1-Benzo[1,3]dioxol-5-yl-2-[5-(3,4-dimethoxy-phenyl)-pyrimidin-2-yl]-1,2,3,9-tetrahydro-beta-carbolin-4-one

ID: ALA133285

Chembl Id: CHEMBL133285

PubChem CID: 10279632

Max Phase: Preclinical

Molecular Formula: C30H24N4O5

Molecular Weight: 520.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cnc(N3CC(=O)c4c([nH]c5ccccc45)C3c3ccc4c(c3)OCO4)nc2)cc1OC

Standard InChI:  InChI=1S/C30H24N4O5/c1-36-23-9-7-17(11-25(23)37-2)19-13-31-30(32-14-19)34-15-22(35)27-20-5-3-4-6-21(20)33-28(27)29(34)18-8-10-24-26(12-18)39-16-38-24/h3-14,29,33H,15-16H2,1-2H3

Standard InChI Key:  KMTKHFJNSNSBKT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA133285

   1-Benzo[1,3]dioxol-5-yl-2-[5-(3,4-dimethoxy-phenyl)-pyrimidin-2-yl]-1,2,3,9-tetrahydro-beta-carbolin-4-one

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: 520.55

Molecular Weight (Monoisotopic): 520.1747

AlogP: 5.16

#Rotatable Bonds: 5

Polar Surface Area: 98.80

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.32

CX Basic pKa: 0.66

CX LogP: 4.58

CX LogD: 4.58

Aromatic Rings: 5

Heavy Atoms: 39

QED Weighted: 0.34

Np Likeness Score: -0.12

References

1. Sui Z, Guan J, Macielag MJ, Jiang W, Zhang S, Qiu Y, Kraft P, Bhattacharjee S, John TM, Haynes-Johnson D, Clancy J..  (2002)  Pyrimidinylpyrroloquinolones as highly potent and selective PDE5 inhibitors for treatment of erectile dysfunction.,  45  (19): [PMID:12213052] [10.1021/jm025545d]

2. 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]

3. 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]

4. 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]

5. 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