Abstract

Amongst sulfur- and nitrogen-containing heterocyclic compounds, the 2-aminothiazole scaffold is one of the characteristic structures in drug development as this essential revelation has several biological activities abiding it to act as an anticancer, antioxidant, antimicrobial and anti-inflammatory agent, among other things. Additionally, various 2-aminothiazole-based derivatives as medical drugs have been broadly used to remedy different kinds of diseases with high therapeutic influence, which has led to their wide innovations. Owing to their wide scale of biological activities, their structural variations have produced attention amongst medicinal chemists. The present review highlights the recently synthesized 2-aminothiazole-containing compounds in the last thirteen years (2008–2020). The originality of this proposal is based on the synthetic strategies developed to access the novel 2-aminothiazole derivatives (N-substituted, 3-substituted, 4-substituted, multi-substituted, aryl/alkyl substituents or acyl/other substituents). The literature reports many synthetic pathways of these 2-aminothiazoles associated with four different biological activities (anticancer, antioxidant, antimicrobial and anti-inflammatory activities). It is wished that this review will be accommodating for new views in the expedition for rationalistic designs of 2-aminothiazole-based medical synthetic pathways.

Highlights

  • Heterocyclic compounds are so important due to their versatile applications

  • A large number of heterocyclic compounds containing nitrogen and sulfur are used as medicine in different therapeutic targets

  • Thiazole and imidazole scaffolds are an essential kind of heterocyclic compound

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Summary

Introduction

Heterocyclic compounds are so important due to their versatile applications. A large number of heterocyclic compounds containing nitrogen and sulfur are used as medicine in different therapeutic targets. The thiazole derivative 10 was produced by heating phenacyl bromide with thiourea in ethyl alcohol, which acetylated by acetic anhydride to furnish the corresponding N-acetyl compound 11. ETffheectssyonnthheusimzeadn sKer5i6e3s of 2-laemukienmo-itahciealzlsol[e3-25]-.carboxylic acid phenylamide derivatives showed good anti-prolAifcecroartdivinegetfofetchtes soingnhifiucmanacneKof5t6h3elceaurkbeomxainailciedlelssi[d3e2]c.hain on the fifth position of the thiazole ring and the cytostatic impact on human chronic myeloid leukemia cell line K562, 2-aminothiazole-5-carbamides 28 were synthesized as outlined in Scheme 6. The compound 37b was acylated with Molecules 2021, 26, x FOR PEER REVIEWchloroacetyl chloride to give the corresponding chloroacetamide compound (Scheme 99)o.f All of these synthesized derivatives showed respectable anticancer activities toward HepG2 and PC12 cell lines. Heterocyclization of 2-aminothiazole 8 with α-bromo-3-methoxyacetophenone proceeded by heating in ethyl alcohol to yield 6-(3-methoxyphenyl)imidazo[2,1-b]thiazole 53, which underwent heating with 4-iodo-2-(methylthio)pyrimidine in the presence of palladium acetate, cesium carbonate and triphenyl phosphine to give the corresponding methyl thiopyrimidinyl compound 54 (Scheme 13). ScShcehmemee2255. .SSySyncnthhtheemssiiseso2of5f d.dSeeryriinvvtaahttiievvseeis99o11f.. derivative 91. sev2stt5rhili-i-sev2zoezav(eil-iec4ezpmeoavidtdre-cmhoraAfiAdttoinro2cAfio2lopnoi-eor2r-xrcaporthae-re-timy5rhaec-mahiate5llm-ahiicceiipt(al-ictcneityi4(ngiihtcrii4no-vivroreae-avt-orieani-nton5citet-a5octyte-ya5xdyyegs-x(tg-i(4ltsyie(csaw4asyec-4ttniltn-zaniultu-puaatptyacottydsshdcdishec)oeyaeeyytc-aewwxyttnntonnyhoyiooladnyadydpllifffsspdplalahaaaabbbzhhunccennzzooooeoeocntoottttnlttnininhya)h)eheooy-y-ddcldtxtxtalttl(huthuhai.haii9zhdidvcziecTz2aoeeataoitaoz)e)htzaen)an-aoyd)reo-dtwtr-rttlyh.ytlybe.hayehlaaiTclaiawTlcsias(thszas(sth9iuzeee9viuozru2oebvrdye2iolb)beylsteia)eylsttoswebwcyictwtntwbticioieutaeobcotaerumlauesdolmasieroensveemseprgnptbwedneeoriptrbiodataceouioinuocaaftaalonnouhtodnluncnelldnngtdoydlnddveaiicgvadlcdmeataiaanieawivvrcnmormliadieaawlnidonnyftrllioiiuhuulnidnteyfitensasotguhonvvsctisrenzeaattgaocgvisvsdyclcrarourcuatiatmofonaiosipialfronuvcufuoutieefnaoeopealpsosvnddffut.lefizceodsaotasoTnyaidrfcsfnvlhozmrntdaaiiabyevioavcvasenominvtneninsaditnveo.vdovereilcyidTovfwevisaafitslihe.enerarfylcedTforr2blnneavee-soihsndrtanarafiyynheeefvbmngtneninyweoonndeert-tltinhenlenhfeoniywetoecnsr-tl--r(Seracehgageenmentests(2S(6Sc)ch[he5em3m]e.eA2266c))o[[n55v33e]]..nAAienccotonnavcveeetnnyiieleannttitoaancceerteytyalalcattiitooionnnroerfae9cat2ciotbinoynosfoo9lfv29eb2nytb-sfyroelsveoelanvctee-nftryte-lfearteaieocenatycwe- tityhlaacltaeitotiioncnwawnithihtyhdaacrceiedttieiccaaafnnfohhryydderdidtehaefffNoor-rdadceeeddtytthlhaeeteNNd-a-pacceroetytdylaultacettde9dp3r.porTdouhdceutce9tl3e9.c3Tt.rhoTephheelieleiclctercaottprthoaicplkihciolaiftc-tahtetbatecankczkooofyftlhtcheaebtibeoennnzztoooyywllcacaratdtiison92toywiealrrdddessd992t2hyyeiiebeldledneedzdothythel eabmbeneinznozoyodlyaelmraimvinaiotnidoveedri9ev4rai.vtiAavteifv9ue4r.t9hA4e. rfAurreftuahcerttrihoenr roerfaetcahtcietoihonnigoohffltyhtheaechhtiiigvghahtllyeydaaccthilvoartoeadccechhtylloolrrcoohaalcoceertiytdylelcchrheloalorgirdeindeterweraeigathegne9tn2wtuwitnhidt9he2r9bu2anusdinecdrceboransbdiacistciioocnncdsoinw- daistpitoeirnofnsosrwmwaeasdsppteoerrfpfoorrrommdeueddcettoothperocdhulocreeotathhceeetccyhhllloaormrooaiancceoetydtylelarmaivmianitonivodeed9re5ivri[av5t3aivt]i.ev9e59[553[]5.3]

NNN N
SS OO NN
Dimroth rearrangment
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