2-[2,3']Bipyridinyl-6'-yl-1-(2,3-dihydro-benzofuran-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

ID: ALA163905

Chembl Id: CHEMBL163905

PubChem CID: 10203901

Max Phase: Preclinical

Molecular Formula: C29H24N4O

Molecular Weight: 444.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(-c2ccc(N3CCc4c([nH]c5ccccc45)C3c3ccc4c(c3)CCO4)nc2)nc1

Standard InChI:  InChI=1S/C29H24N4O/c1-2-7-25-22(5-1)23-12-15-33(27-11-9-21(18-31-27)24-6-3-4-14-30-24)29(28(23)32-25)20-8-10-26-19(17-20)13-16-34-26/h1-11,14,17-18,29,32H,12-13,15-16H2

Standard InChI Key:  WBTKLEFBLWJDCP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA163905

   2-[2,3'']Bipyridinyl-6''-yl-1-(2,3-dihydro-benzofuran-5-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

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: 444.54

Molecular Weight (Monoisotopic): 444.1950

AlogP: 5.71

#Rotatable Bonds: 3

Polar Surface Area: 54.04

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.43

CX LogP: 5.72

CX LogD: 5.72

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: -0.76

References

1. Sui Z, Guan J, Macielag MJ, Jiang W, Qiu Y, Kraft P, Bhattacharjee S, John TM, Craig E, Haynes-Johnson D, Clancy J..  (2003)  Synthesis and biological activities of novel beta-carbolines as PDE5 inhibitors.,  13  (4): [PMID:12639576] [10.1016/s0960-894x(02)01036-3]

2. Zheng H, Li L, Sun B, Gao Y, Song W, Zhao X, Gao Y, Xie Z, Zhang N, Ji J, Yuan H, Lou H..  (2018)  Design and synthesis of furyl/thineyl pyrroloquinolones based on natural alkaloid perlolyrine, lead to the discovery of potent and selective PDE5 inhibitors.,  150  [PMID:29505934] [10.1016/j.ejmech.2018.02.039]

3. Zheng H, Wu Y, Sun B, Cheng C, Qiao Y, Jiang Y, Zhao S, Xie Z, Tan J, Lou H..  (2018)  Discovery of furyl/thienyl β-carboline derivatives as potent and selective PDE5 inhibitors with excellent vasorelaxant effect.,  158  [PMID:30245400] [10.1016/j.ejmech.2018.09.028]

4. Beato A, Gori A, Boucherle B, Peuchmaur M, Haudecoeur R..  (2021)  β-Carboline as a Privileged Scaffold for Multitarget Strategies in Alzheimer's Disease Therapy.,  64  (3.0): [PMID:33528252] [10.1021/acs.jmedchem.0c01887]

Source

Source(1):

• Scientific Literature