17,25-diazonia-2,9-diazaheptacyclo[23.6.2.24,7.210,17.119,23.011,16.026,31]octatriaconta-1(31),4,6,10(35),11,13,15,17(34),19,21,23(38),25,27,29,32,36-hexadecaene

ID: ALA117908

Chembl Id: CHEMBL117908

Max Phase: Preclinical

Molecular Formula: C34H30N4+2

Molecular Weight: 494.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: UCL-1684

Canonical SMILES:  c1cc2cc(c1)C[n+]1ccc(c3ccccc31)NCc1ccc(cc1)CNc1cc[n+](c3ccccc13)C2

Standard InChI:  InChI=1S/C34H28N4/c1-3-10-33-29(8-1)31-16-18-37(33)23-27-6-5-7-28(20-27)24-38-19-17-32(30-9-2-4-11-34(30)38)36-22-26-14-12-25(13-15-26)21-35-31/h1-20H,21-24H2/p+2/b35-31+,36-32+

Standard InChI Key:  HZWVJPDDZQOYGA-QUTRQNJUSA-P

Alternative Forms

1. Parent:

   

   ALA117908

   ---

2. Alternative Forms:

   

   ALA117908

   UCL 1684 ditrifluoroacetate

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: 494.64

Molecular Weight (Monoisotopic): 494.2459

AlogP: 6.20

#Rotatable Bonds: ┄

Polar Surface Area: 31.82

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -2.44

CX LogD: -2.44

Aromatic Rings: 6

Heavy Atoms: 38

QED Weighted: 0.25

Np Likeness Score: 0.44

References

1. Chen JQ, Galanakis D, Ganellin CR, Dunn PM, Jenkinson DH..  (2000)  bis-Quinolinium cyclophanes: 8,14-diaza-1,7(1, 4)-diquinolinacyclotetradecaphane (UCL 1848), a highly potent and selective, nonpeptidic blocker of the apamin-sensitive Ca(2+)-activated K(+) channel.,  43  (19): [PMID:11000001] [10.1021/jm000904v]

2. Campos Rosa J, Galanakis D, Piergentili A, Bhandari K, Ganellin CR, Dunn PM, Jenkinson DH..  (2000)  Synthesis, molecular modeling, and pharmacological testing of bis-quinolinium cyclophanes: potent, non-peptidic blockers of the apamin-sensitive Ca(2+)-activated K(+) channel.,  43  (3): [PMID:10669569] [10.1021/jm9902537]

3. Rosa JC, Galanakis D, Ganellin CR, Dunn PM, Jenkinson DH..  (1998)  Bis-quinolinium cyclophanes: 6,10-diaza-3(1,3),8(1,4)-dibenzena-1,5(1,4)- diquinolinacyclodecaphane (UCL 1684), the first nanomolar, non-peptidic blocker of the apamin-sensitive Ca(2+)-activated K+ channel.,  41  (1): [PMID:9438015] [10.1021/jm970571a]

4. Galanakis D, Ganellin CR, Chen JQ, Gunasekera D, Dunn PM..  (2004)  Bis-quinolinium cyclophanes: toward a pharmacophore model for the blockade of apamin-sensitive SKCa channels in sympathetic neurons.,  14  (16): [PMID:15261276] [10.1016/j.bmcl.2004.06.011]

5. Fletcher DI, Ganellin CR, Piergentili A, Dunn PM, Jenkinson DH..  (2007)  Synthesis and pharmacological testing of polyaminoquinolines as blockers of the apamin-sensitive Ca2+-activated K+ channel (SK(Ca)).,  15  (16): [PMID:17560109] [10.1016/j.bmc.2007.05.054]

6. Gentles RG, Grant-Young K, Hu S, Huang Y, Poss MA, Andres C, Fiedler T, Knox R, Lodge N, Weaver CD, Harden DG..  (2008)  Initial SAR studies on apamin-displacing 2-aminothiazole blockers of calcium-activated small conductance potassium channels.,  18  (19): [PMID:18774291] [10.1016/j.bmcl.2008.08.023]

7. Sørensen US, Strøbaek D, Christophersen P, Hougaard C, Jensen ML, Nielsen EØ, Peters D, Teuber L..  (2008)  Synthesis and structure-activity relationship studies of 2-(N-substituted)-aminobenzimidazoles as potent negative gating modulators ofsmall conductance Ca2+-activated K+ channels.,  51  (23): [PMID:18998663] [10.1021/jm800809f]

8. Yang D, Arifhodzic L, Ganellin CR, Jenkinson DH..  (2013)  Further studies on bis-charged tetraazacyclophanes as potent inhibitors of small conductance Ca(2+)-activated K+ channels.,  63  [PMID:23685886] [10.1016/j.ejmech.2013.02.029]

Source

Source(1):

• Scientific Literature