N,N-diethyl-4-phenyl-3-(1H-tetrazol-5-yl)-6-(trifluoromethyl)quinolin-2-amine

ID: ALA5287141

Max Phase: Preclinical

Molecular Formula: C21H19F3N6

Molecular Weight: 412.42

Names and Identifiers

Canonical SMILES:  CCN(CC)c1nc2ccc(C(F)(F)F)cc2c(-c2ccccc2)c1-c1nnn[nH]1

Standard InChI:  InChI=1S/C21H19F3N6/c1-3-30(4-2)20-18(19-26-28-29-27-19)17(13-8-6-5-7-9-13)15-12-14(21(22,23)24)10-11-16(15)25-20/h5-12H,3-4H2,1-2H3,(H,26,27,28,29)

Standard InChI Key:  RVTWZFXKPCJMAI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    0.3590   -1.4455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3540    0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3589   -0.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3589   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3540    1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3600    2.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3551    2.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672    2.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7842    0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860   -1.4415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009   -1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860   -2.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158   -1.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009   -2.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8704    1.0260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6776    1.1976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0901    0.4830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.1302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -0.2060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009    1.0321    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    0.6193    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
  5  4  1  0
  6  5  2  0
  6  1  1  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
  9 10  1  0
 11  9  2  0
  5 11  1  0
 12  4  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
  3 18  1  0
 19  2  1  0
 19 20  1  0
 19 21  1  0
 20 22  1  0
 21 23  1  0
 24 18  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 18  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287141

   ---

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: 412.42

Molecular Weight (Monoisotopic): 412.1623

AlogP: 4.95

#Rotatable Bonds: 5

Polar Surface Area: 70.59

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.88

CX Basic pKa: 5.23

CX LogP: 4.03

CX LogD: 3.75

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -1.45

References

1. Floresta G, Pistarà V, Amata E, Dichiara M, Marrazzo A, Prezzavento O, Rescifina A..  (2017)  Adipocyte fatty acid binding protein 4 (FABP4) inhibitors. A comprehensive systematic review.,  138  [PMID:28738306] [10.1016/j.ejmech.2017.07.022]

2. Lehmann, Fredik F and 8 more authors.  2004-09-06  Discovery of inhibitors of human adipocyte fatty acid-binding protein, a potential type 2 diabetes target.  [PMID:15357969]

3. Barf, Tjeerd T and 9 more authors.  2009-03-15  N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors.  [PMID:19217286]

4. Hertzel, Ann V AV and 9 more authors.  2009-10-08  Identification and characterization of a small molecule inhibitor of Fatty Acid binding proteins.  [PMID:19754198]

5. Cai, Haiyan H and 5 more authors.  2010-06-15  Discovery of highly selective inhibitors of human fatty acid binding protein 4 (FABP4) by virtual screening.  [PMID:20471252]

6. Liu, Xiujie X and 10 more authors.  2011-05-15  New aromatic substituted pyrazoles as selective inhibitors of human adipocyte fatty acid-binding protein.  [PMID:21481589]

7. Zhou, Yang Y and 8 more authors.  2016-09-15  The discovery of novel and selective fatty acid binding protein 4 inhibitors by virtual screening and biological evaluation.  [PMID:27460668]

8. Kühne, Holger H and 13 more authors.  2016-10-15  Design and synthesis of selective, dual fatty acid binding protein 4 and 5 inhibitors.  [PMID:27658368]

9. Gao, Ding-Ding DD and 12 more authors.  2018-06-25  From hit to lead: Structure-based discovery of naphthalene-1-sulfonamide derivatives as potent and selective inhibitors of fatty acid binding protein 4.  [PMID:29775936]

10. Oukoloff, Killian; Lucero, Bobby; Francisco, Karol R; Brunden, Kurt R and Ballatore, Carlo.  2019-03-01  1,2,4-Triazolo[1,5-a]pyrimidines in drug design.  [PMID:30703745]

Source

Source(1):

• Scientific Literature