ID: ALA9126

Max Phase: Preclinical

Molecular Formula: C18H22N6

Molecular Weight: 322.42

Molecule Type: Small molecule

Representations

Canonical SMILES:  N=C(N)c1ccc(N2CCN(c3ccc(C(=N)N)cc3)CC2)cc1

Standard InChI:  InChI=1S/C18H22N6/c19-17(20)13-1-5-15(6-2-13)23-9-11-24(12-10-23)16-7-3-14(4-8-16)18(21)22/h1-8H,9-12H2,(H3,19,20)(H3,21,22)

Standard InChI Key:  GFDIGDWACCJVOI-UHFFFAOYSA-N

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

Properties

Molecular Weight: 322.42

Molecular Weight (Monoisotopic): 322.1906

AlogP: 1.58

#Rotatable Bonds: 4

Polar Surface Area: 106.22

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 12.80

CX LogP: 1.66

CX LogD: -3.17

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -0.51

References

1. Donkor IO, Huang TL, Tao B, Rattendi D, Lane S, Vargas M, Goldberg B, Bacchi C..  (2003)  Trypanocidal activity of conformationally restricted pentamidine congeners.,  46  (6): [PMID:12620080] [10.1021/jm020375q]

2. Tao B, Huang TL, Sharma TA, Reynolds IJ, Donkor IO..  (1999)  Novel bisbenzamidines and bisbenzimidazolines as noncompetitive NMDA receptor antagonists.,  9  (9): [PMID:10340618] [10.1016/s0960-894x(99)00184-5]

3. Dardonville C, Barrett MP, Brun R, Kaiser M, Tanious F, Wilson WD..  (2006)  DNA binding affinity of bisguanidine and bis(2-aminoimidazoline) derivatives with in vivo antitrypanosomal activity.,  49  (12): [PMID:16759117] [10.1021/jm060295c]

4. Cruz-Monteagudo M, Borges F, Perez González M, Cordeiro MN..  (2007)  Computational modeling tools for the design of potent antimalarial bisbenzamidines: overcoming the antimalarial potential of pentamidine.,  15  (15): [PMID:17533134] [10.1016/j.bmc.2007.05.034]

5. Vamecq J, Maurois P, Pages N, Bac P, Stables JP, Gressens P, Stanicki D, Vanden Eynde JJ..  (2010)  1,2-ethane bis-1-amino-4-benzamidine is active against several brain insult and seizure challenges through anti-NMDA mechanisms targeting the 3H-TCP binding site and antioxidant action.,  45  (7): [PMID:20427101] [10.1016/j.ejmech.2010.03.044]

6. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]

7. Vanden Eynde JJ, Mayence A, Johnson MT, Huang TL, Collins MS, Rebholz S, Walzer PD, Cushion MT, Donkor IO.  (2005)  Antitumor and Anti-Pneumocystis Carinii Activities of Novel Bisbenzamidines,  14  (3): [10.1007/s00044-005-0130-2]

8. Berger ML, Maciejewska D, Vanden Eynde JJ, Mottamal M, Żabiński J, Kaźmierczak P, Rezler M, Jarak I, Piantanida I, Karminski-Zamola G, Mayence A, Rebernik P, Kumar A, Ismail MA, Boykin DW, Huang TL..  (2015)  Pentamidine analogs as inhibitors of [(3)H]MK-801 and [(3)H]ifenprodil binding to rat brain NMDA receptors.,  23  (15): [PMID:26117647] [10.1016/j.bmc.2015.06.012]

9. Beckmann AM, Gilberg E, Gattner S, Huang TL, Vanden Eynde JJ, Mayence A, Bajorath J, Stirnberg M, Gütschow M..  (2016)  Evaluation of bisbenzamidines as inhibitors for matriptase-2.,  26  (15): [PMID:27287367] [10.1016/j.bmcl.2016.05.071]

10. Jagu E, Pomel S, Pethe S, Loiseau PM, Labruère R..  (2017)  Polyamine-based analogs and conjugates as antikinetoplastid agents.,  139  [PMID:28886510] [10.1016/j.ejmech.2017.08.014]

Source

Source(1):

• Scientific Literature