Wang Qingmin

Synthesis and biological activity of novel cyanoacrylates containing ferrocenyl moiety

Abstract In a search for new herbicides with improved biological properties and different activity spectrum, we replaced phenyl moiety by ferrocenyl in cyanoacrylates, and synthesized a series of novel cyanoacrylates containing a ferrocene moiety by the reaction of aminomethylferrocene with ethoxyethyl 2-cyano-3-methylthioacrylate (or 2-cyano-3-alkoxyacrylates) in excellent yields. The title compounds were identified by IR, 1 H-NMR spectroscopy, EI MS and elemental analyses. The results of bioassay showed that some title compounds exhibit excellent herbicidal activities. In general, we found that the replacement of the phenyl with ferrocenyl in cyanoacrylates still retained excellent herbicidal activities.

Synthesis, spectroscopy and biological activity of novel acylhydrazines containing ferrocenyl moiety

Abstract In a search for new insect growth regulators, we replaced the phenyl moiety by ferrocenyl in N - tert -butyl- N , N ′-dibenzoylhydrazine and synthesized the novel N - tert -butyl- N ′-ferrocenoyl- N -substitutedbenzoylhydrazines by the reaction of ferrocenoyl chloride with N - tert -butyl- N -substituted benzoylhydrazines in dry tetrahydrofuran using triethylamine as the acid acceptor. The N - tert -butyl- N -ferrocenoyl- N ′-substituted benzoylhydrazines were prepared similarly. Then, the treatment of N - tert -butyl- N ′-ferrocenoyl- N -benzoylhydrazine with alkylmethyl(chlorosulfenyl)carbamates in the presence of sodium hydride afforded the novel acylhydrazines containing the ferrocenyl moiety. The title compounds were identified by IR spectroscopy, 1 H-NMR spectroscopy, EIMS and elemental analyses. The results of bioassay showed that some of the title compounds exhibit excellent larvicidal activities. Toxicity assays indicated that the title compounds could induce a premature, abnormal and lethal larval molt. We found by chance that one of the title compounds possesses good anti-TMV (Tobacco Mosaic Virus) activity.

Two convenient new syntheses of ferrocenoyl chloride by triphosgene

Abstract Two convenient new syntheses of ferrocenoyl chloride by triphosgene were reported. Firstly, ferrocenoyl chloride was conveniently prepared in 61.5% yield when triphosgene was reacted with ferrocene carboxylic acid in methylene dichloride at room temperature in the presence of triethylamine and DMAP. This new method for the synthesis of ferrocenoyl chloride enjoys a number of advantages in that the reaction is carried out under mild conditions and is cleaner without the formation of POCl 3 , H 3 PO 3 or SO 2 and dark-colored impurities. Secondly, ferrocene underwent reaction with one-third equivalent of triphosgene to give ferrocenoyl chloride in 38.1% yield. The main advantage of the second method for the synthesis of ferrocenoyl chloride is using cheap ferrocene as starting material.

CONDENSATION REACTION OF ß-TRIPHENYLGERMANYL PROPANOIC ACID WITH DIPHENYL α-AMINOPHOSPHONATES AND BIOACTIVITIES OF PRODUCTS

Abstract The condensation reaction of β-triphenylgermanyl propanoic acid with diphenyl α-aminophosphonates was studied. A variety of novel diphenyl N-triphenylgermanylpropiono-α-aminophosphonates were synthesized successfully in good yields by using DCC catalyzed by pyridine. The structures of all of the products were confirmed by 1HNMR, 31PNMR, IR, MS and elemental analysis. The results of bioassay showed that the new products have good anticancer activities and very strong anti-inflammatory activities.

Anti-TMV and Insecticidal Potential of Four Iridoid Glycosides from Gardenia Jasminoides Fruit

——————————— *Corresponding authors. Email: liling@jxas.ac.cn; wangqm@nankai.edu.cn Received June 13, 2018; accepted July 9, 2018. Supported by the National Natural Science Foundation of China(Nos.21562023, 21561014) and the Key Research Project of Jiangxi Province, China(No.20171BBF60074).

Synthesis of tetrahydro-β-carboline-3-carbohydrazide derivatives based on Pictet-Spengler reaction and their bioactivities

According to our previous research on the antiviral activity of β-carboline and tetrahydro-β-carboline derivatives, series of novel tetrahydro-β-carboline derivatives containing acylhydrazone moiety and different substituents at 1 position were designed, synthesized via Pictet-Spengler reaction, and evaluated for their biological activities. Most of these compounds exhibited excellent antiviral activity both in vitro and in vivo . The in vivo inactivation, curative, and protection activities of part of these compounds were much higher than that of ribavirin (36.5%, 35.2%, and 37.1% at 500 μg/mL) and harmine (40.5%, 38.6% and 42.4% at 500 μg/mL). Especially, the in vivo activities of compounds VI-1 (61.4%, 57.2%, and 68.1%) and compound VI-2 (74.5%, 69.0%, and 68.1%) at 500 μg/mL, which were nearly twofold of that of ribavirin at 500 μg/mL. At the same time, the fungicidal results showed that compound IV-2 exhibited more than 60% fungicidal activities against 5 kinds of phytopathogens. Additionally, compound IV-5 exhibited more than 60% larvicidal activity against C. pipiens pallens at 0.25 mg/kg.

Reduction of pyrimidine derivatives by LiAlH4

The reduction of ethyl 2-methylthio-(or 2-ethoxy)pyrimidine-5-carboxylate by LiAlH4 afforded ethyl 2-methylthio-(or 2-ethoxy)-1,6-dihydropyrimidine-5-carboxylate as the main product. Similarly, the reduction of 2-methylthio-(or 2-methoxy)pyrimidine-5-carboxamide by LiAlH4 gave 2-methylthio-(or 2-methoxy)-1,6-dihydropyrimidine-5-carbonitrile as main product.

Synthesis and crystal structure of 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione and 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine

AbstractThe title compound 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione has been synthesized by the reaction of 6-phenyl-1,3,5-triazine-2,4-dione with allyl bromide. Its structure was determined by X-ray single crystal diffraction. The crystal belongs to orthorhombic, space group Pbca with the following crystallographic parameters: a = 16.282(4) Å, b = 8.888(2) Å, c = 19.281(5) Å, α = 90°, β = 90°, γ = 90°, μ = 0.088 mm−1, V = 2790.1(13) Å3, z = 8, Dx = 1.282 mg/m3, F(000) = 1136, T = 293(2) K, 2.11° ≤ θ ≤ 25.02°, the final R factor: R1 = 0.0430, wR2 = 0.0981. The X-ray results demonstrate that the reaction of 6-phenyl-1,3,5-triazine-2,4-dione with allyl bromide in the presence of N,N-dimethylformamide and potassium carbonate yields the N-alkylated product. The title compound 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine has been synthesized by a new reaction, in which the solvent N,N-dimethylformamide involves. Its structure was determined by X-ray single crystal diffraction. The crystal belongs to triclinic, space group P-1 with the following crystallographic parameters: a = 7.977(2) Å, b = 10.394(3) Å, c = 10.837(3) Å, α = 111.774(5)°, β = 104.050(5)°, γ = 99.446(5)°, μ = 0.093 mm−1, V = 776.6(4) Å3, z = 2, Dx = 1.293 mg/m3, F(000) = 320, T = 293(2) K, 2.14° ≤ θ ≤ 25.03°, the final R factor: R1 = 0.0582, wR2 = 0.1399. The distance of N(4)

Ferulic acid and ferulic acid derivative anti-phytoviral agents

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