Synthesis of 2-[{4-(t-amino-1-yl) but-2-yn-1-yl }oxy]-1,3-benzothiazole derivatives as H3-antagonists
Journal Title: IOSR Journal of Pharmacy (IOSRPHR) - Year 2014, Vol 4, Issue 9
Abstract
Aminoacetylenicoxybenzothiazole derivatives were synthesized from the reaction of 2- hydroxybenzothiazole with 3-bromoprop-1-yne to generate 2-(prop-2-ynl-1-yloxy)-1,3-benzothiazole (RM-1). A mixture of 2-(prop-2-yn-1-yloxy)-1,3-benzothiazole, paraformaldehyde, cyclic amine and cuprous chloride catalytic amount, in peroxide-free dioxane through Mannich reaction yielded the desired aminoacetylenicoxybenzothiazoles (RM- 2-7). The mp, IR, 1H-NMR, 13C-NMR and elemental analysis were consistent with the assigned structures. The design of these compounds as H3 antagonists was based on the rationalization for the important criteria needed to overlap effectively with H3 receptor to induce antagonistic activity. These criteria are: 1) The basic amino group for ionic binding. 2) The acetylenic group for electrostatic interaction. 3) The 2-butyne provide the appropriate distance between the basic nitrogen and benzthiazole. 4) Oxy ether to provide hydrogen bonding with H3 receptor and 5) benzothiazole group found in H3 antagonists and many other biologically active compounds. The docking results showed that all the designed compounds have a good H3 receptor antagonism especially RM-7 which have -6 (kcal/mol). These results provide a good lead to design more effective H3 antagonists in managing Alzheimer's and other diseases like depression, epilepsy, schizophrenia and many other CNS disorders.
Authors and Affiliations
Ragheed Al- Rahmani , Elham Al-kaissi , Tawfeeq Arafat , Mohammad Ghattas , Zuhair Muhi-eldeen
Keywords
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