Abstract
In this article, we showed the synthesis of new polycyclic aromatic compounds, such as thienotriazolopyrimidinones, N-(thienotriazolopyrimidine) acetamide, 2-mercapto-thienotriazolo-pyrimidinones, 2-(((thieno-triazolopyrimidine) methyl) thio) thieno-triazolopyrimidines, thieno-pyrimidotriazolo-thiazines, pyrrolo-triazolo-thienopyrimidines, thienopyrimido-triazolopyrrolo-quinoxalines, thienopyrimido-triazolo-pyrrolo-oxathiino-quinoxalinones, 1,4-oxathiino-pyrrolo- triazolothienopyrimidinones, imidazopyrrolotriazolothienopyrimidines and 1,2,4-triazoloimidazo- pyrrolotriazolothienopyrimidindiones, based on the starting material 2,3-diamino-6-benzoyl-5- methylthieno[2,3-d]pyrimidin-4(3H)-one (3). The chemical structures were confirmed using many spectroscopic ways (IR, 1H, 13C, −NMR and MS) and elemental analyses. A series of thiazine, imidazole, pyrrole, thienotriazolopyrimidine derivatives were synthesized and evaluated for their antiproliferative activity against four human cancer cell lines, i.e., CNE2 (nasopharyngeal), KB (oral), MCF-7 (breast) and MGC-803 (gastric) carcinoma cells. The compounds 20, 19, 17, 16 and 11 showed significant cytotoxicity against types of human cancer cell lines.
Highlights
Cancer is one of the most recent serious diseases that afflict humans and leads to their death
The chemical studies of each of thiophene, pyrimidine, triazole, thiazine, pyrrole, quinoxaline and imidazole nucleus play a significant role in the synthesis of a diversity of fused heterocyclic compounds having a wide range of biological and pharmacological activities
Through the final results of the effect of compounds against the types of human carcinoma cell lines, we found many compounds, such as 20–19, 17–16, 11 and 18 gave the highest anticancer activity
Summary
Cancer is one of the most recent serious diseases that afflict humans and leads to their death. Researchers began to develop and discover much effective anticancer therapeutics, such as treatment of cancer using chemotherapy [1] and heterocyclic compounds, such as thienopyrimidine, triazolopyrimidine, quinoxaline and imidazole derivatives containing anticancer drugs [2], as follows: Azathioprine, Pimonidazole, Dacarbazine, Misonidazole, Fadrozole, Tipifarnib, Bendamustine, Indimitecan and Nilotinib. The thiazolopyrimidine, 1,2,4-triazolopy- rimidine and thienotriazolopyrimidinone derivatives possess such biological activities as Molecules 2021,[2164, ]2,03a1nti-hyperlipidemia [15], antidepressant, anti-inflammatory and antimicrobial activ- 2 of 20 ities [16]. The thiazolopyrimidine, 1, 2, 4-triazolopy- rimidine and thienotriazolopyrimidinone derivatives possess such biological activities as anti-inflammatory and analgesic activityan[1ti7-i,n1fl8a],mamntaitmoriycraonbdiaaln[a1lg9e]saicnadctainvittiyca[1n7c,e1r8]a, catnivtiimtyictrhobroiaul g[1h9]aapnodtaennttiicaalnocfer activity the enzyme (PARthPr-o1u)gihnhaipboitieonntia[l2o0f].thLeateenlzyy,mine c(PoAnRnPec-1ti)oinnhtiobictioonnt[i2n0u]i.nLgatwelyo,rikn icnonthnecstiyonn-to continthesis and biologuicnaglweovrakluinatihoensyonfthneeswis