Synthesis Of Glycosylamino And Benzothiazole Deteratives Bearing Aryltetrazole

Tetrazoles have a wide range of pharmaceutical applications, where they act as stimulants or sedatives on the central nervous system. These compounds have antiinflammatory, antilipemic, antimicrobial, and antiallergic activities. Moreover, such compounds are useful as oxidizers and effective agents for regulating plant growth and as explosives and rocket propellants. Thus we have designed and synthesized two classes unreported compounds , which basic scaffold are aryltetrazole.Substituted 1,3,4-Oxadiazoles and 1,3,4-thiadiazoles are very important two classes of heterocyclic compounds with a wide range of pharmaceutical and biological activity. Many 1,3,4-Oxadiazoles have also shown antibacterial, antifungal, and muscle relaxant properties. The benzothiazole constitutes an important scaffold of drugs, which may possess several pharmacological functions, such as powerful antitumour agents, neurotransmission blocker, calmodulin (CaM) antagonists, neuroprotective agent and exhibit other interesting biological activities. Thus we have designed and synthesized 2-[(1-aryl-1H-tetrazol-5-yl)thiomethyl- ene]-5-glycosylamino-1,3,4-oxadiazole/1,3,4-thiadiazole and N-(4/6-substituted benzothiazol- 2-yl)-S-[(1-aryl-tetrazol-1H-5-yl)mercapto]acetamide.All the target compounds were characterized by IR, 1H NMR and elemental analysis.The major works of this thesis1. N-glycosyl-2-[S-(1-aryl-1H-tetrazol-5-yl)mercaptoacetamido]thioureas have been synthesized from S-(1-aryl-1H-tetrazol-5-yl)mercaptoacetohydrazine and glycosyl isothiocyanates, then were converted to a series of new 2-[(1-aryl-1H-tetrazol-5- yl)thiomethylene]-5-glycosylamino-1,34-oxadiazoles/thiadiazoles respectively under mercuric acetate/alcohol system and acetic anhydride/ phosphoric acid system. The activity screen were performed for them , the screening models wereα1B adrenergic receptor agonists flow of calcium screening model and Escherichia coli typeⅠmethionine aminopeptidase (EcMetAP1).2. The intermediates 1-aryl-1H-5-mercaptotetrazole were attained from aryl isothiocyanate and sodium azide in the aqueous phase, another intermediates N-(substituted benzothiazol-2-yl)chloroacetamide were yielded from substituted 2-aminobenzothiazole and chloroacetyl chloride. Then N-(4/6-substituted benzothiazol-2-yl)-S-[(1-aryl-tetrazol -1H-5-yl)mercapto]acetamide were synthesized from the two compounds above in the presence of sodium hydroxide. The activity screen were performed for them, the screening models were Protein tyrosine phosphataseα(PTPα) and Gastric cancer-related protein-tyrosine phosphorus 1(SAP-1).The Innovations of the Thesis:1 Unreported compounds 2-[(1-aryl-1H-tetrazol-5-yl)thiomethylene]-5-glycosylamino-1,3, 4-oxadiazole/thiadiazoles. Particularly, the conditions of crystallization and reaction were investigated.2 A series of new small heterocyclic compounds N-(4/6-substituted benzothiazol-2-yl)- S-[(1-aryl-tetrazol-1H-5-yl)mercapto]thioacetamide were synthesized by SN2 reactions of 1-aryl-1H-5-mercaptotetrazole and N-(substituted benzothiazol-2-yl)chloroacetamide.