783-08-4Relevant articles and documents
Controlling Proton-Coupled Electron Transfer in Bioinspired Artificial Photosynthetic Relays
Odella, Emmanuel,Mora, S. Jimena,Wadsworth, Brian L.,Huynh, Mioy T.,Goings, Joshua J.,Liddell, Paul A.,Groy, Thomas L.,Gervaldo, Miguel,Sereno, Leónides E.,Gust, Devens,Moore, Thomas A.,Moore, Gary F.,Hammes-Schiffer, Sharon,Moore, Ana L.
, p. 15450 - 15460 (2018)
Bioinspired constructs consisting of benzimidazole-phenol moieties bearing N-phenylimines as proton-accepting substituents have been designed to mimic the H-bond network associated with the TyrZ-His190 redox relay in photosystem II. These compo
Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D)
Romero, Eugénie,Oueslati, Saoussen,Benchekroun, Mohamed,D'Hollander, Agathe C.A.,Ventre, Sandrine,Vijayakumar, Kamsana,Minard, Corinne,Exilie, Cynthia,Tlili, Linda,Retailleau, Pascal,Zavala, Agustin,Elisée, Eddy,Selwa, Edithe,Nguyen, Laetitia A.,Pruvost, Alain,Naas, Thierry,Iorga, Bogdan I.,Dodd, Robert H.,Cariou, Kevin
supporting information, (2021/04/19)
The occurrence of resistances in Gram negative bacteria is steadily increasing to reach extremely worrying levels and one of the main causes of resistance is the massive spread of very efficient β-lactamases which render most β-lactam antibiotics useless. Herein, we report the development of a series of imino-analogues of β-lactams (namely azetidinimines) as efficient non-covalent inhibitors of β-lactamases. Despite the structural and mechanistic differences between serine-β-lactamases KPC-2 and OXA-48 and metallo-β-lactamase NDM-1, all three enzymes can be inhibited at a submicromolar level by compound 7dfm, which can also repotentiate imipenem against a resistant strain of Escherichia coli expressing NDM-1. We show that 7dfm can efficiently inhibit not only the three main clinically-relevant carbapenemases of Ambler classes A (KPC-2), B (NDM-1) and D (OXA-48) with Ki's below 0.3 μM, but also the cephalosporinase CMY-2 (class C, 86% inhibition at 10 μM). Our results pave the way for the development of a new structurally original family of non-covalent broad-spectrum inhibitors of β-lactamases.
Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization
Sugimoto, Kenji,Kosuge, Shuto,Sugita, Takae,Miura, Yuka,Tsuge, Kiyoshi,Matsuya, Yuji
supporting information, p. 3981 - 3985 (2021/05/26)
A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.