apnodlybcioylcolgiiccafluesveadlutahtioennoopf nyerwimpidoliyncey,clpicufruinseedatnhidenopyrim1,2,4-triazole sysitdeimnes,,ppuurrinineeandder1i,v2a,4t-itvreiaszaorlee soyfstgermeas,t pimurpinoertdaenrciveaatinvdeswariedoefagprepalitciamtipoonrstance and in many biologicwaildaecatpivpiltiiceast,iosnuschin amsaannytibtiuomlogoirca[2l 1ac]taivnidtietsh, esupchotaesnatinatlituxamnotrh[i2n1e] oanxdidtahseepotential (XO)-inhibitory axcatnivthitiniees,oaxsidwaseell(aXsOm)-iannhyibbitioorlyogaicctaivl iaticetsi,vaitsiewsewllhaesnmfuanseydbwioliothgi1c,a2l,4a-cttriviait-ies when zole ring, shown1fu,i2sn,e4d-Ftriwgiauiztrhoel1o1,p2,u,4ar-istnrteiahsze(oAfleo) l[rl2ion2w]g,,i1ns,2hg,o4:w-7trβnia-iDzno-Flroiigbpuourfreuinr1ea,sna(osBst)yh[el2-31f]o,,2ltl,ho4iw-etnrinioagtzr:ioa7lzβoo-plDou-prryiinbroiemfsuidrainnoonsyels(A) [22], 1,2,4-tria(Czo) laonpdu2r-isnuebs-t(hBi)en[2o3t]r,iatzhoielonpoytrriimazidoilnoopnyersim(Did) iansoanneesw(Cc)laasnsdof2-thsuebX-Othiiennhoib-itors [24]. The thiazolopyrimidine, 1, 2, 4-triazolopy- rimidine and thienotriazolopyrimidinone derivatives possess such biological activities as anti-inflammatory and analgesic activityan[1ti7-i,n1fl8a],mamntaitmoriycraonbdiaaln[a1lg9e]saicnadctainvittiyca[1n7c,e1r8]a, catnivtiimtyictrhobroiaul g[1h9]aapnodtaennttiicaalnocfer activity the enzyme (PARthPr-o1u)gihnhaipboitieonntia[l2o0f].thLeateenlzyy,mine c(PoAnRnPec-1ti)oinnhtiobictioonnt[i2n0u]i.nLgatwelyo,rikn icnonthnecstiyonn-to continthesis and biologuicnaglweovrakluinatihoensyonfthneeswis apnodlybcioylcolgiiccafluesveadlutahtioennoopf nyerwimpidoliyncey,clpicufruinseedatnhidenopyrim1,2,4-triazole sysitdeimnes,,ppuurrinineeandder1i,v2a,4t-itvreiaszaorlee soyfstgermeas,t pimurpinoertdaenrciveaatinvdeswariedoefagprepalitciamtipoonrstance and in many biologicwaildaecatpivpiltiiceast,iosnuschin amsaannytibtiuomlogoirca[2l 1ac]taivnidtietsh, esupchotaesnatinatlituxamnotrh[i2n1e] oanxdidtahseepotential (XO)-inhibitory axcatnivthitiniees,oaxsidwaseell(aXsOm)-iannhyibbitioorlyogaicctaivl iaticetsi,vaitsiewsewllhaesnmfuanseydbwioliothgi1c,a2l,4a-cttriviait-ies when zole ring, shown1fu,i2sn,e4d-Ftriwgiauiztrhoel1o1,p2,u,4ar-istnrteiahsze(oAfleo) l[rl2ion2w]g,,i1ns,2hg,o4:w-7trβnia-iDzno-Flroiigbpuourfreuinr1ea,sna(osBst)yh[el2-31f]o,,2ltl,ho4iw-etnrinioagtzr:ioa7lzβoo-plDou-prryiinbroiemfsuidrainnoonsyels(A) [22], 1,2,4-tria(Czo) laonpdu2r-isnuebs-t(hBi)en[2o3t]r,iatzhoielonpoytrriimazidoilnoopnyersim(Did) iansoanneesw(Cc)laasnsdof2-thsuebX-Othiiennhoib-itors [24]. triazolopyrimidiAnodndeitsio(nDa)llay,sAaznatehwiocplrainsse o(Ef)tihseanXOanitnichanibcietrodrsru[g24th].aAt pdodsisteisosneaslcloyn, sAidzeartahbiloe-potential, prine (E) is an anbteiccanuscerodf irtus gabtihliatyt ptoosinsteesrsfesrecwonitshidDeNraAblpereppoatreendtiaanld, btehceanusstoepofgriotswatbhialintyd division to interfere with cDelNlsAanpdrietpisaruesdedafnodr tthheetnresattompegntroowf mthetaanstdatdicivmiasliiognnacnetllms ealnadnoimt iasaunsdedcefllocrarcinoma the treatment of omf ethtaesptaatniccremaas l[i2g5n].ant melanoma and cell carcinoma of the pancreas [25]
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