Grignard Reagents and Their  N ‐analogues in the Synthesis of Tricyclic and Tetracyclic Cage‐like Lactams | Zendy

Tkachenko Igor V. | Zendy; Tarabara Igor N. | Zendy; Omelchenko Irina V. | Zendy; Palchykov Vitalii A. | Zendy

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Grignard Reagents and Their N ‐analogues in the Synthesis of Tricyclic and Tetracyclic Cage‐like Lactams

Author(s) -

Tkachenko Igor V.,

Tarabara Igor N.,

Omelchenko Irina V.,

Palchykov Vitalii A.

Publication year - 2018

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.3302

Subject(s) - chemistry , tricyclic , tetrahydrofuran , stereochemistry , ether , lithium (medication) , bicyclic molecule , reagent , inhibitory postsynaptic potential , lactam , stereoselectivity , combinatorial chemistry , organic chemistry , catalysis , medicine , neuroscience , solvent , biology , endocrinology

A convenient method is reported for the synthesis of 34 novel tricyclic and tetracyclic cage‐like lactams in high to excellent yields. The method involves treatment of easily available exo ‐2,3‐epoxy(or Ts‐aziridino)bicyclo[2.2.1]heptan‐ endo ‐5,6‐dicarboximides by Grignard reagents, their N ‐analogues, or phenyl lithium in tetrahydrofuran. In silico screening of biological activity spectrum showed high probability levels of glyceryl‐ether monooxygenase inhibitory, testosterone 17β‐dehydrogenase (NADP+) inhibitory, bilirubin oxidase inhibitory, and anti‐ischemic activity for tetracyclic derivatives.

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