INTRODUCTION:

Cancerisoneamongstthe foremost serious clinicalissues,notablyindevelopedcountries,despiteadvancesinmedicineanalysisandtechnology.ConsistentwiththeWorldHealthOrganization(WHO),theincidenceofthisillnessisconcerninghalfdozenmillioncaseseachyear[1–3].

Thechemistryofpyrazolesystemhasattractedalotofattentionandlotsofstrategiesforsynthesisareextended[4].Pyrazole sexist in severalcompoundsthatareaunitusedasprescriptiondrugsand agrochemicals [5].Consolidatedpyrazoleshavefungicidal [6],herbicidal[7],veridical[8]andinsecticidalactivity.

Accordingly,wewantto style new compoundshavingmalignant tumor and antimicrobial activity atan equivalent time.Quinoxalinederivativesshowabroadspectrumofbiologicalactivitiestogetherwithantimicrobial[9–11],antiviral[12], anti-inflammatory,[13,14], anticancer activity[15,16].

EXPERIMENTAL SECTION:

Thin layer chromatography wasrunon silica gel-GandvisualizationwasdoneusingUVlightoriodine.IRspectrawererecordedbyPerkin-Elmer1000instrumentinKBrpellets.¹H–NMRspectrawererecordedinCDCl₃orDMSO-D₆solventusingtrimethylsilaneasinternalstandardby400MHzspectrometer.ByJeol-JMSD-300spectrometer,massspectrawererecorded.Startingmaterials,whichwereusedinthischapterwereobtainedbycommercialsourcesandusedassuch.

RESULTS AND DISCUSSIONS:

Quinoxaline7-amine(1)reactswithacetylchloridetoformN-(quinoxalin-7-yl)acetamide(2)whichoncondensationwithdifferentaromaticaldehydesgave3-(4-chlorophenyl)-N-(quinoxalin-7-yl) acrylamide(3a-g)Compound3oncylisationhydrazinehydrateofferedtitlecompounds.Allthesecompoundswerecharacterizedbyspectralanalysis.

R= Phenyl, 4-Chlorophenyl, 3-Chlorophenyl, 4-Fluoropheny, l,3-Fluorophenyl, 4-Methoxypheny, l,3-Methoxyphenyl

N-(quinoxalin-7-yl)acetamide

TothesolutionofQuinoxaline7-amine(1)(1eq.)inDCM(10mL/1g)wereaddedEt₃N(3eq.)andactylchloride(1.2eq.)at0°CandstirredatRTfor15h.Aftercompletionofreaction(checkedbyTLC),reactionmixturewasdilutedwithwater,extractedwithDCM.Organiclayerwaswashedwithwater,brine,dried(Na₂SO₄)andconcentrated.Crudematerialwaspurifiedby Silica gel (100-200mesh)columnchromatographyusing0-50%EAinhexane.

¹HNMR(DMSO-d₆,400MHz);=8.28(d,1H),7.71(d,1H),7.60(S,1H),7.51(m,2H),2.12(s,3H);MS:m/z,188(M⁺+H).

3-aryl-N-(quinoxalin-7-yl)acrylamide(3a-g)

TothesolutionofN-(quinoxalin-7-yl)acetamide(2)(1eq.)inMeOH(20mL/1g)wereaddedR-CHO(1eq.),and2%NaOH(5mL/1g)atRTandstirredatRTfor12h.Aftercompletionofreaction(checkedbyTLC),solventwasevaporatedunderreducedpressure,crudeproductwaspouredinice-water.Obtainedsolidwasfilteredandrecrystallizedfrommethanol.

N-(quinoxalin-7-yl)cinnamamide

¹HNMR(DMSO-d₆,400MHz);=8.27(d,2H),7.98(d,1H),7.75(d,1H),7.61(S,1H),7.49(m,2H),7.33(m,1H),7.21(d,2H),7.11(d,2H),6.95(m,1H);MS:m/z,276(M⁺+H).

3-(4-chlorophenyl)-N-(quinoxalin-7-yl) acrylamide

¹HNMR(DMSO-d₆,400MHz);8.25(d,2H),7.99(d,1H),7.75(d,1H),7.62(s,1H),7.49(m,2H),7.21(d,2H),7.11(d,2H),6.95(m,1H);MS:m/z,310(M⁺+H).

3-(3-chlorophenyl)-N-(quinoxalin-7-yl)acrylamide

¹HNMR(DMSO-d₆,400MHz);8.26(d,2H),7.97(d,1H),7.73(d,1H),7.61(s,1H),7.50(m,2H),7.21(d,2H),7.11(d,2H),6.96(m,1H);MS:m/z,310(M⁺+H).

3-(4-fluorophenyl)-N-(quinoxalin-7-yl)acrylamide

¹HNMR(DMSO-d₆,400MHz);8.25(m,2H),7.97(d,1H),7.77(d,1H),7.60(s,1H),7.49(m,2H),7.21(d,2H),7.13(m,2H),6.96(m,1H);MS:m/z,294(M⁺+H).

