153623-86-0

Basic information

• Product Name: Benzenesulfonamide, 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-
• Synonyms: 2-Bromo-N-(3,4-dimethyl-isoxazol-5-yl)-benzenesulfonamide;N-(3,4-Dimethyl-5-isoxazolyl)-2-bromobenzenesulfonamide
• CAS NO: 153623-86-0
• Molecular Formula: C11H11BrN2O3S
• Molecular Weight: 331.19
• Mol File: 153623-86-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 125 - 126 °C
• Boiling Point: 466.3±55.0 °C(Predicted)
• Density: 1.629±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzenesulfonamide, 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-(153623-86-0)
• EPA Substance Registry System: Benzenesulfonamide, 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-(153623-86-0)

Safety Data

• Hazardous Substances Data: 153623-86-0(Hazardous Substances Data)

Upstream product

• 4468-47-7 2-methyl-3-oxo-butyronitrile 
• 19947-75-2 5-amino-3,4-dimethylisoxazol 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 7440-44-0 pyrographite 

Downstream Products

• 1393601-31-4 4'-[(2-butyl-6-methyl-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1393601-32-5 4'-[(2-butyl-6-methoxy-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1393601-33-6 4'-[(2-butyl-6-chloro-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1393601-34-7 4'-[(2-butyl-6-bromo-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1393601-35-8 4'-[(2-butyl-6-fluoro-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1393601-36-9 4'-[(2-butyl-6-trifluoromethyl-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1393601-37-0 4'-[(2-butyl-6-nitro-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1247725-75-2 4'-[(1H-benzimidazol-1-yl)-methyl]-N-(3,4-dimethyl-5-isoxazolyl)-N-((2-methoxyethoxy)methyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1247725-78-5 C₃₀H₃₂N₄O₅S 
• 1247725-80-9 C₃₁H₃₄N₄O₅S 
• 1247725-81-0 C₃₂H₃₆N₄O₅S 
• 1247725-86-5 4'-[(2-methyl-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 1247725-89-8 4'-[(2-ethyl-1H-benzimidazol-1-yl)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-[1,1'-biphenyl]-2-sulfonamide 
• 153624-30-7 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide 

Relevant articles and documents

Synthesis and biological evaluation of 4′-[(benzimidazole-1-yl) methyl]biphenyl-2-sulfonamide derivatives as dual angiotensin II/endothelin A receptor antagonists

A series of 4′-[(benzimidazole-1-yl)methyl]biphenyl-2-sulfonamide derivatives (Ia-Il) were synthesized and biologically evaluated. It was found that Ig, the most active compound, antagonized both Ang II AT1 and endothelin ETA receptors (AT1 IC50 = 8.5, ETA IC50 = 8.9 nM), and was more potent than losartan in RHRs with no significant effect on heart rate. The preliminary structure-activity relationships were also discussed in the present paper.

Substituted biphenylsulfonamide endothelin antagonists

Compounds of the formula inhibit the activity of endothelin. The symbols are defined as follows: R2 and R3 are each independently (a) hydrogen; (b) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, aryloxy, aralkyl or aralkoxy, any of which may be substituted with Z1, Z2 and Z3; (c) halo; (d) hydroxyl; (e) cyano; (f) nitro; (g) -C(O)H or -C(O)R6; (h) -CO2H or -CO2R6; (i) -SH, -S(O)nR6, -S(O)m-OH, -S(O)m-OR6, -O-S(O)m-R6, -O-S(O)mOH or -O-S(O)m-OR6; (j) -Z4-NR7R8; or (k) -Z4-N(R11)-Z5-NR9R10; and the remaining symbols are as defined in the specification.

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)

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.