D. Howard Miles

Antithrombin activity of medicinal plants from central Florida.

A chromogenic bioassay was utilized to determine the antithrombin activity of methylene chloride and methanol extracts prepared from 30 plants of central Florida. Extracts of Ardisia crenata, Tetrapanax papyriferus, Lagerstroemia indica, Callistemon lanceolatus, Antigonon Leptopus, Magnolia virginiana, and Myrica cerifera demonstrated activity of 80% or higher in this bioassay system.

Antithrombin activity of medicinal plants of the Azores.

A chromogenic bioassay was utilized to determine the antithrombin activity of methylene chloride and methanol extracts prepared from 50 plants of Azores. Extracts of the six plants Hedychium gardneranum, Tropaeolum majus, Gunnera tinctoria, Hedera helix, Festuca jubata and Laurus azorica demonstrated activity of 78% or higher in this bioassay system.

Boll weevil antifeedants from Arundo donax

Abstract Triacontanol, tricin and tetramethyl- N,N -bis(2,6-dimethylphenyl)cyclobutane-1,3-diimine, newly reported from Arundo donax , showed significant antifeedant activity against the boll weevil, Anthonomus grandis . A common mixture of phytosterols was also obtained from the aerial parts of the plant, but none showed any antifeedant activity.

Long chain aliphatic alcohols and saturated carboxylic acids from heartwood of Rhizophora apiculata

Abstract Five long chain aliphatic alcohols, 11 long chain aliphatic saturated carboxylic acids, three steroids, 2,6-dimethoxy-p-benzoquinone, syringaldehyde and sitosteryl 3-glucoside were isolated from the heartwood of Rhizophora apiculata and subsequently bioassayed for boll weevil antifeedant, antifungal and antimicrobial activity. While 2,6-dimethoxy-p-benzoquinone is the only constituent which exhibited activity, it is significant that this compound was active against fungi, bacteria and boll weevils.

3′-formyl-2′,4′,6′-trihydroxydihydrochalcone from Psidium acutangulum

Abstract Twig and leaf extracts of the Peruvian plant Psidium acutangulum were shown to have antifungal properties against the fungi Rhizoctonia solani, Helminthosporium teres and Pythium ultimum . Chemical investigation of these extracts resulted in the isolation of the new compound, 3′-formyl-2′,4′,6′-trihydroxychalcone, which demonstrated activity against the fungi R. solani and H. teres .

Treatment of breast cancer

The disclosure describes the use of one or more compounds that fall within the scope of one or more of structural formulae I, II, III, IV, V, or VI for treating triple negative breast Compounds useful for treating breast cancer include those compounds of formulae I, II, III, IV, V, or VI that inhibit proliferation of breast cancer cells and/or lead to the death of breast cancer cells, especially triple negative breast cancer.

Copper(I)-Catalyzed Cycloaddition of Methyl O-Propargylpodocarpate and Azides at Room Temperature

Abstract Copper iodide was employed as an efficient catalyst for the synthesis of 1,2,3-triazole derivatives of podocarpic acid at room temperature through “click” chemistry cycloaddition reactions of methyl O-propargylpodocarpate and propargyl O-propargylpodocarpate with azides.

Synthesis of 5-O-methylembelin

Abstract A general synthetic route to 3-alkyl-2-hydroxy-5-methoxy-1,4-benzoquinones and the total synthesis of 5-O-methylembelin is reported based upon ring expansion of substituted cyclobutenes.

Synthesis and reactions of 2-hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester

Abstract 2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester ( 1 ) was synthesized by the reaction of pentafluoroacetophenone with dimethyl oxalate in the presence of sodium methylate. Subsequently, reactions of compound 1 with aniline, o -phenylenediamine, and o -aminophenol were investigated. In addition, the thermal cyclization of ester 1 was studied and led to the formation of 5,6,8-trifluoro-7-methoxy-4-oxo-4H-chromene-2-carboxylic acid methyl ester ( 6 ) due to nucleophilic substitution of the 3-fluoro group. Hydrolysis of compound 1 and subsequent cyclization by treatment with SOCl 2 gave 5-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-furan-2,3-dione ( 3 ). Thermal decarbonylation of compound 3 under mild conditions resulted in the formation of 3-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-propene-1,3-dione ( 4 ) which dimerized to pyranone 5.

Copper-Catalyzed Cross-Coupling Reactions of Methyl 13-Iodo-O-methylpodocarpate and Amides

Abstract Copper iodide was utilized as a relatively inexpensive catalyst (versus palladium) for the high-yield synthesis of amide derivatives of podocarpic acid. The reaction involved the one-step cross-coupling reaction of methyl 13-iodo-O-methylpodocarpate with amides.