ID: ALA249456

Max Phase: Preclinical

Molecular Formula: C22H22N4O2

Molecular Weight: 374.44

Molecule Type: Small molecule

Representations

Synonyms (1): 4,4'-(1,3-Phenylenebis(Methylene))Bis(Oxy)Dibenzimidamide
Synonyms from Alternative Forms(1):

Canonical SMILES:  N=C(N)c1ccc(OCc2cccc(COc3ccc(C(=N)N)cc3)c2)cc1

Standard InChI:  InChI=1S/C22H22N4O2/c23-21(24)17-4-8-19(9-5-17)27-13-15-2-1-3-16(12-15)14-28-20-10-6-18(7-11-20)22(25)26/h1-12H,13-14H2,(H3,23,24)(H3,25,26)

Standard InChI Key:  OHCPXJHKRQZPCL-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: 374.44

Molecular Weight (Monoisotopic): 374.1743

AlogP: 3.41

#Rotatable Bonds: 8

Polar Surface Area: 118.20

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: 12.12

CX LogP: 2.95

CX LogD: -1.87

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -0.24

References

1. 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]

2. Patrick DA, Bakunov SA, Bakunova SM, Kumar EV, Chen H, Jones SK, Wenzler T, Barzcz T, Werbovetz KA, Brun R, Tidwell RR..  (2009)  Synthesis and antiprotozoal activities of dicationic bis(phenoxymethyl)benzenes, bis(phenoxymethyl)naphthalenes, and bis(benzyloxy)naphthalenes.,  44  (9): [PMID:19409677] [10.1016/j.ejmech.2009.03.014]

3. 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]

4. 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]

5. 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