A-007 analogue

ID: ALA307697

Chembl Id: CHEMBL307697

Cas Number: 2675-35-6

PubChem CID: 3089902

Max Phase: Phase

Molecular Formula: C19H14N4O6

Molecular Weight: 394.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Sivifene | A-007 | Sivifene|2675-35-6|A-007|Sivifene [USAN:INN]|UNII-XAV05295I5|A007|XAV05295I5|A 007|4,4'-Dihydroxybenzophenone 2,4-dinitrophenylhydrazone|4,4'-Dihydroxybenzophenone-2,4-dinitrophenyl-hydrazone|Methanone, bis(4-hydroxyphenyl)-, (2,4-dinitrophenyl)hydrazone|4-[[2-(2,4-dinitrophenyl)hydrazinyl]-(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one|Sivifene [USAN]|Sivifene (USAN/INN)|SIVIFENE [INN]|SIVIFENE [WHO-DD]|SCHEMBL18821|CBDivE_002876|CHEMBL307697|SCHEMBL13657372|SCHEMBL136Show More⌵

Canonical SMILES:  O=[N+]([O-])c1ccc(NN=C(c2ccc(O)cc2)c2ccc(O)cc2)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C19H14N4O6/c24-15-6-1-12(2-7-15)19(13-3-8-16(25)9-4-13)21-20-17-10-5-14(22(26)27)11-18(17)23(28)29/h1-11,20,24-25H

Standard InChI Key:  YOQPCWIXYUNEET-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA307697

   SIVIFENE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.34

Molecular Weight (Monoisotopic): 394.0913

AlogP: 3.78

#Rotatable Bonds: 6

Polar Surface Area: 151.13

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.77

CX Basic pKa: 3.94

CX LogP: 5.47

CX LogD: 5.45

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -0.89

References

1. Morgan LR, Rodgers AH, LeBlanc BW, Boué SM, Yang Y, Jursic BS, Cole RB..  (2001)  Anticancer properties for 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007)/3,7-diaminophenothiazin-5-ium double salts.,  11  (16): [PMID:11514168] [10.1016/s0960-894x(01)00408-5]

2. Morgan LR, Jursic BS, Hooper CL, Neumann DM, Thangaraj K, LeBlanc B..  (2002)  Anticancer activity for 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) analogues and their abilities to interact with lymphoendothelial cell surface markers.,  12  (23): [PMID:12419372] [10.1016/s0960-894x(02)00725-4]

3. Morgan LR, Thangaraj K, LeBlanc B, Rodgers A, Wolford LT, Hooper CL, Fan D, Jursic BS..  (2003)  Design, synthesis, and anticancer properties of 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone and analogues.,  46  (21): [PMID:14521417] [10.1021/jm0301080]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Unpublished dataset, 

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. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(5):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data