Research Article Green Synthesis and In Vitro Biological ...downloads.hindawi.com › journals › jchem › 2013 › 542973.pdf · asitic [ ], antiparkinsonian [ , ], anticonvulsant

Hindawi Publishing CorporationJournal of ChemistryVolume 2013 Article ID 542973 4 pageshttpdxdoiorg1011552013542973

Research ArticleGreen Synthesis and In Vitro Biological Evaluation ofHeteroaryl Chalcones and Pyrazolines of Medicinal Interest

Vishal Banewar

Department of Chemistry Government Vidarbha Institute of Science amp Humanities Amravati 444 604 India

Correspondence should be addressed to Vishal Banewar banewargmailcom

Received 28 May 2013 Revised 11 September 2013 Accepted 19 September 2013

Academic Editor Naoki Haraguchi

Copyright copy 2013 Vishal Banewar This is an open access article distributed under the Creative Commons Attribution Licensewhich permits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

Pyrazolines are well known and important nitrogen containing 5-membered heterocyclic compounds In the present investigationa series of various heteroaryl chalcones and pyrazolines were synthesized by condensing formylquinolines with diverse ketonesThe newly synthesized 2-pyrazolines were characterized on the basis of elemental analysis and spectroscopic data All of the newlysynthesized target compounds were selected by the NCI for in vitro biological evaluationThese active compounds exhibited broadspectrum of various biological activities Most of the compounds showed potent activity

1 Introduction

Due to the rapid development of bacterial resistance toantibacterial agents it is vital to discover novel scaffold forthe design and synthesis of new antibacterial agents to helpin the battle against pathogenic microorganisms [1ndash3] Muchresearch has been carried out with the aim to discover thetherapeutic values of thiazole derivatives A large numberof substituted thiazole derivatives were prepared and testedfor variety of biological properties [4] such as antimicrobialactivity [5 6] Amongst the wide variety of heterocycles thathave been explored for developing pharmaceutically impor-tant molecules such as cyanopyridines [7ndash9] and triazolopy-ridines [10ndash12] have played an important role in medicinalchemistry They are reported to possess a broad spectrumof biological activity such as potential cardiovascular agentsantiviral [13] CNS depressant [14 15] bactericidal [16 17]and ulcer inhibitors [18 19] Furthermore researchers havealso revealed that Phenothiazine derivatives constitute animportant class of compounds possessing diverse type ofbiological properties including antiviral [20ndash22] antipar-asitic [23] antiparkinsonian [24 25] anticonvulsant [26]antihistaminic [27] and anthelmintic [28] properties

Encouraged by the literature reports and to assess thepharmacological profile of such class of compounds and incontinuation with the wok related to the synthesis spectral

studies and biological properties of pyrazolines herein wereport the synthesis of some novel pyrazolines and then theirantibacterial and antifungal activities in the present study

2 Materials and Methods

Melting points were determined by open capillary and areuncorrected The purity of the compounds was checkedusing precoated TLC plates (MERCK 60F) using chloro-form methanol water (1 4 5) solvent system The plateswere visualized under UV light (254 nm) IR spectra wererecorded using KBr on Shimadzu FTIR model 8000 spec-trophotometer and 1HNMRspectrawere recorded inDMSOon a BRUKER FT-NMR instrument using TMS as an internalstandard

3 Experimental Studies

31 General Methods for the Synthesis of Chalcones The threeprecursors 2-chloroquinoline-3-carbaldehyde 2-chloro-6-nitroquinoline-3-carbaldehyde and 6-bromo-2-chloroquin-oline-3-carbaldehyde were prepared by the reported methodin [29] Synthesis of the compounds (1andashd 2andashd and 3andashd) (Scheme 1) was based on Claisen-Schmidt condensation[30ndash32]

2 Journal of Chemistry

POCl3

NHCOCH3

a = b = c = d =

H3C H3C

DMF

NO2

R = H NO2 Br

Cl Cl

H

NN

O

OO

O

O

Ketone

R RR

(andashd)

1andashd 2andashd 3andashd

Scheme 1

Table 1 Physical properties of synthesized compounds

Compound ndashR (andashd) Molecular formula Yield Elemental analysisC H O N Cl Br

