Synthesis and classical pathway Complement inhibitory activity of C7-functionalized filifolinol derivatives, inspired in K-76 COOH

Larghi, Enrique L.; Operto, María A.; Torres, René; Kaufman, Teodoro S.

doi:10.1016/j.ejmech.2012.07.003

Cited by 8 publications

(1 citation statement)

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“…Several Russian patents were granted to the isolation of betulinic acid sulfate (14), disulfate and its sodium salts [191][192][193][194]. In addition, tricyclic complement inhibitor 15 was disclosed [195], as a simplified analog of the recognized inhibitor K76-COOH (16) [196][197][198][199][200].…”

Section: Low Molecular Weight Natural and Synthetic Compounds And Cyc...mentioning

confidence: 99%

Modulators of complement activation: a patent review (2008 – 2013)

Larghi¹,

Kaufman²

2014

Expert Opinion on Therapeutic Patents

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The search of specific inhibitors of the complement cascade has become one of the Holy Grails of Medicinal Chemistry for the last 30 - 40 years, with very few cases of success. Some highly specific macromolecules are currently available as modulators of the complement. However, there is still a marked need to find new, more specific, efficient and convenient alternatives, especially suited for chronic administration, including novel inexpensive small molecule inhibitors. Analogously, despite the initial success with specific monoclonal antibodies, a vast territory is awaiting to be explored and conquered, regarding the regulation of complement activation by antibody-mediated blockage of specific polypeptides or receptor sites.

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Section: Low Molecular Weight Natural and Synthetic Compounds And Cyc...mentioning

confidence: 99%

Modulators of complement activation: a patent review (2008 – 2013)

Larghi¹,

Kaufman²

2014

Expert Opinion on Therapeutic Patents

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Diastereoselective Synthesis of Spirodihydrobenzofuran Analogues of the Natural Product Filifolinol

et al. 2020

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Filifolinol is a natural occurring spirodihydrobenzofuran isolated from the resinous exudates of Heliotropium filifolium, a Chilean endemic shrub. Filifolinol and some of its derivatives have shown interesting biological activities against pathogens that attack salmonid species. Whereas the synthesis of spirodihydrobenzofurans has been limited to the use of an ortho allylphenol unit herein we report a different approach based on a C−H activation/C−O cyclization reaction for the synthesis of analogues of Filifolinol. Moreover, a diastereoselective approach was developed using the different facial preference of hydride species and organolithium compounds towards cyclic ketones.

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