ID: ALA269032

Max Phase: Preclinical

Molecular Formula: C19H24N6

Molecular Weight: 336.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  N=C(N)c1ccc(N2CCCN(c3ccc(C(=N)N)cc3)CC2)cc1

Standard InChI:  InChI=1S/C19H24N6/c20-18(21)14-2-6-16(7-3-14)24-10-1-11-25(13-12-24)17-8-4-15(5-9-17)19(22)23/h2-9H,1,10-13H2,(H3,20,21)(H3,22,23)

Standard InChI Key:  INGAEVQROKUCFW-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: 336.44

Molecular Weight (Monoisotopic): 336.2062

AlogP: 1.97

#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: 1.72

CX LogD: -3.11

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -0.61

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. Huang TL, Tao B, Quarshie Y, Queener SF, Donkor IO..  (2001)  N,N'-bis[4-(N-alkylamidino)phenyl]homopiperazines as anti-Pneumocystis carinii agents.,  11  (20): [PMID:11591500] [10.1016/s0960-894x(01)00541-8]

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. 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]

6. Huang TL, Mayence A, Vanden Eynde JJ..  (2014)  Some non-conventional biomolecular targets for diamidines. A short survey.,  22  (7): [PMID:24630693] [10.1016/j.bmc.2014.02.049]

7. 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]

8. Berger ML, Rebernik P..  (2015)  Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.,  25  (19): [PMID:26296478] [10.1016/j.bmcl.2015.08.017]

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