Compound 2279

Identifiers

Canonical SMILES:

Cc1nnc2C(NC(=O)OCc3ccccc3)N=C(c3ccccc3)c3ccccc3-n12

IUPAC name:

benzyl N-{3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaen-7-yl}carbamate

InChi:

InChI=1S/C25H21N5O2/c1-17-28-29-24-23(27-25(31)32-16-18-10-4-2-5-11-18)26-22(19-12-6-3-7-13-19)20-14-8-9-15-21(20)30(17)24/h2-15,23H,16H2,1H3,(H,27,31)

InChiKey:
```
TUWDLUFFAHHNEF-UHFFFAOYSA-N
```

External links

13953710

CHEMBL2153434

WSH

External search

Bibliography (1)

Publication	Name
Chung Chun-wa, Coste Hervé, White Julia H., Mirguet Olivier, Wilde Jonathan, Gosmini Romain L., Delves Chris, Magny Sylvie M., Woodward Robert, Hughes Stephen A., Boursier Eric V., Flynn Helen, Bouillot Anne M., Bamborough Paul, Brusq Jean-Marie G., Gellibert Françoise J., Jones Emma J., Riou Alizon M., Homes Paul, Martin Sandrine L., Uings Iain J., Toum Jérôme, Clément Catherine A., Boullay Anne-Bénédicte, Grimley Rachel L., Blandel Florence M., Prinjha Rab K., Lee Kevin, Kirilovsky Jorge, Nicodeme Edwige. . Discovery and Characterization of Small Molecule Inhibitors of the BET Family Bromodomains Journal of Medicinal Chemistry.	Compound 1

Publication

Name

Chung Chun-wa, Coste Hervé, White Julia H., Mirguet Olivier, Wilde Jonathan, Gosmini Romain L., Delves Chris, Magny Sylvie M., Woodward Robert, Hughes Stephen A., Boursier Eric V., Flynn Helen, Bouillot Anne M., Bamborough Paul, Brusq Jean-Marie G., Gellibert Françoise J., Jones Emma J., Riou Alizon M., Homes Paul, Martin Sandrine L., Uings Iain J., Toum Jérôme, Clément Catherine A., Boullay Anne-Bénédicte, Grimley Rachel L., Blandel Florence M., Prinjha Rab K., Lee Kevin, Kirilovsky Jorge, Nicodeme Edwige. . Discovery and Characterization of Small Molecule Inhibitors of the BET Family Bromodomains Journal of Medicinal Chemistry.

Compound 1

Pharmacological data

Biochemical tests	Cellular tests	PK tests	Cytotoxicity tests
7	1	0	0

Targets

PPI family	Best activity	Diseases	MMoA
Bromodomain / Histone	7.81	cancer	Inhibition

Physicochemical filters

Descriptor	Lipinski's RO5	Veber	Pfizer's 3/75
MW	≤ 500 g/mol	-	-
AlogP	≤ 5	-	≤ 3
HBA	≤ 10	-	-
HBD	≤ 5	-	-
(HBA + HBD)	-	≤ 12	-
TPSA	-	≤ 140 Å²	≥ 75 Å²
RB	-	≤ 10	-

	Descriptor	Lipinski's RO5	Veber	Pfizer's 3/75
Compliance
MW	423.17 g/mol
HBA	7
HBD	1
HBA + HBD	8
AlogP	4.19
TPSA	81.40
RB	5

Radar chart

Short name	Threshold
MW	≤ 500 g/mol
AlogP	≤ 5
HBD	≤ 5
HBA	≤ 10
TPSA	≤ 140 Å²
RB	≤ 10
ArRing	≤ 4
Fsp3	≥ 0.4
R/S	≥ 1

PCA : iPPI-DB chemical space

PCA : Correlation circle

Efficiencies: iPPI-DB biplot LE versus LLE

Summary

Bibliographic ressources	Biochemical tests	Cellular tests	PK tests	Cytotoxicity tests
1	7	1	0	0

Pharmacological data

Bibliography	Name	Target	Competition	Assay type	Assay name	Cell line	Activity type	Activity
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Biochemical assay	Surface Plasmon Resonance BRD2(2)		pKd (dissociation constant, -log10)	7.27
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Biochemical assay	Surface Plasmon Resonance BRD2(1)		pKd (dissociation constant, -log10)	6.66
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Biochemical assay	FRET BRD4		pIC50 (half maximal inhibitory concentration, -log10)	7.81
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Biochemical assay	FRET BRD3		pIC50 (half maximal inhibitory concentration, -log10)	7.55
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Biochemical assay	FRET BRD2		pIC50 (half maximal inhibitory concentration, -log10)	7.52
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Biochemical assay	Isothermal Titration Calorimetry BRD2(1)		pKd (dissociation constant, -log10)	7.34
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Biochemical assay	Isothermal Titration Calorimetry BRD2(2)		pKd (dissociation constant, -log10)	7.28
10.1021/jm200108t	Compound 1	BRD2 P25440	H4 P02309	Cellular assay	Induction of ApoA1 expression by Luciferase reporter assay	HepG2 cells	pEC50 (half maximal effective concentration, -log10)	6.36

Ta	Name	Drugbank ID
0.6825	Adinazolam	DB00546
0.6330	Alprazolam	DB00404
0.6154	Triazolam	DB00897
0.6142	Nitrazolam	DB14717
0.6064	Estazolam	DB01215
0.6050	Pyrazolam	DB14718
0.6010	Clonazolam	DB14716
0.5020	Etizolam	DB09166
0.4940	Brotizolam	DB09017
0.4377	RO-6870810	DB15151
0.4305	Birabresib	DB15189
0.4252	Remimazolam	DB12404
0.4224	Midazolam	DB00683
0.3705	Balovaptan	DB14823
0.3640	Tarazepide	DB06435