3-[(7-Chloroquinolin-4-yl)amino]propan-1-ol

ID: ALA460418

Cas Number: 60548-22-3

PubChem CID: 370995

Max Phase: Preclinical

Molecular Formula: C12H13ClN2O

Molecular Weight: 236.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCCCNc1ccnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C12H13ClN2O/c13-9-2-3-10-11(14-5-1-7-16)4-6-15-12(10)8-9/h2-4,6,8,16H,1,5,7H2,(H,14,15)

Standard InChI Key:  MCVPFDOUKZBWJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   -2.6793    1.3406    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7510    0.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503   -1.1344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931    0.1031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359    0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503   -0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359    0.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648    0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648    0.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503    1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5359   -1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6076   -0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220    0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0365   -0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0
  2 16  1  0
  3  6  1  0
  3 13  2  0
  4  7  1  0
  4 14  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  6  9  1  0
  7 11  2  0
  8 12  2  0
  9 10  2  0
 10 12  1  0
 11 13  1  0
 14 15  1  0
 15 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA460418

   1-Propanol, 3-[(7-chloro-4-quinolinyl)amino]-

2. Alternative Forms:

   

   ALA460418

   3-[(7-Chloroquinolin-4-yl)amino]propan-1-ol;hydrochloride

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: 236.70

Molecular Weight (Monoisotopic): 236.0716

AlogP: 2.68

#Rotatable Bonds: 4

Polar Surface Area: 45.15

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.31

CX LogP: 1.58

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.80

Np Likeness Score: -1.14

References

1. de Souza MV, Pais KC, Kaiser CR, Peralta MA, de L Ferreira M, Lourenço MC..  (2009)  Synthesis and in vitro antitubercular activity of a series of quinoline derivatives.,  17  (4): [PMID:19188070] [10.1016/j.bmc.2009.01.013]

2. Tukulula M, Sharma RK, Meurillon M, Mahajan A, Naran K, Warner D, Huang J, Mekonnen B, Chibale K..  (2013)  Synthesis and antiplasmodial and antimycobacterial evaluation of new nitroimidazole and nitroimidazooxazine derivatives.,  4  (1): [PMID:24900574] [10.1021/ml300362a]

3. Njogu PM, Gut J, Rosenthal PJ, Chibale K..  (2013)  Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine.,  4  (7): [PMID:24900723] [10.1021/ml400164t]

4. Braga SF, Martins LC, da Silva EB, Sales Júnior PA, Murta SM, Romanha AJ, Soh WT, Brandstetter H, Ferreira RS, de Oliveira RB..  (2017)  Synthesis and biological evaluation of potential inhibitors of the cysteine proteases cruzain and rhodesain designed by molecular simplification.,  25  (6): [PMID:28215783] [10.1016/j.bmc.2017.02.009]

5. Rocha DA, Silva EB, Fortes IS, Lopes MS, Ferreira RS, Andrade SF..  (2018)  Synthesis and structure-activity relationship studies of cruzain and rhodesain inhibitors.,  157  [PMID:30282318] [10.1016/j.ejmech.2018.08.079]

Source

Source(1):

• Scientific Literature