Compound 1195

Identifiers

Canonical SMILES:

CN1C(=O)N(C(=O)[C@]11CN(C[C@H]1c1ccc(cc1)C#N)c1ncc(s1)C(O)=O)c1cc(Cl)cc(Cl)c1

IUPAC name:

2-[(5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl]-1,3-thiazole-5-carboxylic acid

InChi:

InChI=1S/C24H17Cl2N5O4S/c1-29-23(35)31(17-7-15(25)6-16(26)8-17)21(34)24(29)12-30(22-28-10-19(36-22)20(32)33)11-18(24)14-4-2-13(9-27)3-5-14/h2-8,10,18H,11-12H2,1H3,(H,32,33)/t18-,24+/m0/s1

InChiKey:
```
BFZWHXBQAYWTFR-MHECFPHRSA-N
```

External links

46220964

CHEMBL1096088

24677818

External search

Bibliography (1)

Publication	Name
Watterson SH, Xiao Z, Dodd DS, Tortolani DR, Vaccaro W, Potin D, Launay M, Stetsko DK, Skala S, Davis PM, Lee D, Yang X, McIntyre KW, Balimane P, Patel K, Yang Z, Marathe P, Kadiyala P, Tebben AJ, Sheriff S, Chang CY, Ziemba T, Zhang H, Chen BC, DelMonte AJ, Aranibar N, McKinnon M, Barrish JC, Suchard SJ, Murali Dhar TG. . Small molecule antagonist of leukocyte function associated antigen-1 (LFA-1): structure-activity relationships leading to the identification of 6-((5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl)nicotinic acid (BMS-688521). Journal of medicinal chemistry.	2p

Publication

Name

Watterson SH, Xiao Z, Dodd DS, Tortolani DR, Vaccaro W, Potin D, Launay M, Stetsko DK, Skala S, Davis PM, Lee D, Yang X, McIntyre KW, Balimane P, Patel K, Yang Z, Marathe P, Kadiyala P, Tebben AJ, Sheriff S, Chang CY, Ziemba T, Zhang H, Chen BC, DelMonte AJ, Aranibar N, McKinnon M, Barrish JC, Suchard SJ, Murali Dhar TG. . Small molecule antagonist of leukocyte function associated antigen-1 (LFA-1): structure-activity relationships leading to the identification of 6-((5S,9R)-9-(4-cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]nonan-7-yl)nicotinic acid (BMS-688521). Journal of medicinal chemistry.

Pharmacological data

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

Targets

PPI family	Best activity	Diseases	MMoA
LFA / ICAM	8.30	immune system disease	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	541.04 g/mol
HBA	9
HBD	1
HBA + HBD	10
AlogP	4.55
TPSA	117.84
RB	4

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	1	0	0	0

Pharmacological data

Bibliography	Name	Target	Competition	Assay type	Assay name	Cell line	Activity type	Activity
20405922	2p	ITAL P20701		Biochemical assay	ELISA		pIC50 (half maximal inhibitory concentration, -log10)	8.30

Ta	Name	Drugbank ID
0.4826	Degarelix	DB06699
0.4221	BMS-564929	DB07286
0.4213	Mosapramine	DB13676
0.4192	1-(5-{2-[(1-methyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl)amino]ethyl}-1,3-thiazol-2-yl)-3-[3-(trifluoromethyl)phenyl]urea	DB07362
0.4189	SAR-405838	DB12541
0.4185	Olcegepant	DB04869
0.4181	Dasatinib	DB01254
0.4158	SNS-314	DB06134
0.4135	GI-181771X	DB12309
0.4111	N-[2-methyl-5-(methylcarbamoyl)phenyl]-2-{[(1R)-1-methylpropyl]amino}-1,3-thiazole-5-carboxamide	DB06991
0.4108	4-Amino-2-[(3-chlorophenyl)amino]-5-(4-fluorobenzoyl)-1,3-thiazol-3-ium	DB07489
0.4040	Cobicistat	DB09065
0.4021	1-{5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-1,3-thiazol-2-yl}-3-[3-(trifluoromethyl)phenyl]urea	DB07360
0.4007	(S)-2-CHLORO-N-(1-(2-(2-HYDROXYETHYLAMINO)-2-OXOETHYL)-2-OXO-1,2,3,4-TETRAHYDROQUINOLIN-3-YL)-6H-THIENO[2,3-B]PYRROLE-5-CARBOXAMIDE	DB07792
0.4000	(4R)-N-[4-({[2-(DIMETHYLAMINO)ETHYL]AMINO}CARBONYL)-1,3-THIAZOL-2-YL]-4-METHYL-1-OXO-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE-6-CARBOXAMIDE	DB07406