54097-74-4

Usage

InChI:InChI=1/C11H19N3S/c1-9(2)5-4-6-10(3)7-8-13-14-11(12)15/h5,7-8H,4,6H2,1-3H3,(H3,12,14,15)/b10-7-,13-8+

Upstream product

• 79-19-6 thiosemicarbazide 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 141-27-5 3,7-dimethyl-2,6-octadienal 

Relevant academic research and scientific papers

Usnic Acid Conjugates with Monoterpenoids as Potent Tyrosyl-DNA Phosphodiesterase 1 Inhibitors

Hybrid molecules created from different pharmacophores of natural and synthetic equivalents are successfully used in pharmaceutical practice. One promising target for anticancer therapy is tyrosyl-DNA phosphodiesterase 1 (Tdp1) because it can repair DNA lesions caused by DNA-topoisomerase 1 (Top1) inhibitors, resulting in drug resistance. In this study, new hybrid compounds were synthesized by combining the pharmacophoric moiety of a set of natural compounds with inhibitory properties against Tdp1, particularly, phenolic usnic acid and a set of different monoterpenoid fragments. These fragments were connected through a hydrazinothiazole linker. The inhibitory properties of the new compounds mainly depended on the structure of the terpenoid moieties. The two most potent compounds, 9a and 9b, were synthesized from citral and citronellal, which contain acyclic fragments with IC50 values in the range of 10-16 nM. Some synthesized derivatives showed low cytotoxicity against HeLa cells and increased the effect of the Top1 inhibitor topotecan in vitro by three to seven times. These derivatives may be considered as potential agents for the development of anticancer therapies when combined with Top1 inhibitors.

Novel Citral-thiazolyl Hydrazine Derivatives as Promising Antifungal Agents against Phytopathogenic Fungi

To develop new antifungal agents against phytopathogenic fungi, a series of citral-thiazolyl hydrazine derivatives were designed, synthesized, and characterized by FT-IR, 1H NMR, 13C NMR, and HRMS. Antifungal activity results showed that most synthetic compounds exhibited broad-spectrum antifungal activities against six phytopathogenic fungi in vitro. Notably, compounds b and c15 exhibited remarkable antifungal activity against Colletotrichum gloeosprioides, Rhizoctonia solani, Phytophthora nicotianae var. nicotianae, Diplodia pinea, Colletotrichum acutatum, and Fusarium oxysporum f. sp. niveum, which were all superior to the positive control tricyclazole. Structure-activity relationship (SAR) studies demonstrated that introducing electron-withdrawing groups such as F on the benzene ring exhibited outstanding antifungal activities against all the tested fungi. Furthermore, compound b could effectively control rice sheath blight and showed higher curative activities against R. solani than validamycin·bacillus in vivo. In addition, the in vitro cytotoxicity results indicated that compound b possessed moderate cytotoxicity activity, and all citral-thiazolyl hydrazine derivatives exhibited lower or no cytotoxicity to the LO2 and HEK293 cell lines. In addition, the acute oral toxicity test showed that compound b had moderate toxicity (level II) with an LD50 value of 310 mg/kg ?bw (95% confidence limit: 175-550 mg/kg ?bw). Finally, a preliminary action mechanism study showed that causing obvious malformation of mycelium and increasing cell membrane permeability are two of the potential mechanisms by which compound b exerts antifungal activity. The present work indicates that some of these derivatives may serve as novel potential fungicides, and compound b is expected to be the leading structure for the development of new antifungal agents.

Citral thiazole hydrazone derivatives as well as preparation method and application thereof

The invention discloses citral thiazole hydrazone derivatives as well as a preparation method and application thereof. The preparation method comprises the following steps of: 1) dissolving thiosemicarbazide in water, heating to 40-80 DEG C to dissolve thiosemicarbazide, dissolving citral in an organic solvent, dropwise adding into a thiosemicarbazide aqueous solution, reacting at 40-80 DEG C, cooling to room temperature, separating out solids, filtering, and washing a filter cake with the organic solvent to obtain citral thiosemicarbazide, and 2) dissolving citral thiosemicarbazone and alpha-bromo-substituted acetophenone in an organic solvent, stirring at room temperature for 10-100 minutes, carrying out suction filtration on solid powder after the reaction is finished, and recrystallizing to obtain the citral thiazole hydrazone derivative. The derivative has good bacteriostatic activity on plant pathogenic fungi and can be widely applied to preparation of antibacterial agents.