<\/p>\n
2-Mercaptobenzoimidazoles are an interesting class of heterocycles in medicinal chemistry as their core structure is part of\u00a0different established therapeutics. The most prominent ones of\u00a0these drugs are omeprazole<\/a>,\u00a0which acts as a protonpump inhibitor to prevent the production of an excess of\u00a0gastric acid and fabomotizole (the former known as afobazole<\/a>),\u00a0an anxiolytic drug which interacts with ligand-dependent\u00a0human ion channels (GABA receptors<\/a>). Other 2-mercaptobenzoimidazoles, known for their antiviral activity,\u00a0have been\u00a0identified as potent ligands for estrogen and the CRTh2 receptors,\u00a0and have been shown to act as allosteric modulators of\u00a0the protein kinase PDK1.\u00a0Recently, novel N-substituted\u00a02-mercaptobenzo-imidazole derivatives have\u00a0been shown to be potent candidates in the search for novel drugs\u00a0against castration resistant prostate cancer. These new 2-mercaptobenzoimidazoles interact with the binding function 3 (BF3)\u00a0pocket of the androgen receptor which results in a conformational change of a neighboured binding pocket and prevents its\u00a0interaction with a steroid activator protein.<\/p>\n The synthesis of 2-mercaptobenzoimidazoles and derivatives\u00a0thereof can be achieved via literature known procedures such as\u00a0the reaction of 1,2-diaminobenzenes with carbon disulfide and\u00a0subsequent alkylation with electrophiles or via direct alkylation\u00a0of the sodium thiolate of 2-mercaptobenzoimidazole with\u00a0chloroalkyl anilides.\u00a0Besides manifold strategies in solution\u00a0only few other procedures are reported that allow the syntheses of\u00a0different 2-mercaptobenzoimidazoles on solid supports. An\u00a0example for such a resin-based procedure is the synthesis of the\u00a02-mercaptobenzoimidazole core on 4-methyl-benzhydrylamineresin (MBHA-resin) and reaction to biheterocyclic dihydroimidazole analogs, 2-alkylthio-imidazocoumarines, and\u00a01-alkyl-2-alkylthio-5-carba-moyl-benzoimidazoles.\u00a0Another\u00a0application using poly-ethylene-glycol-resins as soluble polymers\u00a0has been reported for the synthesis of different bisbenzoimidazoles via ring closure through intramolecular nucleophilic attack of an immobilized amino group on an amide\u00a0carbonyl functionality.18 In this study, we aimed for the development of a novel solid supported protocol for the synthesis of\u00a0N-substituted 2-mercaptobenzoimidazoles allowing a novel\u00a0access to diverse derivatives of this attractive compound class.<\/p>\n The herein described procedure presents as far as we know the\u00a0first strategy for the synthesis of S,N-alkylated 2-mercptobenzoimidazoles on solid phases enabling a combinatorial approach to\u00a0N-alkylated 2-mercaptobenzoimidazole libraries. The modularity\u00a0of this method has been demonstrated by a synthetic procedure\u00a0consisting of two different linkers, on which the 2-mercaptobenzoimidazole was generated and modified on bead by Mitsunobu etherification. The resulting immobilized S,N-alkylated\u00a0heterocycles have been cleaved in a multifunctional strategy\u00a0either via transesterification or aminolysis. The herein developed\u00a0methodology enables the extension of the protocol to increase\u00a0the diversity of the synthesized N-substituted 2-mercaptobenzoimidazoles via exchange of the building blocks I\u2013IV, e.g.\u00a0through etherification with thiophenols or the attachment of\u00a0other alkyl linker units in future applications.<\/p>\n <\/p>\n Susanto, Steven, Nicole Jung, and Stefan Br\u00e4se. “Solid phase syntheses of S, N-substituted 2-mercaptobenzoimidazoles.”\u00a0RSC Advances<\/i><\/em>\u00a06.46 (2016): 39573-39576.<\/p>\n <\/p>\n 2-Mercaptobenzoimidazoles are an interesting class of heterocycles in medicinal chemistry as their core structure is part of\u00a0different established therapeutics. The most prominent ones of\u00a0these drugs are omeprazole,\u00a0which acts as […]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":[],"categories":[7,181],"tags":[422],"_links":{"self":[{"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/posts\/634"}],"collection":[{"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/comments?post=634"}],"version-history":[{"count":2,"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/posts\/634\/revisions"}],"predecessor-version":[{"id":636,"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/posts\/634\/revisions\/636"}],"wp:attachment":[{"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/media?parent=634"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/categories?post=634"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.bocsci.com\/blog\/wp-json\/wp\/v2\/tags?post=634"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}Reference:<\/h4>\n
Related Products:<\/h4>\n
<\/th> <\/th> <\/th> <\/th> <\/th><\/tr><\/thead> CAS Number <\/td> Product Name <\/td> Molecular Weight <\/td> Molecular Formula <\/td> Description <\/td><\/tr> 73590-58-6 <\/td> Omeprazole<\/a><\/td> 345.42 <\/td> C17H19N3O3S <\/td> Omeprazole is a proton pump inhibitor used in the treatment of dyspepsia. <\/td><\/tr> 173352-21-1 <\/td> Afobazole<\/a><\/td> 307.41 <\/td> C15H21N3O2S <\/td> Fabomotizole (brand name Afobazole) is an anxiolytic drug launched in Russia in the early 2000s. It produces anxiolytic and neuroprotective effects without any sedative or muscle relaxant actions. <\/td><\/tr><\/tbody><\/table><\/div>\n","protected":false},"excerpt":{"rendered":"