25031-03-2

Upstream product

• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 95477-89-7 (2S,5R,6R)-6-((Z)-2-Methoxycarbonyl-1-methyl-vinylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 
• 551-16-6 6-Aminopenicillanic Acid 
• 18997-19-8 Chloromethyl pivalate 
• 104-15-4 toluene-4-sulfonic acid 
• 25031-06-5 (pivaloyloxy)methyl 6β-aminopenicillanate hydrochloride 
• 87106-40-9 triethylammonium 6β-(1-methyl-2-methoxycarbonylvinylamino)penicillanate 

Downstream Products

• 55138-82-4 pivampicillin hydrochloride 
• 1584803-99-5 [(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(4-nitrophenyl)amino]-penicillanate 
• 1584804-01-2 [(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-{[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]amino}penicillanate 
• 1584804-02-3 [(2,2-dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-{[(4-nitrophenyl)sulfonyl]amino}penicillanate 
• 1415712-79-6 C₃₀H₄₅N₃O₁₂S₂ 
• 1415712-81-0 C₃₀H₄₅N₃O₁₄S₂ 
• 1415712-69-4 pivaloyloxymethyl 1,1-dioxide-6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate 
• 1415712-86-5 C₂₄H₄₃N₃O₁₃S₂*C₇H₈O₃S 
• 1415712-84-3 C₂₂H₃₉N₃O₁₂S₂*C₇H₈O₃S 
• 1415712-82-1 C₃₂H₄₉N₃O₁₅S₂ 
• 1415712-67-2 pivaloyloxymethyl 6-β-[(benzyloxycarbonyl)methylsulfonamido]penicillinate 

Relevant academic research and scientific papers

Synthesis and characterisation of a new podand based on a calixarene and a β-lactam

Two penicillin arms have been grafted at the lower rim of the p-tert-butylcalix[4]arene, giving a new kind of podand which was fully characterised.

Attachment of a styryl group to the 6-position of a protected penicillanic acid via cobaloxime-mediated radical alkyl-alkenyl cross coupling

Cobaloxime-catalyzed cross coupling of styrene with 6α-bromopenicillanic acid pivalolyl-oxymethyl ester (4) introduces a styryl group into the 6 position of the penicillanic acid nucleus. The method should be capable of introducing a variety of aryl-substituted alkenes into the 6 position. Such compounds may be useful as novel β-lactam antibiotics/β-lactamase inhibitors.

Synthesis of some heterofunctionalized penicillanic acid derivatives and investigation of their Biological Activities

6-Substituted amino-penicillanic acid esters were synthesized starting with 6-apa. The compounds containing a 1,3-thiazole- or 1,3-thiazolidinone nucleus linked to the penicillanic acid skeleton via a hydrazino linkage were obtained from 6-apa. The treatment of carbonylamino and carbonothioylamino compounds with 4-chlorophenacyl bromide or ethyl bromoacetate gave 6-bis{4-[1,3- thiazol(idinone)amino]benzoyl}amino derivatives of 6-apa. Benzyl derivatives were synthesized in several steps, starting with 4-aminobenzoyl chloride. The treatment of 4-{[3-benzyl-4-oxo-1,3-thia(oxa)zolidin-2-ylidene]amino}benzoyl chlorides with 6-apa in ethanolic solution produced the 6-[bis(4-{[3-benzyl-4- oxo-1,3-thiazolidin-2-ylidene]amino}benzoyl)amino] derivative of penicillanic acid, while the reaction of the same intermediates in DMF gave the mono-substituted amino derivative of 6-apa. The synthesized compounds were screened for their biological activities, and some of them were found to possess good to moderate antimicrobial activity. Moreover, some of the compounds displayed antiurease, anti-β-lactamase, and/or antilipase activities. Synthesis of some penicillanic acid derivatives including several heterocyclic rings was performed and the biological activities of the synthesized compounds were investigated. Some of them were found to possess antimicrobial, anti-β-lactamase, antiurease, and/or antilipase activity.