TCMDC-125506

ID: ALA528696

Cas Number: 865270-61-7

PubChem CID: 4798096

Max Phase: Preclinical

Molecular Formula: C16H13ClN2

Molecular Weight: 268.75

Molecule Type: Small molecule

Names and Identifiers

Synonyms: TCMDC-125506 | TCMDC-125506 | N-benzyl-7-chloroquinolin-4-amine|865270-61-7|TCMDC-125506|CHEMBL528696|N-benzyl-7-chloro-quinolin-4-amine|MLS001175639|4-benzylamino-7-chloroquinoline|SCHEMBL13496121|CHEBI:116229|IMBPMAAMRHSTEU-UHFFFAOYSA-N|DTXSID301323947|HMS2904J08|4-(N-benzyl)amino-7-chloroquinoline|BDBM50233286|AKOS008922494|CCG-301676|SMR000590020|7-chloro-N-(phenylmethyl)-4-quinolinamine|CS-0231981|EN300-126041|Q27199022|Z31196920

Canonical SMILES:  Clc1ccc2c(NCc3ccccc3)ccnc2c1

Standard InChI:  InChI=1S/C16H13ClN2/c17-13-6-7-14-15(8-9-18-16(14)10-13)19-11-12-4-2-1-3-5-12/h1-10H,11H2,(H,18,19)

Standard InChI Key:  IMBPMAAMRHSTEU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    0.3941   -0.6722    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1086   -1.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1086   -1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8231   -2.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -2.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -3.1472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -3.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -4.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8231   -4.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8231   -5.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -6.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -5.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -4.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9665   -1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9665   -1.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520   -0.6722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -1.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8231   -0.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 19  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 18  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 14  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  6 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA528696

   N-benzyl-7-chloroquinolin-4-amine

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: 268.75

Molecular Weight (Monoisotopic): 268.0767

AlogP: 4.50

#Rotatable Bonds: 3

Polar Surface Area: 24.92

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.27

CX LogP: 3.93

CX LogD: 3.70

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.76

Np Likeness Score: -1.36

References

1. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

2. PubChem BioAssay data set, 

3. Rojas Ruiz FA, García-Sánchez RN, Estupiñan SV, Gómez-Barrio A, Torres Amado DF, Pérez-Solórzano BM, Nogal-Ruiz JJ, Martínez-Fernández AR, Kouznetsov VV..  (2011)  Synthesis and antimalarial activity of new heterocyclic hybrids based on chloroquine and thiazolidinone scaffolds.,  19  (15): [PMID:21723734] [10.1016/j.bmc.2011.06.025]

4. Fonseca-Berzal C, Rojas Ruiz FA, Escario JA, Kouznetsov VV, Gómez-Barrio A..  (2014)  In vitro phenotypic screening of 7-chloro-4-amino(oxy)quinoline derivatives as putative anti-Trypanosoma cruzi agents.,  24  (4): [PMID:24461296] [10.1016/j.bmcl.2013.12.071]

5. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

6. 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]

7. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

8. Willems S, Ohrndorf J, Kilu W, Heering J, Merk D..  (2021)  Fragment-like Chloroquinolineamines Activate the Orphan Nuclear Receptor Nurr1 and Elucidate Activation Mechanisms.,  64  (5.0): [PMID:33629841] [10.1021/acs.jmedchem.0c01779]

9. 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(5):

• Scientific Literature
• GSK Malaria Screening
• PubChem BioAssays
• St Jude Leishmania Screening
• Winzeler Lab Plasmodium Screening Data