Zining Cui

New class of potent antitumor acylhydrazone derivatives containing furan.

A pair of chemical isomeric structures of N-acylhydrazone compounds I and II were designed and synthesized. The reaction was carried out with high diastereoselectivity to obtain one configurational isomer in excellent yields. The exact configuration and conformation of IIa and IIe were confirmed by the X-ray single crystal diffraction. The antitumor bioassay revealed that some compounds exhibited excellent activity against the selected cancer cell lines. In particular, IIf (IC50=16.4 μM) was better than doxorubicin (IC50=53.3 μM) against human promyelocytic leukemic cells (HL-60). Their toxicities were predicted in silico. The results showed that compounds II were safe and eligible to be development candidates. IIf showed great promise as a novel lead compound for further anticancer discovery.

Molecular design, synthesis and bioactivity of glycosyl hydrazine and hydrazone derivatives: notable effects of the sugar moiety.

Assuming that the water solubility of our previous hydrazone derivatives would improve after modification with sugars while keeping or modulating their notable biological activities, we designed and synthesized some glycosyl hydrazine and hydrazone derivatives. Bioassay results indicated that the antitumor activity of our previously prepared hydrazones reduced or disappeared after modification with sugars. On the contrary, some glycosyl derivatives displayed much better antifungal activity against selected fungi. Obviously, a small sugar can change the biological activity of hydrazones significantly.

Synthesis and bioactivity of N-benzoyl-N′-[5-(2′-substituted phenyl)-2-furoyl] semicarbazide derivatives.

In order to find novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates with 5-(substituted phenyl)-2-furoyl hydrazine, and the structures were confirmed by IR, 1H-NMR, elemental analysis and single crystal X-ray diffraction analyses (compound E2). The bioassay results indicated that the title compounds exhibit good insecticidal activity, especially towards Plutella xylostella L., but had lower fungicidal activity. Inspiringly, the title compounds possessed obvious anticancer activity against human promyelocytic leukemic cell line (HL-60), and some of the title compounds also had activity against human hepatocellular carcinoma cell line (Bel-7402), human gastric carcinoma cell line (BGC-823), and human nasopharyngeal carcinoma cell line (KB). The results indicated that the linkage in the lead compounds was important to the bioactivity and spectra. The modification on the urea linkage is an effective strategy to discover new pesticide and drug candidates.

Synthesis and bioactivities of novel pyrazole and triazole derivatives containing 5-phenyl-2-furan.

A series of novel pyrazole and triazole derivatives containing 5‐phenyl‐2‐furan functionality were designed and synthesized. Their toxicities were predicted using in silico assays and proven to be less toxic. The antitumor results showed that the activity of compounds containing 1,3,4‐triazole (series II) was higher than that of pyrazole‐attached derivatives (series I). Among them, IIa and IIg showed much higher activity against Bel‐7402 than doxorubicin. The fungicidal tests showed that most title compounds II exhibited great selectivity against Phytophthora capsici in vivo.

5-(4-Fluoro­phen­yl)-2-furylmethyl N-(2,6-difluoro­benzo­yl)carbamate

The title compound, C19H12F3NO4, was synthesized by the reaction of 5-(4-fluorophenyl)-2-furanmethanol and 2,6-difluorobenzoylisocyanate. The seven atoms of the fluorophenyl group are disordered over two positions with site occupancy factors ca 0.6 and 0.4. The dihedral angle between the furan and fluorophenyl rings is 1.58°. In the crystal structure, the molecules are linked via intermolecular N—H⋯O hydrogen bonds to form chains.

N'-tert-Butyl-5-(4-chloro-phen-yl)furan-2-carbohydrazide.

In the title molecule, C15H17ClN2O2, the furan and benzene rings form a dihedral angle of 15.35 (8)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains extended in the [010] direction.