153624-58-9Relevant articles and documents
A ring closing metathesis-manganese dioxide oxidation sequence for the synthesis of substituted pyrroles
Keeley, Aaron,McCauley, Shane,Evans, Paul
, p. 2552 - 2559 (2016/04/26)
The combination of ring closing, or enyne metathesis with oxidation in order to prepare N-sulfonyl pyrroles is described. Reasonable to good yields were obtained for a variety of substituents and the procedure may also be conducted in one-pot. 2-Bromo N-sulfonyl adducts prepared in this manner were subjected to an intramolecular Heck-type cyclisation, forming cyclic sulfonamides.
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, Natesan,Gu, Zhengxiang,Stein, Philip D.,Bisaha, Sharon,Spergel, Steve,Girotra, Ravi,Lee, Ving G.,Lloyd, John,Misra, Raj N.,Schmidt, Joan,Mathur, Arvind,Stratton, Leslie,Kelly, Yolanda F.,Bird, Eileen,Waldron, Tom,Liu, Eddie C.-K.,Zhang, Rongan,Lee, Helen,Serafino, Randy,Abboa-Offei, Benoni,Mathers, Parker,Giancarli, Mary,Seymour, Andrea Ann,Webb, Maria L.,Moreland, Suzanne,Barrish, Joel C.,Hunt, John T.
, p. 5198 - 5218 (2007/10/03)
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 ET(A) 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 μmol/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.