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In this study, new derivatives of pyrazolo[3,4\u2010<jats:italic>d<\/jats:italic>]pyrimidine were synthesized by alkylation of the N1 nitrogen atom. We synthesized 3\u2010iodo\u20101<jats:italic>H<\/jats:italic>\u2010pyrazolo[3,4\u2010<jats:italic>d<\/jats:italic>]pyrimidin\u20104\u2010amine <jats:bold>2<\/jats:bold> from commercially available aminopyrazolopyrimidine <jats:bold>1<\/jats:bold> using <jats:italic>N<\/jats:italic>\u2010iodosuccinimide as an iodinating agent. The synthesis of compound <jats:bold>2<\/jats:bold> started with nucleophilic substitution of 3\u2010iodo\u20101<jats:italic>H<\/jats:italic>\u2010pyrazolo[3,4\u2010<jats:italic>d<\/jats:italic>]pyrimidin\u20104\u2010amine with R\u2013X (X: \u2013OMs, \u2013Br, \u2013Cl), affording\u00a0<jats:italic>N<\/jats:italic>\u2010alkylated pyrazolo[3,4\u2010<jats:italic>d<\/jats:italic>]pyrimidine. We performed this synthesis using a weak inorganic base\u00a0and the mild temperature was also used for a two\u2010step procedure to generate <jats:italic>N<\/jats:italic>\u2010alkylated pyrazolo[3,4\u2010<jats:italic>d<\/jats:italic>]pyrimidine derivatives. Also, all compounds were tested for their ability to inhibit acetylcholinesterase (AChE) and the human carbonic anhydrase (hCA) isoforms I and II, with <jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub> values in the range of 15.41\u2009\u00b1\u20091.39\u201363.03\u2009\u00b1\u200910.68\u2009nM for AChE, 17.68\u2009\u00b1\u20091.92\u201366.27\u2009\u00b1\u20095.43\u2009nM for hCA I, and 8.41\u2009\u00b1\u20092.03\u201328.60\u2009\u00b1\u20097.32\u2009nM for hCA II. Notably, compound <jats:bold>10<\/jats:bold> was the most selective and potent CA I inhibitor with a significant selectivity ratio of 26.90.<\/jats:p>","DOI":"10.1002\/ardp.202000330","type":"journal-article","created":{"date-parts":[[2021,1,27]],"date-time":"2021-01-27T13:08:22Z","timestamp":1611752902000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Synthesis of <i>N<\/i>\u2010alkylated pyrazolo[3,4\u2010<i>d<\/i>]pyrimidine analogs and evaluation of acetylcholinesterase and carbonic anhydrase inhibition properties"],"prefix":"10.1002","volume":"354","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0045-5254","authenticated-orcid":false,"given":"Busra O.","family":"Aydin","sequence":"first","affiliation":[{"name":"Department of Chemistry, Faculty of Science Ataturk University  Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2584-275X","authenticated-orcid":false,"given":"Derya","family":"Anil","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Faculty of Science Ataturk University  Erzurum Turkey"},{"name":"Department of Chemistry and Chemical Process Technologies, Technical Sciences Vocational School Ataturk University  Erzurum Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3216-1098","authenticated-orcid":false,"given":"Yeliz","family":"Demir","sequence":"additional","affiliation":[{"name":"Department of Pharmacy Services, Nihat Delibalta G\u00f6le Vocational School Ardahan University  Ardahan Turkey"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,1,27]]},"reference":[{"key":"e_1_2_5_2_1","doi-asserted-by":"publisher","DOI":"10.11648\/j.sjc.20180605.12"},{"key":"e_1_2_5_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2009.09.040"},{"issue":"6","key":"e_1_2_5_4_1","first-page":"88","volume":"8","author":"Merugu R.","year":"2015","journal-title":"Int. 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