Seven-membered conjugated carbo- and heterocyclic compounds and their homoconjugated analogs and metal complexes. Synthesis, biosynthesis, structure, and reactivity

Pietra, Francesco

doi:10.1021/cr60284a002

Cited by 182 publications

(42 citation statements)

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“…Several early reviews on troponoids from fungi and plants, such as puberulonic acid and thujaplicins have been published [1,2,3,4]. The chemical synthesis of tropones and tropolones, such as nezukone, thujaplicins, -thujaplicinol, 3-methoxytropolone, and colchicines, has benn reviewed [5,6,7,8].…”

Section: Introductionmentioning

confidence: 99%

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Zhao

2007

CMC

113

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Tropone or tropolone and its derivatives (here together called troponoids) belong to a family of natural products with a seven-membered aromatic ring and various side groups. They are mainly synthesized by plants and fungi, and most troponoids play roles of antibacterial defenses in these organisms. With an increasingly severe situation of antibiotic resistant bacteria, as well as a requirement for antifungal medicines, troponoids have attracted extensive studies since they have powerful antibacterial and antifungal activity, particularly against antibiotic-resistant bacteria. In addition, many other biological activities such as antiviral, antitumor, antioxidant, anti-inflammatory, insecticidal, or enzyme inhibitor activities are associated with troponoids. After extensive studies in the 1960s-70s, interests in natural troponoids dedclined. However, chemical and biomedical studies on troponoids bloom again from the 1990s. To date great progress has been made with troponoid study in terms of identification of new natural troponoids, chemical synthesis and properties, biological activity, biosynthesis and metabolism. Particularly, bioassay-guided screening strategy and structure-activity relation-directed structure modification and drug design has resulted in the synthesis and discovery of many new derivatives. Many of them have great promise to be developed into new medicines for their potent and specific activities. This review presents the recent advances in troponoid studies and highlights multiple faceted biological activities of troponoids, as well as their relationships with chemical structures. Chemistry, biosynthesis, and production via biotechnology of troponoids are also briefly reviewed. Applications of troponoids in daily life, agriculture, medicine, and industry, and the related patents have been considered to further extend our understanding of the increasing impact of troponoids on humans.

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Section: Introductionmentioning

confidence: 99%

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Zhao

2007

CMC

113

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“…[1,3] A number of syntheses of these tropolone derivatives have been developed. Johnson et al [10] reported the first synthesis of stipitatic acid 5 and puberulic acid 7.…”

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confidence: 99%

“…Formation of Ethyl 2,4,11,12-Tetraoxatricyclo[5.3.2.0 1,5 ]-dodeca-5,9-diene-8-carboxylate (14): Ethyl 6H-cyclohepta[d][1,3]dioxole-6-carboxylate (9) (208 mg, 1.00 mmol) and tetraphenylporphyrin (10 mg) were dissolved in 25 mL of CCl 4 . The solution was then irradiated with a projection lamp (500 W) while a slow stream of dry oxygen was passed through the solution at room temperature.…”

mentioning

confidence: 99%

A New Method for the Synthesis of Stipitatic Acid Isomers: Photooxygenation of Ethyl 6H-Cyclohepta[d][1,3]dioxole-6-carboxylate

2001

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“…As a new candidate for such photosensitive organic chromophores based on prototropic tautomerism, we focused our interest on 2-hydroxytropone (tropolone) derivatives. Since their discovery, tropolone natural products and synthetic tropolone derivatives have attracted considerable interest due to the unique structure and properties of the tropolone ring [12,13]. Tropolone undergoes a proton tunneling from hydroxyl group to carbonyl oxygen atom [14,15].…”

Section: Introductionmentioning

confidence: 99%