Olivanic acid analogues. Part 4. Cycloaddition reactions of p-nitrobenzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, and synthesis of the 8-oxo-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate system

Bateson, John H.; Southgate, Robert; Tyler, John W.; Fell, Stephen C. M.

doi:10.1039/p19860000973

Cited by 14 publications

(3 citation statements)

References 9 publications

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“…In this context, the reduction of several 2,3-methylenepenam sulfoxides to the corresponding sulfides has been examined extensively 12 Penicilline analogues (penams) having incorporated a 2,3-methanoamino acid moiety. ,,,− …”

Section: 5 β-Lactams Containing 23-methanoamino Acid Fragmentsmentioning

confidence: 99%

“…The diastereomeric carbapenams 579a and 579b , the penam 580 , and the carbapenams 581 − 583 (Figure ) were prepared by 1,3-dipolar cycloaddition of diazomethane to the corresponding carbapenems and subsequent thermolysis of the obtained pyrazolines. − However, the biological activities of compounds 579 − 583 have not been reported so far. Derivative 583 was submitted to a mesylation−elimination sequence, furnishing the ( E )-ethylidene-substituted carbapenam 584 , which, upon ozonolysis, afforded the anhydride 585 or the acrylate 586 , depending on the reaction conditions. , …”

Section: 5 β-Lactams Containing 23-methanoamino Acid Fragmentsmentioning

confidence: 99%

“…Figure12. Penicilline analogues (penams) having incorporated a 2,3-methanoamino acid moiety 505,506,508,[510][511][512][513][514][515][516][517]. …”

mentioning

confidence: 99%

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Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids

2007

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Section: 5 β-Lactams Containing 23-methanoamino Acid Fragmentsmentioning

confidence: 99%

Section: 5 β-Lactams Containing 23-methanoamino Acid Fragmentsmentioning

confidence: 99%

See 1 more Smart Citation

Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids

2007

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α‐Unsaturated 3‐Amino‐1‐carboxymethyl‐β‐lactams as Bacterial PBP Inhibitors: Synthesis and Biochemical Assessment

Decuyper

Magdalenić

Verstraete

et al. 2019

Chemistry A European J

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Innovative monocyclic β‐lactam entities create opportunities in the battle against resistant bacteria because of their PBP acylation potential, intrinsically high β‐lactamase stability and compact scaffold. α‐Benzylidene‐substituted 3‐amino‐1‐carboxymethyl‐β‐lactams were recently shown to be potent PBP inhibitors and constitute eligible anchor points for synthetic elaboration of the chemical space around the central β‐lactam ring. The present study discloses a 12‐step synthesis of ten α‐arylmethylidenecarboxylates using a microwave‐assisted Wittig olefination as the crucial reaction step. The library was designed aiming at enhanced β‐lactam electrophilicity and extended electron flow after enzymatic attack. Additionally, increased β‐lactamase stability and intermolecular target interaction were envisioned by tackling both the substitution pattern of the aromatic ring and the β‐lactam C4‐position. The significance of α‐unsaturation was validated and the R39/PBP3 inhibitory potency shown to be augmented the most through decoration of the aromatic ring with electron‐withdrawing groups. Furthermore, ring cleavage by representative β‐lactamases was ruled out, providing new insights in the SAR landscape of monocyclic β‐lactams as eligible PBP or β‐lactamase inhibitors.

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ChemInform Abstract: Olivanic Acid Analogues. Part 4. Cycloaddition Reactions of p‐Nitrobenzyl 7‐Oxo ‐1‐ azabicyclo[3.2.0]hept‐2‐ene‐2‐carboxylate, and Synthesis of the 8‐Oxo‐ 1‐azatricyclo[4.2.0.0^2,4]octane‐2‐carboxylate System.

Bateson¹,

Southgate²,

Tyler³

et al. 1986

Chemischer Informationsdienst

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Olivanic acid analogues. Part 4. Cycloaddition reactions of p-nitrobenzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, and synthesis of the 8-oxo-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate system

Abstract: Starting from the ester (I), the polycylic azetidinone systems (III), (V), (VII), (VIII), (X) and (XI) are prepared.

Cited by 14 publications

References 9 publications

Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids

Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids

α‐Unsaturated 3‐Amino‐1‐carboxymethyl‐β‐lactams as Bacterial PBP Inhibitors: Synthesis and Biochemical Assessment

ChemInform Abstract: Olivanic Acid Analogues. Part 4. Cycloaddition Reactions of p‐Nitrobenzyl 7‐Oxo ‐1‐ azabicyclo[3.2.0]hept‐2‐ene‐2‐carboxylate, and Synthesis of the 8‐Oxo‐ 1‐azatricyclo[4.2.0.0^2,4]octane‐2‐carboxylate System.

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Olivanic acid analogues. Part 4. Cycloaddition reactions of p-nitrobenzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, and synthesis of the 8-oxo-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate system

Abstract: Starting from the ester (I), the polycylic azetidinone systems (III), (V), (VII), (VIII), (X) and (XI) are prepared.

Cited by 14 publications

References 9 publications

Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids

Natural Occurrence, Syntheses, and Applications of Cyclopropyl-Group-Containing α-Amino Acids. 1. 1-Aminocyclopropanecarboxylic Acid and Other 2,3-Methanoamino Acids

α‐Unsaturated 3‐Amino‐1‐carboxymethyl‐β‐lactams as Bacterial PBP Inhibitors: Synthesis and Biochemical Assessment

ChemInform Abstract: Olivanic Acid Analogues. Part 4. Cycloaddition Reactions of p‐Nitrobenzyl 7‐Oxo ‐1‐ azabicyclo[3.2.0]hept‐2‐ene‐2‐carboxylate, and Synthesis of the 8‐Oxo‐ 1‐azatricyclo[4.2.0.02,4]octane‐2‐carboxylate System.

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ChemInform Abstract: Olivanic Acid Analogues. Part 4. Cycloaddition Reactions of p‐Nitrobenzyl 7‐Oxo ‐1‐ azabicyclo[3.2.0]hept‐2‐ene‐2‐carboxylate, and Synthesis of the 8‐Oxo‐ 1‐azatricyclo[4.2.0.0^2,4]octane‐2‐carboxylate System.