Natural-Product Hybrids: Design, Synthesis, and Biological Evaluation of Quinone-Annonaceous Acetogenins

Hoppen, Sabine; Emde, Ulrich; Friedrich, Thorsten; Grubert, Lutz; Koert, Ulrich

doi:10.1002/1521-3773(20000616)39:12<2099::aid-anie2099>3.0.co;2-y

Cited by 46 publications

(24 citation statements)

References 3 publications

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“…For a better understanding and also to modify the activity, two hybrids 312 and 313 were designed as probes for studies with complex I. The hybrids 312 and 313 contain the quinone portion of the natural complex I substrate ubiquinone ( 311 ) instead of the α,β‐unsaturated γ‐butyrolactone found in the original acetogenins 109a…”

Section: Synthetic Hybrid Moleculesmentioning

confidence: 99%

Natural Product Hybrids as New Leads for Drug Discovery

2003

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Natural products play an important role in the development of drugs, especially for the treatment of infections and cancer, as well as immunosuppressive compounds. However, the number of natural products is limited, whereas millions of hybrids as combinations of parts of different natural products can be prepared. This new approach seems to be very promising in the development of leads for both medicinal and agrochemical applications, as the biological activity of several new hybrids exceeds that of the parent compounds. The advantage of this concept over a combinatorial chemistry approach is the high diversity and the inherent biological activity of the hybrids.

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Section: Synthetic Hybrid Moleculesmentioning

confidence: 99%

Natural Product Hybrids as New Leads for Drug Discovery

2003

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“…To clarify the mode of action of acetogenins, Koert et al . designed quinone-mucocin 166 and quinone-squamocin D 168 in which the γ-lactone moiety was exchanged for the quinone portion of ubiquinone, the natural substrate of complex I ( Scheme 12 ) [ 47 , 48 ]. A representative synthetic pathway is given by the preparation of 166 .…”

Section: Modification Of the γ-Lactone Moietymentioning

confidence: 99%

Medicinal Chemistry of Annonaceous Acetogenins: Design, Synthesis, and Biological Evaluation of Novel Analogues

Kojima

Tanaka

2009

Molecules

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Most Annonaceous acetogenins are characterized by between one and three THF ring(s) with one or two flanking hydroxyl group(s) in the center of a C32/34 fatty acid, and the terminal carboxylic acid is combined with a 2-propanol unit to form an α,β-unsaturated γ-lactone. While many studies have addressed the properties and synthesis of natural acetogenins due to their attractive biological activities and unique structural features, a number of analogues have also been described. This review covers the design, synthesis, and biological evaluation of acetogenin analogues.

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“…The concept of synthesizing natural product hybrids and analogues, containing two different pharmacophoric subunits, has been recently devised . Currently, novel strategies are the optimization of therapies with available drugs, repurposing of medicines, developing analogs of existing drugs and the evaluation and use of chemosensitizers .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Evaluation of the Anticancer Properties of Novel Quinone Bearing Carbamyl β‐Lactam Hybrids

Payili

Yennam

Rekula

et al. 2018

Journal of Heterocyclic Chem

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This paper describes a simple and practical protocol for the direct synthesis of a series of new hybrid molecules of carbamyl β‐lactam derivatives bearing quinone moiety via [2 + 2] cycloaddition of Staudinger reaction. The β‐lactam ring is tolerating carbamylation and further leads to a variety of quinone hybrid derivatives. The structures of the compounds were characterized by IR, MS, nuclear magnetic resonance, and high‐resolution mass spectra analysis. All the new synthesized compounds were screened for their in vitro antiproliferative activity using an MTT assay analysis. Out of 14 derivatives synthesized in the current study, compounds 9h, 9k, 9i, and 9b exhibited the very good anticancer activities in B16F10 cell line.

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Natural-Product Hybrids: Design, Synthesis, and Biological Evaluation of Quinone-Annonaceous Acetogenins

Cited by 46 publications

References 3 publications

Natural Product Hybrids as New Leads for Drug Discovery

Natural Product Hybrids as New Leads for Drug Discovery

Medicinal Chemistry of Annonaceous Acetogenins: Design, Synthesis, and Biological Evaluation of Novel Analogues

Design, Synthesis, and Evaluation of the Anticancer Properties of Novel Quinone Bearing Carbamyl β‐Lactam Hybrids

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