188249-92-5

Upstream product

• 182750-65-8 benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate 
• 7440-44-0 pyrographite 
• 80353-26-0 6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide 
• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 
• 24138-28-1 6-bromopenicillanic acid 
• 182750-64-7 benzhydryl 2β-(chloroacetoxy)methyl-1,1-dioxo-penicillanate 

Downstream Products

• 188250-29-5 diphenylmethyl (2S,3R,5R)-3-(acetylhydrazono)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-21-7 diphenylmethyl (2S,3R,5R)-3-(t-butoxycarbonylmethoxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-17-1 diphenylmethyl (2S,3R,5R)-3-(cyclopropylmethoxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 182750-66-9 (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester 
• 1026477-53-1 (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 757167-94-5 diphenylmethyl (2S,3R,5R)-3-(carbamoylmethoxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-02-4 diphenylmethyl (2S,3R,5R)-3-[(2-hydroxyethoxy)imino]methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-33-1 diphenylmethyl (2S,3R,5R)-3-(benzoylhydrazono)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-40-0 diphenylmethyl (2S,3R,5R)-3-(benzyloxycarbonylhydrazono)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-38-6 diphenylmethyl (2S,3R,5R)-3-methyl-4,4,7-trioxo-3-(thiosemicarbazono)methyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-10-4 diphenylmethyl (2S,3R,5R)-3-(t-butoxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188250-00-2 diphenylmethyl (2S,3R,5R)-3-(ethoxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 188249-93-6 diphenylmethyl (2S,3R,5R)-3-(methoxyimino)methyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 

Relevant academic research and scientific papers

Crystal structures of KPC-2 β-lactamase in complex with 3-nitrophenyl boronic acid and the penam sulfone PSR-3-226

Class A carbapenemases are a major threat to the potency of carbapenem antibiotics. A widespread carbapenemase, KPC-2, is not easily inhibited by β-lactamase inhibitors (i.e., clavulanic acid, sulbactam, and tazobactam). To explore different mechanisms of inhibition of KPC-2, we determined the crystal structures of KPC-2 with two β-lactamase inhibitors that follow different inactivation pathways and kinetics. The first complex is that of a small boronic acid compound, 3-nitrophenyl boronic acid (3-NPBA), bound to KPC-2 with 1.62-A resolution. 3-NPBA demonstrated a Km value of 1.0±0.1 μM (mean±standard error) for KPC-2 and blocks the active site by making a reversible covalent interaction with the catalytic S70 residue. The two boron hydroxyl atoms of 3-NPBA are positioned in the oxyanion hole and the deacylation water pocket, respectively. In addition, the aromatic ring of 3-NPBA provides an edge-to-face interaction with W105 in the active site. The structure of KPC-2 with the penam sulfone PSR-3-226 was determined at 1.26-A resolution. PSR-3-226 displayed a Km value of 3.8±0.4 μM for KPC-2, and the inactivation rate constant (k inact) was 0.034±0.003 s-1. When covalently bound to S70, PSR-3-226 forms a trans-enamine intermediate in the KPC-2 active site. The predominant active site interactions are generated via the carbonyl oxygen, which resides in the oxyanion hole, and the carboxyl moiety of PSR-3-226, which interacts with N132, N170, and E166. 3-NPBA and PSR-3-226 are the first β-lactamase inhibitors to be trapped as an acyl-enzyme complex with KPC-2. The structural and inhibitory insights gained here could aid in the design of potent KPC-2 inhibitors. Copyright

Synthesis and biological evaluation of penam sulfones as inhibitors of β-lactamases

The chemical synthesis of a series of new penam sulfone derivatives bearing a 2β-substituted-oxyimino and -hydrazone substituents, their β-lactamase inhibitory properties against selected enzymes representing class A and C β-lactamases are reported. The o

PENAM SULFONES AS BETA-LACTAMASE INHIBITORS

Novel 3-(substituted)-3-methyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate, 4,4-dioxides which are of value for use in combination with beta-lactam antibiotics to increase the effectiveness of the antibiotics