ID: ALA142952

Max Phase: Preclinical

Molecular Formula: C22H20N6O2

Molecular Weight: 400.44

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-53312
Synonyms from Alternative Forms(1):

Canonical SMILES:  N=C(N)c1ccc(NC(=O)c2ccc(C(=O)Nc3ccc(C(=N)N)cc3)cc2)cc1

Standard InChI:  InChI=1S/C22H20N6O2/c23-19(24)13-5-9-17(10-6-13)27-21(29)15-1-2-16(4-3-15)22(30)28-18-11-7-14(8-12-18)20(25)26/h1-12H,(H3,23,24)(H3,25,26)(H,27,29)(H,28,30)

Standard InChI Key:  BSZRBFBSRCZEFP-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: 400.44

Molecular Weight (Monoisotopic): 400.1648

AlogP: 2.76

#Rotatable Bonds: 6

Polar Surface Area: 157.94

Molecular Species: BASE

HBA: 4

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 11.80

CX LogP: 2.00

CX LogD: -2.82

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: -0.51

References

1. Feigon J, Denny WA, Leupin W, Kearns DR..  (1984)  Interactions of antitumor drugs with natural DNA: 1H NMR study of binding mode and kinetics.,  27  (4): [PMID:6708048] [10.1021/jm00370a007]

2. Clercq ED, Dann O..  (1980)  Diaryl amidine derivatives as oncornaviral DNA polymerase inhibitors.,  23  (7): [PMID:6157024] [10.1021/jm00181a016]

3. Vanden Eynde JJ, Mayence A, Huang TL, Collins MS, Rebholz S, Walzer PD, Cushion MT..  (2004)  Novel bisbenzamidines as potential drug candidates for the treatment of Pneumocystis carinii pneumonia.,  14  (17): [PMID:15357989] [10.1016/j.bmcl.2004.06.034]

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. 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]

Source

Source(1):

• Scientific Literature