1a H a C15H12ClNO 83 6991 (6927) 469 (471) 621 (585) 543 (592) 1376 (1425)1b H b C16H14ClNO 75 7072 (7054) 519 (576) 589 (534) 515 (547) 1305 (1289)1c H c C18H11ClN2O3 71 6382 (6296) 327 (375) 1417 (1476) 827 (775) 1047 (1078)1d H d C18H12ClNO 62 7360 (7310) 412 (437) 545 (520) 477 (525) 1207 (1208)2a NO2 a C15H12N2O3 75 6716 (6725) 451 (425) 1789 (1775) 1044 (1075)2b NO2 b C16H14N2O3 80 6807 (6805) 500 (510) 1700 (1706) 992 (979)2c NO2 c C18H11N3O5 63 6189 (6178) 317 (308) 2290 (2276) 1203 (1238)2d NO2 d C18H12N2O3 64 7105 (7125) 397 (367) 1577 (1596) 921 (912)3a Br a C15H12BrNO 64 5962 (5961) 400 (410) 529 (531) 464 (461) 2644 (2637)3b Br b C16H14BrNO 60 6078 (6067) 446 (467) 506 (510) 443 (412) 2527 (2544)3c Br c C18H11BrN2O3 62 5642 (5612) 289 (287) 1253 (1223) 731 (745) 2085 (2133)3d Br d C18H12BrNO 82 6392 (6390) 358 (360) 473 (465) 414 (420) 2363 (2365)

Amixture of quinoline-3-carbaldehyde (001mol) ketoneandashd (010mol) and aq NaOH (4mL 10) in methanol(50mL) was refluxed for 2 h and the reaction mixture wasthen kept at 0∘C (24 h) Subsequently it was poured onto icecold water (200mL) The precipitates were collected by fil-tration and washed with cold water followed by cold MeOHThe resulting chalcones were recrystallized from CHCl

3and

obtained in good yield (60ndash83) (Table 1) Spectral data (IR1H-NMR and MS) of all the newly synthesized chalconeswere in full agreement with the proposed structures

2-(2-Chloroquinoline-3-yl-methylene)-cyclopentanone IR(KBr) cmminus1 1648 (C=O) 1592 (C=C) 1H-NMR (CDCl

3) 120575

144 (2H m ndashCH2) 196 (2H t ndashCH

2) 294 (2H t ndashCH

2)

726 (1H s =CH-ylene) 743ndash833 (5H quinoline Ar-H) MS(mz) 257 (M+ 100)2-(2-Chloroquinoline-3-yl-methylene)-cyclohexanone IR (KBr)cmminus1 1656 (C=O) 1562 (C=C) 1H-NMR (CDCl

3) 120575 161 (2H

m ndashCH2) 196 (2H t ndashCH


2) 312 (2H s

ndashCH2) 627 (1H s =CH-ylene) 743ndash833 (5H quinoline Ar-

H) MS (mz) 271 (M+ 100)3-(2-Chloroquinoline-3-yl)-1-(4-nitrophenyl)-propenone IR(KBr) cmminus1 1644 (C=O) 1542 (C=C) 1H-NMR (CDCl

3)

120575 807ndash838 (4H Ar-H) 756 (1H d 119869 = 158) 790 (1H d119869 = 158) 713ndash850 (5H quinoline Ar-H) MS (mz) 338(M+ 100)3-(2-Chloroquinoline-3-yl)-1-phenyl Propenone IR (KBr)cmminus1 1654 (C=O) 1581 (C=C) 1H-NMR (CDCl

3) 120575 745ndash

781 (5H Ar-H) 760 (1H d 119869 = 158) 782 (1H d 119869 = 158)723ndash792 (5H quinoline Ar-H) MS (mz) 293 (M+ 100)2-(2-Nitroquinoline-3-yl-methylene)-cyclopentanone IR (KBr)cmminus1 1650 (C=O) 1560 (C=C) 1H-NMR (CDCl

3) 120575 141 (2H



2) 751 (1H s

=CH-ylene) 770ndash882 (5H quinoline Ar-H) MS (mz) 268(M+ 100)

Journal of Chemistry 3

2-(2-Nitroquinoline-3-yl-methylene)-cyclohexanone IR (KBr)cmminus1 1656 (C=O) 1553 (C=C) 1H-NMR (CDCl

