- Synthesis of key intermediate of phosphonosulfonates (BPH-652), 1-(3-iodopropyl)-3-phenoxy benzene
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A convenient and efficient four-step synthesis of 1-(3-iodopropyl)-3-phenoxy benzene can be achieved by 3-phenoxybenzaldehyde and malonic acid in the presence of piperidine and pyridine to yield (E)-3-(3-phenoxyphenyl)-2-propenoic acid, esterification with methanol in the present of p -toluene sulfonic acid, reduction with sodium borohydride to give 3-(3-phenoxyphenyl)propan-1-ol and iodination of 3-(3-phenoxy phenyl) propan-1-ol using iodine and triphenylphosphine in the present of potassium iodide and imidazole and to afford the title compound in an overall yield of 55.6 %.
- Lu, Min,Zhou, Shuwen,Guan, Jing,Xu, Xing,Fan,Xu, Defeng
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p. 7619 - 7621
(2015/02/02)
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- ANTI-BACTERIAL COMPOSITIONS AND METHODS INCLUDING TARGETING VIRULENCE FACTORS OF STAPHYLOCOCCUS AUREUS
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This disclosure relates to compositions and methods including for the inhibition, prevention, and/or treatment of microbial infections, including infections from such pathogens as Staphylococcus aureus.
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- Phosphonosulfonates are potent, selective inhibitors of dehydrosqualene synthase and staphyloxanthin biosynthesis in staphylococcus aureus
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Staphylococcus aureus produces a golden carotenoid virulence factor called staphyloxanthin (STX), and we report here the inhibition of the enzyme, dehydrosqualene synthase (CrtM), responsible for the first committed step in STX biosynthesis. The most acti
- Song, Yongcheng,Lin, Fu-Yang,Yin, Fenglin,Hensler, Mary,Poveda, Carlos A. Rodrígues,Mukkamala, Dushyant,Cao, Rong,Wang, Hong,Morita, Craig T.,Pacanowska, Dolores González,Nizet, Victor,Oldfield, Eric
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experimental part
p. 976 - 988
(2009/12/04)
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- Inhibition of staphyloxanthin virulence factor biosynthesis in Staphylococcus aureus: In vitro, in vivo, and crystallographic results
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The gold color of Staphylococcus aureus is derived from the carotenoid staphyloxanthin, a virulence factor for the organism. Here, we report the synthesis and activity of a broad variety of staphyloxanthin biosynthesis inhibitors that inhibit the first co
- Song, Yongcheng,Liu, Chia-I.,Lin, Fu-Yang,Joo, Hwan No,Hensler, Mary,Liu, Yi-Liang,Jeng, Wen-Yih,Low, Jennifer,Liu, George Y.,Nizet, Victor,Wang, Andrew H.-J.,Oldfield, Eric
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experimental part
p. 3869 - 3880
(2009/12/28)
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- Methods of using α-phosphonosulfonate squalene synthetase inhibitors including the treatment of atherosclerosis and hypercholesterolemia
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α-Phosphonosulfonate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula STR1 wherein R2 is OR5 or R5a ; R3 and R5 are independently H, alkyl, arylalkyl, aryl or cycloalkyl; R5a is H, alkyl, arylalkyl or aryl; R4 is H, alkyl, aryl, arylalkyl, or cycloalkyl;, Z is H, halogen, lower alkyl or lower alkenyl; and R1 is a lipophilic group which contains at least 7 carbons and is alkyl, alkenyl, alkynyl, mixed alkenyl-alkynyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, cycloheteroalkyl, cycloheteroalkylalkyl; as further defined above; including pharmaceutically acceptable salts and or prodrug esters of the phosphonic (phosphinic) and/or sulfonic acids.
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- α-phosphonosulfinic squalene synthetase inhibitors
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α-Phosphonosulfinate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula STR1 wherein R2 is OR5 or R5a ; R3 and Rsu
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