135613-44-4

Basic information

• Product Name: <1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid, methyl ester
• Synonyms: <1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid, methyl ester
• CAS NO: 135613-44-4
• Molecular Weight: 318.413
• Mol File: 135613-44-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: <1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: <1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid, methyl ester(135613-44-4)
• EPA Substance Registry System: <1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid, methyl ester(135613-44-4)

Safety Data

• Hazardous Substances Data: 135613-44-4(Hazardous Substances Data)

Upstream product

• 135613-48-8 4-{2-[(1S,2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-butyric acid methyl ester 
• 135682-53-0 <1S-1α,2α,3α,4α>-2-<<3-(hydroxymethyl)-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid, methyl ester 
• 133027-60-8 Acetic acid (1R,2R,3R,4S)-3-(2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-benzyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl ester 
• 6630-33-7 ortho-bromobenzaldehyde 
• 66191-86-4 3-(2-bromophenyl)propanoic acid,methyl ester 
• 52221-92-8 3-(2-bromo-phenyl)-propan-1-ol 
• 102540-15-8 methyl (2E)-3-(2-bromophenyl)-2-propenoate 
• 133027-56-2 <3-(2-bromophenyl)propoxy>dimethyl(1,1,2-trimethylpropyl)silane 
• 142758-00-7 3-[2-((1S,2R,3R,4R)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-propionic acid 
• 142757-90-2 [1S-(1α,2α,3α,4α)]-2-[[3-[(Acetyloxy)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid 
• 135613-46-6 3-{2-[(1S,2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid 
• 135682-55-2 [(1R,2R,3R,4S)-3-(2-{3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-benzyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-methanol 
• 133027-57-3 [1S-(1α,2α,3α,4α)]-α-[2-[3-[[Dimethyl-(1,1,2-trimethylpropyl)silyl]oxy]propyl]phenyl]-7-oxabicyclo[2.2.1]heptane-2,3-dimethanol 
• 135613-45-5 3-{2-[(1S,2R,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-propionic acid methyl ester 

Downstream Products

• 149079-90-3 (1R,2S,3R,4S)-3-[2-(3-Methoxycarbonyl-propyl)-benzyl]-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid 
• 1025978-54-4 4-(2-{(1S,2R,3S,4R)-3-[4-(4-Cyclohexyl-butylcarbamoyl)-oxazol-2-yl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester 
• 1028302-56-8 4-(2-{(1S,2R,3S,4R)-3-[4-(4-Cyclohexyl-butylcarbamoyl)-4,5-dihydro-oxazol-2-yl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester 
• 1026878-22-7 4-(2-{(1S,2R,3S,4R)-3-[(S)-1-(4-Cyclohexyl-butylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl}-phenyl)-butyric acid methyl ester 
• 135613-37-5 <1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid 

Relevant articles and documents

Interphenylene 7-oxabicyclo[2.2.1]heptane thromboxane A2 antagonists. Semicarbazone ω-chains

A series of chiral interphenylene 7-oxabicyclo[2.2.1]heptane semicarbazones 19-26 were prepared and evaluated for their in vitro thromboxane (TxA2) antagonistic activity and in vivo duration of action. The potency of 19-26 was found to be highly dependent on the substitution pattern of the interphenylene ring and decreased in the order ortho > meta >> para. SQ 35,091 (25), [1S-(1α,2α,3α,4α)]-2-[[3-[[[(phenylamino)carbonyl]hydrazono] methyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid, was identified as a potent and long-acting TxA2 antagonist. In human platelet rich plasma SQ 35,091 inhibited arachidonic acid (800 μM) and U-46,619 (10 μM) induced aggregation with I50 values of 3 and 12 nM, respectively. In contrast, no inhibition of ADP (20 μM) induced aggregation was observed at >1000 μM. Receptor binding studies with [3H]-SQ 29,548 showed SQ 35,091 was a competitive antagonist with a K(d) value of 1.0 ± 0.1 nM in human platelet membranes. In vivo SQ 35,091 (0.2 mg/kg po) showed extended protection (T50 = 16 h) from U-46,619 (2 mg/kg iv) induced death in mice. These compounds have for the first time demonstrated that a metabolically stable interphenylene α-sidechain can be introduced into a prostanoid-like series of TxA2 antagonists with the maintenance of potent antagonistic activity.