Synthesis And Biological Activity Test Of Azole Derivatives Based On The N-bit Of Glucosamine

D-Glucosamine, a naturally occurring monosaccharide, mainly exist in the shrimp, crab and other shell animals, has a wide range of sources. It is not only the synthesis of glycolipids, glycoproteins, and polysaccharides, the precursor synthesis of collagen, but also can repair damaged cartilage, has a certain effect on osteoarthritis, has a variety of biological activity. Their derivatives also have more biological activities, have a more widely used in the medical field. Azole compounds are an important class of heterocyclic compounds, which have a wealth of electrons, easy to form hydrogen bonding, ligand with metal ions and π-π stacking, electrostatic and hydrophobic, and other non-covalent. This structure gives the azole compound many special biological properties, and the azole compounds play an important role in the fields of agriculture, medicine and other fields.It has become the hot point that glucosamine molecule was introduced in the specific structure unit to synthesis of novel small molecule compounds used in the study of biological activity. Related studies can not only rich the library, also can promote the design and synthesis of oligosaccharides and sugar peptide, it is of great significance in the field of life science and related fields. Therefore, It is hoped that a molecule is synthesized containing the D-glucosamine and azole compound in order to take the advantage of both of them and find novel bio-active compounds. In this paper, 31 glucosamine azole derivatives were synthesized, and the compound structures were confirmed by IR, 1H NMR and ESI-HRMS, and the compounds were tested on anti-acetylcholinesterase activity to filter high biological activity compounds. Thesis is divided into the following sections:The first part mainly introduced the progress in carbohydrate drugs and modification of glucosamine N-bit, and propose main purpose and significance of this thesis, make a summary of the difficulties and innovation research.The second part mainly synthesized 10 1,3,4-oxadiazole derivatives containing glucosamine molecule. The main intermediate of glycosyl isothiocyanate was synthesized via hydroxyl protection by benzyl with glucosamine hydrochloride as starting material. The target compounds were synthesized from glycosyl isothiocyanate and hydrazide under the action of toluene sulfonyl chloride and triethylamine. The reaction conditions were optimized in the experiment.The third part mainly synthesized 13 1,3,4-thiadiazole derivatives containing glucosamine molecule. The glycosyl thiosemicarbazide, the key intermediate, was synthesized from the glycosyl isothiocyanate and hydrazine hydrate. The target compounds were synthesized from glycosyl thiosemicarbazide and aldehyde under the action of ammonium ferric sulfate. The reaction conditions were optimized in the experiment.The forth part mainly synthesized 8 triazolothiadiazole derivatives containing glucosamine molecule from glycosyl isothiocyanate and 3-substituent-4-amino-5-sulfydryl-1,2,4-triazoles. The reaction conditions were optimized in the experiment.The fifth part mainly studied the acetylcholinesterase inhibitory activities of the 31 target compounds using Ellman method to filter high anti-acetylcholinesterase activity compounds.