925463-06-5

Upstream product

• 538-60-3 dibenzyl hydrogen phosphite 
• 873586-57-3 (S)-p-bromobenzenesulfinamide 

Downstream Products

• 925463-11-2 dibenzyl (R)-[1-(4'-ethoxybiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-35-0 dibenzyl (R)-2-methyl-1-[({4-[(E)-2-(4-methoxyphenyl)vinyl]phenyl}sulfonyl)amino]propylphosphonate 
• 925463-12-3 dibenzyl (R)-[1-(4'-isopropyloxybiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-13-4 dibenzyl (R)-[1-(4'-fluorobiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-18-9 dibenzyl (R)-[1-(3'-methylbiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-14-5 dibenzyl (R)-[1-(4'-chlorobiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-15-6 dibenzyl (R)-[1-(4'-methylbiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-10-1 dibenzyl (R)-[1-(4'-methoxybiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-16-7 dibenzyl (R)-[1-(3'-fluorobiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-34-9 dibenzyl (R)-2-methyl-1-[({4-[(E)-2-phenylvinyl]phenyl}sulfonyl)amino]propylphosphonate 
• 925463-17-8 dibenzyl (R)-[1-(3'-chlorobiphenyl-4-ylsulfonylamino)-2-methylpropyl]phosphonate 
• 925463-07-6 dibenzyl (R)-N-(p-bromobenzenesulfonyl)-2-amino-2-methylpropylphosphonate 

Relevant academic research and scientific papers

α-Biphenylsulfonylamino 2-methylpropyl phosphonates: Enantioselective synthesis and selective inhibition of MMPs

(R)-α-Biphenylsulfonylamino 2-methylpropyl phosphonates attain nM potency against several MMPs and are the most effective inhibitors based on phosphonate as zinc binding group. Since their preparation by direct N-acylation of expensive, enantiopure, α-aminophosphonic acids proceeds in low yields, we devised and evaluated a stereoselective and straightforward method of synthesis that avoids the unfavourable step of N-acylation. The key intermediate (R)-4-bromophenylsulfonylamino 2-methylpropyl phosphonate 9 was obtained by highly stereoselective addition of dibenzylphosphite to the enantiopure (S)-N-isobutylidene-p-bromobenzenesulfinamide 3, followed by oxidation with m-CPBA. Suzuki coupling of 9 with the desired arylboronic acids, gave the expected biphenylsulfonylamino derivatives in satisfactory yields. Liberation of the phosphonic group by hydrogenolysis led to the desired (R)-α-biphenylsulfonylamino 2-methylpropyl phosphonates 14a-i. Screening of the new compounds on MMP-1, -2, -3, -7, -8, -9, -13 and -14 showed IC50 in the range of nM in most cases.