New Series Of Piperidine Alcohol Synthesis And Multi-molybdate Oxide Synthetic Azo-benzothiazole Response Study

In order to find some lead compounds with activities of anti-cancer, and search the introduction compounds for new pesticide, obeying the 21st century principle of active-factor-addition, eighteen unreported compounds Ia～Ir have been designed and synthesized with substituted amines as raw materials via a series of Michael addition, Dieckmann condensation, hydrolysis decarboxylation and reactions with Grignard reagent. Complete assignments have been achieved for the title compounds by 1H NMR, IR, MS and elemental analysis. Meanwhile, their physic-chemical properties, spectrum properties, reaction conditions and synthetic methods were analyzed and discussed as well. In order to investigate the relationship between the structure and property of the title compounds, the single crystals of compounds Im, In, Io were cultured and confirmed by X-ray diffraction analyses. The characters of the crystal stuctures were briefly analyzed in the paper. The structural formulas of compounds Ia～Ir are as follows respectively: Ia: R=4-Me; n=1; Ar=Ph Ib: R=H; n =1; m=6, cyclohexyl Ic: R=4-MeO; n=1; Ar=PhId: R=4-Me; n=1; Ar=4-MeC6H4 Ie: R=4-Me; n=1; Ar=4-MeOC6H4 If: R=4-MeO; n=1; Ar=3-F-C6H4Ig: R=4-Me; n=1; m=6, cyclohexyl Ih: R=4-MeO; n=1; Ar=4-MeC6H4 Ii: R=4-MeO; n=1; Ar=4-MeOC6H4Ij: R=4-Me; n=1; m=5, cyclopentyl Ik: R=4-MeO; n=1; m=6, cyclohexyl Il: R=4-MeO; n=1; m=5, cyclopentylIm: R=4-Me; n=1; Ar=3-F-C6H4 In: R=H; n=2; Ar=PhIo: R=H; n=2; Ar=3-F-C6H4Ip: R=H; n=2; Ar=4-MeC6H4 Iq: R=H; n=2; Ar=4-MeOC6H4 Ir: R=H; n=2; m=6, cyclohexylAt the basis of the synthesis of organoimido derivatives of hexamolybdate, a new method to synthesize azo compounds have been found, in order to study the doubly dehydrogenative coupling (DDHC) reaction, three 2,2′-azobenzothiazole derivatives have been designed and synthesized with 2-aminobenzothiazole derivatives as raw materials via the doubly dehydrogenative coupling (DDHC) reaction by oxidation of (n-Bu4N)4[α-Mo8O26]. All of the title compounds were confirmed by UV/Vis, 1H NMR, IR, MS and elementary analysis. Their physic-chemical properties, spectrum properties, reaction conditions, plausible reaction mechanisms were briefly analyzed and discussed. In order to study the space structure, the single crystals of compounds IIa, IIb were cultured and confirmed by X-ray diffraction analyses. Two unreported crystal stuctures and the characters of the title compounds (IIa, IIb) were briefly analyzed and discussed in this paper. The structural formulas of compounds IIa～IIc and the reactions of synthesized azo compounds are shown as follows respectively:The growth inhibition activities of the title compounds against K562 were determined by the MTT assay according to the standard bioactivity test procedures of the Zooblast-molecular Biology Laboratory of Shanghai Normal University of China. The preliminary results show that the compounds have good inhibitory activities against K562 cells, the growth inhibition percentage is 70.16～87.46%, which is much higher than that of the anti-tumor drug of clinical practice 5-fluorouracil at the same concentration of 100 mg/L and have potential anti-leukemia bioactivities. Because the piperidine derivatives have pesticide activities, the bioactivities tests of the first series of compounds Ia～Ir were finished by the bioactivities test central of Huazhong Normal University of China. The results indicated that some compounds display good herbicidal activities to the root of some tested plants, such as the growth inhibition percentage of compound Im are 91.9 and 97.9% to the root of dicotyledon plant (Brassica campestris L.), monocotyledon plant (Echinochloa crusgallis L.), respectively; some compounds display selected bactericidal activities, but not good, such as the highest growth inhibition percentage of the compounds is only 76.19% (Im) to Dothiorella gregaria at 100 mg/L.