2-(1H-Imidazol-1-yl)-3-((3,4,5-trimethoxyphenyl)thio)-1H-indole

ID: ALA2313790

Chembl Id: CHEMBL2313790

Cas Number: 1416576-23-2

PubChem CID: 71546820

Max Phase: Preclinical

Molecular Formula: C20H19N3O3S

Molecular Weight: 381.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Sc2c(-n3ccnc3)[nH]c3ccccc23)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H19N3O3S/c1-24-16-10-13(11-17(25-2)18(16)26-3)27-19-14-6-4-5-7-15(14)22-20(19)23-9-8-21-12-23/h4-12,22H,1-3H3

Standard InChI Key:  AVBIIULMFIIGCG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2313790

   2-imidazol-1-yl-3-(3,4,5-trimethoxyphenyl)sulfanyl-1H-indole

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: 381.46

Molecular Weight (Monoisotopic): 381.1147

AlogP: 4.53

#Rotatable Bonds: 6

Polar Surface Area: 61.30

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.88

CX LogP: 3.64

CX LogD: 3.63

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.84

References

1. La Regina G, Bai R, Rensen WM, Di Cesare E, Coluccia A, Piscitelli F, Famiglini V, Reggio A, Nalli M, Pelliccia S, Da Pozzo E, Costa B, Granata I, Porta A, Maresca B, Soriani A, Iannitto ML, Santoni A, Li J, Miranda Cona M, Chen F, Ni Y, Brancale A, Dondio G, Vultaggio S, Varasi M, Mercurio C, Martini C, Hamel E, Lavia P, Novellino E, Silvestri R..  (2013)  Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors.,  56  (1): [PMID:23214452] [10.1021/jm3013097]

2. La Regina G, Bai R, Coluccia A, Famiglini V, Pelliccia S, Passacantilli S, Mazzoccoli C, Ruggieri V, Verrico A, Miele A, Monti L, Nalli M, Alfonsi R, Di Marcotullio L, Gulino A, Ricci B, Soriani A, Santoni A, Caraglia M, Porto S, Da Pozzo E, Martini C, Brancale A, Marinelli L, Novellino E, Vultaggio S, Varasi M, Mercurio C, Bigogno C, Dondio G, Hamel E, Lavia P, Silvestri R..  (2015)  New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer.,  58  (15): [PMID:26132075] [10.1021/acs.jmedchem.5b00310]

3. La Regina G, Bai R, Coluccia A, Famiglini V, Passacantilli S, Naccarato V, Ortar G, Mazzoccoli C, Ruggieri V, Agriesti F, Piccoli C, Tataranni T, Nalli M, Brancale A, Vultaggio S, Mercurio C, Varasi M, Saponaro C, Sergio S, Maffia M, Coluccia AML, Hamel E, Silvestri R..  (2017)  3-Aroyl-1,4-diarylpyrroles Inhibit Chronic Myeloid Leukemia Cell Growth through an Interaction with Tubulin.,  8  (5): [PMID:28523104] [10.1021/acsmedchemlett.7b00022]

Source

Source(1):

• Scientific Literature