Study On The Synthesis And Characters Of Aromatic Bridged Bissaccharide Pseudoamides

Glycose chemistry as an old but new subject, plays an important effect in many places. Glycosyl group was an important function group in decoration of leading molecular. Introduce of glycosyl group can change the distribution coefficient of drug and make it easy to penetrate biological membrane, accelerate absorption efficiency of drugs, improve biological availability and decrease toxic and side effect of drugs. Thiourea compounds with antibacterial, anticancer, anti-inflammatory, anti-virus, blood diseases, pesticides and other biological activity, while have a certain pharmacological activity on leprosy, rheumatism, malaria, smallpox, tuberculosis, and some tumors; Because of strongly basic character, guanidine is an effective reagent which can be convenient and efficient to generate ion negative, it has great application in organic synthesis. Most of the compounds with single or multiple guanidine functional groups isolated from natural products have a wide range of antiviral and antitumor biological activities or pharmacological uses such as therapy for the hypertension and treatment of diabetes. These guanidine-containing molecules are found to be a critical part of many biological processes and promote the design and synthesis of new drugs. So, effectively synthesis guanidine and thiourea compounds in mild condition are one of interesting subjects for chemists.In this work, The O-protected anomeric carbon glycosyl isothiocyanate and non-anomeric isothiocyano glycose were refluxed with 1,3-diaminobenzene in CHCl3 to give 1,3-bis(N-glycosyl) thioureylenebenzene. Deacetylated in the solution of CH₃ONa/CH₃OH. Then, in the system of HgO/CH₃CN and catalysed by 4A molecular sieves, three 1,3-bis(N-glycosyl)thioureylenebenzene were reaceted with 2-amino-4/6-substituted-arylthiazoles to get 1,3-bis[N-(4/6-substituted-arylthiazole-2-yl) -N′-glycosyl-guanidino]benzenes. Two representative compounds were choosed to response to HSO₄^-, AcO^-, F^-, Cl^-, Br^-, I^-, binding abilities between receptorsand anions were investigated by 1H NMR. The PTP1B inhibit activity of the new compounds have been tested. The products were characterized by 1H NMR, IR spectral data and elemental analyses. The major accomplishments of this treatise:1. Anomeric carbon glycosyl isothiocyanate and non-anomeric isothiocyano glycose were prepared.2. The O-protected anomeric carbon glycosyl isothiocyanate and non-anomeric isothiocyano glycose were refluxed with 1,3-diaminobenzene in CHCl3 to give 1,3-bis(N-glycosyl) thioureylenebenzene. Then deacetylated in the solution of CH₃ONa/CH₃OH.3. In the system of HgO/CH₃CN and catalysed by 4A molecular sieves, three 1,3-bis(N-glycosyl)thioureylenebenzene were reaceted with 2-amino-4/6-substituted-arylthiazoles to get 1,3-bis[N-(4/6-substituted-arylthiazole-2-yl)-N′-glycosylguanidino]benzenes.4. Two representative compounds were choosed to interact to HSO₄^-, AcO^-, F^-, Cl^-, Br^-, I^-, binding abilities between receptorsand anions were investigated by 1H NMR.5. The PTP1B inhibit activity of the new compounds have been tested. These results revealed that the most compounds had high inhibit activity.