ethyl 3-amino-4-(cyclohexylamino)benzoate

ID: ALA3633556

Cas Number: 347174-05-4

PubChem CID: 4068248

Product Number: F129882, Order Now?

Max Phase: Preclinical

Molecular Formula: C15H22N2O2

Molecular Weight: 262.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(NC2CCCCC2)c(N)c1

Standard InChI:  InChI=1S/C15H22N2O2/c1-2-19-15(18)11-8-9-14(13(16)10-11)17-12-6-4-3-5-7-12/h8-10,12,17H,2-7,16H2,1H3

Standard InChI Key:  UJHBVMHOBZBWMX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9328   -3.1621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -7.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423   -8.1030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808   -8.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8787   -9.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9167  -10.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 13 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3633556

   Ferrostatin-1 (Fer-1)

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: 262.35

Molecular Weight (Monoisotopic): 262.1681

AlogP: 3.19

#Rotatable Bonds: 4

Polar Surface Area: 64.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.74

CX LogP: 2.78

CX LogD: 2.78

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: -0.77

References

1. Iniguez EA, Perez A, Maldonado RA, Skouta R..  (2015)  Novel arylalkylamine compounds exhibits potent selective antiparasitic activity against Leishmania major.,  25  (22): [PMID:26410073] [10.1016/j.bmcl.2015.09.041]

2. Hofmans S, Vanden Berghe T, Devisscher L, Hassannia B, Lyssens S, Joossens J, Van Der Veken P, Vandenabeele P, Augustyns K..  (2016)  Novel Ferroptosis Inhibitors with Improved Potency and ADME Properties.,  59  (5): [PMID:26696014] [10.1021/acs.jmedchem.5b01641]

3. Devisscher L, Van Coillie S, Hofmans S, Van Rompaey D, Goossens K, Meul E, Maes L, De Winter H, Van Der Veken P, Vandenabeele P, Berghe TV, Augustyns K..  (2018)  Discovery of Novel, Drug-Like Ferroptosis Inhibitors with in Vivo Efficacy.,  61  (22): [PMID:30354101] [10.1021/acs.jmedchem.8b01299]

4. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

5. Dodo K, Kuboki E, Shimizu T, Imamura R, Magarisawa M, Takahashi M, Tokuhiro T, Yotsumoto S, Asano K, Nakao S, Terayama N, Suda T, Tanaka M, Sodeoka M..  (2019)  Development of a Water-Soluble Indolylmaleimide Derivative IM-93 Showing Dual Inhibition of Ferroptosis and NETosis.,  10  (9): [PMID:31531196] [10.1021/acsmedchemlett.9b00142]

6. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

7. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

8. Liu J,Bandyopadhyay I,Zheng L,Khdour OM,Hecht SM.  (2020)  Antiferroptotic Activity of Phenothiazine Analogues: A Novel Therapeutic Strategy for Oxidative Stress Related Disease.,  11  (11): [PMID:33214825] [10.1021/acsmedchemlett.0c00293]

9. Yang W,Liu X,Song C,Ji S,Yang J,Liu Y,You J,Zhang J,Huang S,Cheng W,Shao Z,Li L,Yang S.  (2021)  Structure-activity relationship studies of phenothiazine derivatives as a new class of ferroptosis inhibitors together with the therapeutic effect in an ischemic stroke model.,  209  [PMID:33065375] [10.1016/j.ejmech.2020.112842]

10. Chen JN,Li T,Cheng L,Qin TS,Sun YX,Chen CT,He YZ,Liu G,Yao D,Wei Y,Li QY,Zhang GJ.  (2020)  Synthesis and in vitro anti-bladder cancer activity evaluation of quinazolinyl-arylurea derivatives.,  205  [PMID:32827851] [10.1016/j.ejmech.2020.112661]

11. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

12. Charaschanya M, Maskrey TS, LaPorte MG, Janjic JM, Wipf P..  (2022)  Synthesis and Optimization of Nitroxide-Based Inhibitors of Ferroptotic Cell Death in Cancer Cells and Macrophages.,  13  (3.0): [PMID:35300093] [10.1021/acsmedchemlett.1c00561]

13. Peng X, Tan Q, Wu L, Wu D, Xu J, Zhou H, Gu Q..  (2022)  Ferroptosis Inhibitory Aromatic Abietane Diterpenoids from Ajuga decumbens and Structural Revision of Two 3,4-Epoxy Group-Containing Abietanes.,  85  (7.0): [PMID:35796002] [10.1021/acs.jnatprod.2c00352]

14. Fang Y, Tan Q, Zhou H, Gu Q, Xu J..  (2022)  Discovery of novel diphenylbutene derivative ferroptosis inhibitors as neuroprotective agents.,  231  [PMID:35123296] [10.1016/j.ejmech.2022.114151]

15. Li Y, Shi J, Liu R, Liu Y, Liu R, Wu Z, Xu W, Ma H, Luo HB, Cheng Z..  (2023)  Structure Revisions of Phenolic Bisabolane Sesquiterpenes and a Ferroptosis Inhibitor from the Marine-Derived Fungus Aspergillus versicolor YPH93.,  86  (4): [PMID:36897077] [10.1021/acs.jnatprod.2c01022]

Source

Source(3):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6