3-(3-fluorophenyl)-N-(quinoxalin-7-yl)acrylamide

¹HNMR(DMSO-d₆,400MHz);8.26(m,2H),7.96(d,1H),7.76(d,1H),7.59(s,1H),7.50(m,2H),7.21(d,2H),7.11(m,2H),6.96(m,1H);MS:m/z,294(M⁺+H).

3-(4-methoxyphenyl)-N-(quinoxalin-7-yl) acrylamide

¹HNMR(DMSO-d₆,400MHz);8.25(d,2H),7.98(d,1H),7.78(d,1H),7.61(s,1H),7.49(m,2H),7.21(d,2H),7.10(d,2H),6.95(m,1H),3.84(s,3H);MS:m/z,306(M⁺+H).

3-(3-methoxyphenyl)-N-(quinoxalin-7-yl) acrylamide

¹HNMR(DMSO-d₆,400MHz);8.26(d,2H),7.99(d,1H),7.79(d,1H),7.60(s,1H),7.50(m,2H),7.22(d,2H),7.12(d,2H),6.96(m,1H),3.83(s,3H);MS:m/z,306(M⁺+H).

1-(4,5-dihydro-5-aryl-3-(quinoxalin-7-ylamino) pyrazol-1-yl) ethanone(4a-g)

Tothesolutionof3-aryl-N-(quinoxalin-7-yl) acrylamide(3)(1eq.)inEtOH(20mL/1g)wereaddedhydrazinehydrate(2eq.),andfewdropsofglacial acetic acid andatRTandrefluxedfor8h.Aftercompletionofreaction(checkedbyTLC),solventwasevaporatedunderreducedpressure,crudeproductwaspouredinice-water.Obtainedsolidwasfilteredandrecrystallizedfrommethanol.

1-(4,5-dihydro-5-phenyl-3-(quinoxalin-7-ylamino) pyrazol-1-yl) ethenone

¹HNMR(DMSO-d₆,400MHz);=8.31(d,1H),7.78(m,1H),7.61(S,1H),7.51(m,2H),7.32(m,1H),7.21(d,2H),7.11(d,2H),5.08(m,1H),2.81(m,2H),2.01(S,3H);MS:m/z,332(M⁺+H).

1-(5-(4-chlorophenyl)-4,5-dihydro-3-(quinoxalin-7-ylamino) pyrazol-1-yl) ethenone

¹HNMR(DMSO-d₆,400MHz);=8.30(d,1H),7.77(m,1H),7.60(S,1H),7.50(m,2H),7.28(d,1H),7.11(d,2H),5.10(m,1H),2.82(m,2H),2.01(S,3H);MS:m/z,366(M⁺+H).

1-(5-(3-chlorophenyl)-4,5-dihydro-3-(quinoxalin-7-ylamino) pyrazol-1-yl) ethenone

¹HNMR(DMSO-d₆,400MHz);=8.28(d,1H),7.78(m,1H),7.61(S,1H),7.52(m,2H),7.29(d,2H),7.12(d,2H),5.09(m,1H),2.82(m,2H),2.02(S,3H);MS:m/z,366(M⁺+H).

1-(5-(4-fluorophenyl)-4,5-dihydro-3-(quinoxalin-7-ylamino) pyrazol-1-yl) ethenone

¹HNMR(DMSO-d₆,400MHz);=8.27(d,1H),7.79(m,1H),7.60(S,1H),7.52(m,2H),7.28(d,2H),7.11(m,2H),5.09(m,1H),2.80(m,2H),2.03(S,3H);MS:m/z,350(M⁺+H).

1-(5-(3-fluorophenyl)-4,5-dihydro-3-(quinoxalin-7-ylamino) pyrazol-1-yl)ethenone

¹HNMR(DMSO-d₆,400MHz);=8.26(d,1H),7.78(m,1H),7.61(m,1H),7.51(m,2H),7.27(d,2H),7.10(m,2H),5.10(m,1H),2.81(m,2H),2.02(S,3H);MS:m/z,350(M⁺+H).

1-(4,5-dihydro-5-(3-methoxyphenyl)-3-(quinoxalin-7-ylamino) pyrazol-1-yl) ethenone

¹HNMR(DMSO-d₆,400MHz);=8.21(d,1H),7.68(m,1H),7.60(S,1H),7.53(m,2H),7.28(d,2H),7.11(m,2H),5.09(m,1H),3.76(S,3H),2.80(m,2H),2.01(S,3H);MS:m/z,362(M⁺+H).

1-(4,5-dihydro-5-(2-methoxyphenyl)-3-(quinoxalin-7-ylamino) pyrazol-1-yl) ethenone

¹HNMR(DMSO-d₆,400MHz);=8.22(d,1H),7.69(m,1H),7.61(S,1H),7.52(m,2H),7.29(d,2H),7.10(m,2H),5.09(m,1H),3.77(S,3H),2.81(m,2H),2.02(S,3H);MS:m/z,362(M⁺+H).

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Received on 21.06.2017 Modified on 10.07.2017

Asian J. Research Chem. 2017; 10(4):454-458.

DOI:10.5958/0974-4150.2017.00074.8