3-(5-Chloro-2-furoyl)-3,7-diazabicyclo[3.3.0]octane

ID: ALA2179529

Chembl Id: CHEMBL2179529

Cas Number: 1025007-04-8

PubChem CID: 24795080

Max Phase: Phase

Molecular Formula: C11H13ClN2O2

Molecular Weight: 240.69

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Azd 1446 | Azd1446 | Azd1446 free base | AZD-1446 | AZD1446 HCL | TC-6683 | TC6683 | TC6683 HCL | CHEMBL2179529|1025007-04-8|AZD 1446;3-(5-Chloro-2-furoyl)-3,7-diazabicyclo[3.3.0]octane|(5-Chlorofuran-2-yl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone|TC 6683|AZD1446 free base|AZD1446|TC-6683, AZD1446|starbld0003294|SCHEMBL584395|BDBM50397890|AKOS015555024|KG-0039|2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl-(5-chlorofuran-2-yl)methanone

Canonical SMILES:  O=C(c1ccc(Cl)o1)N1CC2CNCC2C1

Standard InChI:  InChI=1S/C11H13ClN2O2/c12-10-2-1-9(16-10)11(15)14-5-7-3-13-4-8(7)6-14/h1-2,7-8,13H,3-6H2

Standard InChI Key:  GTUIQNHJSXQMKW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2179529

   AZD1446

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: 240.69

Molecular Weight (Monoisotopic): 240.0666

AlogP: 1.22

#Rotatable Bonds: 1

Polar Surface Area: 45.48

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.17

CX LogP: -0.16

CX LogD: -3.29

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.80

Np Likeness Score: -1.25

References

1. Mazurov AA, Miao L, Bhatti BS, Strachan JP, Akireddy S, Murthy S, Kombo D, Xiao YD, Hammond P, Zhang J, Hauser TA, Jordan KG, Miller CH, Speake JD, Gatto GJ, Yohannes D..  (2012)  Discovery of 3-(5-chloro-2-furoyl)-3,7-diazabicyclo[3.3.0]octane (TC-6683, AZD1446), a novel highly selective α4β2 nicotinic acetylcholine receptor agonist for the treatment of cognitive disorders.,  55  (21): [PMID:22793665] [10.1021/jm3006542]

2. Mazurov AA, Kombo DC, Akireddy S, Murthy S, Hauser TA, Jordan KG, Gatto GJ, Yohannes D..  (2013)  Novel nicotinic acetylcholine receptor agonists containing carbonyl moiety as a hydrogen bond acceptor.,  23  (13): [PMID:23692872] [10.1016/j.bmcl.2013.04.058]

3. Unpublished dataset, 

4.  (2014)  Nicotinic acetylcholine receptor sub-type selective amides of diazabicycloalkanes, 

5. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

6. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

7. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

8. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(5):

• Scientific Literature
• Clinical Candidates
• BindingDB Database
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6