BMS-187308 - CAS 153624-15-8
Catalog number: 153624-15-8
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C21H25N3O3S
Molecular Weight:
399.51
COA:
Inquire
Targets:
Endothelin Receptor
Description:
BMS-187308, a sulfonamide derivative, has been found to be an endothelin-A (ETA) antagonist that was once studied about its activity against pressor effect in rats.
Purity:
98%
Appearance:
Powder
Synonyms:
BMS-187308; BMS 187308; BMS187308; UNII-7K0YU35900; CHEMBL106684; 7K0YU35900; SCHEMBL6767698; BDBM50068674; 2-[2-amino-4-(2-methylpropyl)phenyl]-N-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide
Storage:
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
MSDS:
Inquire
Quality Standard:
In-house standard
Quantity:
Milligram-Grams
InChIKey:
OZDIAVKCLFSBME-UHFFFAOYSA-N
InChI:
InChI=1S/C21H25N3O3S/c1-13(2)11-16-9-10-17(19(22)12-16)18-7-5-6-8-20(18)28(25,26)24-21-14(3)15(4)23-27-21/h5-10,12-13,24H,11,22H2,1-4H3
Canonical SMILES:
CC1=C(ON=C1C)NS(=O)(=O)C2=CC=CC=C2C3=C(C=C(C=C3)CC(C)C)N
1.Application of structure-metabolism relationships in the identification of a selective endothelin A antagonist, BMS-193884, with favourable pharmacokinetic properties.
Humphreys WG;Obermeier MT;Barrish JC;Chong S;Marino AM;Murugesan N;Wang-Iverson D;Morrison RA Xenobiotica. 2003 Nov;33(11):1109-23.
1. Based on binding affinity, 2'-amino-N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1,1'-biphenyl]-2-sulfonamide (2) was identified as an initial lead in a programme to identify selective endothelin (ET) receptor antagonists. However, the compound was extensively metabolized in preclinical animal species and human in vitro systems due to oxidative biotransformation. 2. To optimize this structural class, the site of metabolism of 2 was determined. This allowed for focussed structure-activity and structure-metabolism studies aimed at finding more metabolically stable analogues that maintained potency. New analogues were screened for their ET binding characteristics and their stability in rat and human liver microsomes. 3. The use of the microsomal stability screen was tested by the determination of the pharmacokinetic parameters of select analogues. A good correlation was found between reduced rates of rat microsomal metabolism and reduced clearance in the rat. 4. N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide (3) was identified as an analogue with improved in vitro properties and further studies revealed that the compound had improved pharmacokinetic properties.
2.Biphenylsulfonamide endothelin antagonists: structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N- (3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1, 1'-biphenyl]-2-sulfonamide (BMS-187308).
Murugesan N;Gu Z;Stein PD;Bisaha S;Spergel S;Girotra R;Lee VG;Lloyd J;Misra RN;Schmidt J;Mathur A;Stratton L;Kelly YF;Bird E;Waldron T;Liu EC;Zhang R;Lee H;Serafino R;Abboa-Offei B;Mathers P;Giancarli M;Seymour AA;Webb ML;Hunt JT J Med Chem. 1998 Dec 17;41(26):5198-218.
Substitution at the ortho position of N-(3,4-dimethyl-5-isoxazolyl) benzenesulfonamide led to the identification of the biphenylsulfonamides as a novel series of endothelin-A (ETA) selective antagonists. Appropriate substitutions on the pendant phenyl ring led to improved binding as well as functional activity. A hydrophobic group such as isobutyl or isopropoxyl was found to be optimal at the 4'-position. Introduction of an amino group at the 2'-position also led to improved analogues. Combination of the optimal 4'-isobutyl substituent with the 2'-amino function afforded an analogue (20, BMS-187308) with improved ETA binding affinity and functional activity. Compound 20 also has good oral activity in inhibiting the pressor effect caused by an ET-1 infusion in rats. Doses of 10 and 30 micromol/kg iv 20 attenuated the pressor responses due to the administration of exogenous ET-1 to conscious monkeys, indicating that the compound inhibits the in vivo activity of endothelin-1 in nonhuman primates.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related Endothelin Receptor Products


CAS 157212-55-0 Bosentan Hydrate

Bosentan Hydrate
(CAS: 157212-55-0)

Bosentan inhibits the presser response to big ET-1 both after i.v. and oral administration, with a long duration of action and no intrinsic agonist activity.

CAS 121695-87-2 Sarafotoxin S6c

Sarafotoxin S6c
(CAS: 121695-87-2)

Sarafotoxin S6c is a highly selective ETB endothelin receptor agonist (Ki = 0.29 and 28000 nM at ETB and ETA receptors, respectively).

CAS 180384-57-0 Tezosentan

Tezosentan
(CAS: 180384-57-0)

Tezosentan, also known as RO 610612 and Veletri, is a potent dual endothelian (ETA/ETB) receptor antagonist optimized from Bosentan (B675900). It acts as a vaso...

CAS 143113-45-5 BQ-3020

BQ-3020
(CAS: 143113-45-5)

BQ-3020 is a potent and selective ETB endothelin receptor agonist (Ki = 0.18 and 970 nM at human ETB and ETA receptors, respectively).

CAS 1103522-45-7 N-Despropyl-macitentan

N-Despropyl-macitentan
(CAS: 1103522-45-7)

N-Despropyl-macitentan, an active metabolite of Macitentan, is a dual ET receptor antagonist with longer half-life than Macitentan. It has been proved to be eff...

CAS 210421-74-2 Sitaxentan sodium

Sitaxentan sodium
(CAS: 210421-74-2)

Sitaxentan sodium inhibits ET-1-induced stimulation of phosphoinositide turnover with a Ki of 0.69 nM and a pA2 of 8.0.

CAS 144602-02-8 IRL-1038

IRL-1038
(CAS: 144602-02-8)

IRL-1038 is an ETB endothelin receptor antagonist. It inhibits ETB receptor-mediated contraction of tracheal smooth muscle and guinea-pig ileal without any sign...

CAS 157380-72-8 TAK-044

TAK-044
(CAS: 157380-72-8)

Tak-044 has been found to be an endothelin receptor antagonist that was once studied against some sort of liver disorders and subarachnoid haemorrhage.

Chemical Structure

CAS 153624-15-8 BMS-187308

Quick Inquiry

Verification code

Featured Items