BMS-187308 - CAS 153624-15-8
Catalog number: 153624-15-8
Category: Inhibitor
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Endothelin Receptor
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.
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
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).
Quality Standard:
In-house standard
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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.
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CAS 153624-15-8 BMS-187308

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