoisotopic): 480.1540

AlogP: 6.32

#Rotatable Bonds: 8

Polar Surface Area: 75.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.35

CX Basic pKa: 4.08

CX LogP: 4.85

CX LogD: 4.85

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: -1.52

References

1. Pavić K, Perković I, Cindrić M, Pranjić M, Martin-Kleiner I, Kralj M, Schols D, Hadjipavlou-Litina D, Katsori AM, Zorc B..  (2014)  Novel semicarbazides and ureas of primaquine with bulky aryl or hydroxyalkyl substituents: synthesis, cytostatic and antioxidative activity.,  86  [PMID:25203780] [10.1016/j.ejmech.2014.09.013]

2. Levatić J, Pavić K, Perković I, Uzelac L, Ester K, Kralj M, Kaiser M, Rottmann M, Supek F, Zorc B..  (2018)  Machine learning prioritizes synthesis of primaquine ureidoamides with high antimalarial activity and attenuated cytotoxicity.,  146  [PMID:29407988] [10.1016/j.ejmech.2018.01.062]

3. Pavić K, Perković I, Pospíšilová Š, Machado M, Fontinha D, Prudêncio M, Jampilek J, Coffey A, Endersen L, Rimac H, Zorc B..  (2018)  Primaquine hybrids as promising antimycobacterial and antimalarial agents.,  143  [PMID:29220797] [10.1016/j.ejmech.2017.11.083]

Source

Source(1):

• Scientific Literature