3) 120575 153 (2H



2) 305 (2H

s ndashCH2) 661 (1H s =CH-ylene) 741ndash827 (5H quinoline

Ar-H) MS (mz) 282 (M+ 100)1-(4-Nitrophenyl)-3-(2-nitroquinolin-3-yl)-propenone IR (KBr)cmminus1 1654 (C=O) 1548 (C=C) 1H-NMR (CDCl

3) 120575 821ndash

848 (4H Ar-H) 751 (1H d 119869 = 158) 785 (1H d 119869 = 158)711ndash851 (5H quinoline Ar-H) MS (mz) 349 (M+ 100)3-(2-Nitroquinolin-3-yl)-1-phenyl Propenone IR (KBr) cmminus11656 (C=O) 1587 (C=C) 1H-NMR (CDCl

3) 120575 721ndash773 (5H

Ar-H) 751 (1H d 119869 = 158) 790 (1H d 119869 = 158) 729ndash776(5H quinoline Ar-H) MS (mz) 304 (M+ 100)2-(2-Bromo-quinoline-3-yl-methylene)-cyclopentanone IR(KBr) cmminus1 1665 (C=O) 1590 (C=C) 1H-NMR (CDCl

3) 120575



2)

750 (1H s =CH-ylene) 748ndash860 (5H quinoline Ar-H) MS(mz) 301 (M+ 100)2-(2-Bromo-quinoline-3-yl-methylene)-cyclohexanone IR(KBr) cmminus1 1656 (C=O) 1553 (C=C) 1H-NMR (CDCl

3) 120575



2)

311 (2H s ndashCH2) 626 (1H s =CH-ylene) 748ndash854 (5H

quinoline Ar-H) MS (mz) 315 (M+ 100)3-(2-Bromoquinolin-3-yl)-1-(4-nitrophenyl)-propenone IR(KBr) cmminus1 1634 (C=O) 1556 (C=C) 1H-NMR (CDCl

3)

120575 801ndash824 (4H Ar-H) 758 (1H d 119869 = 158) 792 (1H d119869 = 158) 745ndash816 (5H quinoline Ar-H) MS (mz) 382(M+ 100)3-(2-Bromoquinolin-3-yl)-1-phenyl Propenone IR (KBr)cmminus1 1645 (C=O) 1556 (C=C) 1H-NMR (CDCl

3) 120575 742ndash

784 (5H Ar-H) 743 (1H d 119869 = 158) 776 (1H d 119869 = 158)765ndash786 (5H quinoline Ar-H) MS (mz) 338 (M+ 100)

4 Antibacterial Screening

Antimicrobial activity was carried out by cup-plate agardiffusion method at a concentration of 50120583gmL in solventDMF The purified products were screened for their antibac-terial activity The nutrient agar slant prepared by the usualmethod was incubated at 37 plusmn 5∘C for 24 h The zone ofinhibition was measured in mm The antimicrobial activityof the synthesized compounds was compared with standarddrugs

All series of compounds nearly exhibit the same antimi-crobial activities against all the four bacterial strains thatis B subtilis B pumilius E coli and S aureus (Table 2)Among all series of compounds 1a 2b and 3c exhibitstrong antibacterial activity Introduction of aromatic ketoneincreases the activity against all microorganisms It is furtherincreased by the incorporation of NO

2group at the fourth

position of aromatic ketone Amongst the aliphatic ketonefive membered compounds show decrease in activity (1andash1c)in comparison with six membered compounds (2bndash2d) Ingeneral aromatic introduction in the compounds enhancesthe activity while activity is suppressed by introduction ofaliphatic group in the compounds

Table 2 Antimicrobial activity of synthesized compounds

Zone (mm)(50120583g)

Compounds1a 1b 1c 1d 2a 2b 2c 2d 3a 3b 3c 3d

B subtilis 4 5 5 6 4 6 5 5 5 4 6 5B pumilus 4 5 5 5 mdash 5 5 mdash 5 5 7 5E coli 4 4 4 4 4 4 4 4 4 mdash 4 5S aureus mdash mdash mdash 5 mdash 5 4 6 5 4 4 6

Table 3 Antifungal activity of synthesized compounds

Zone (mm) Compounds1a 1b 1c 1d 2a 2b 2c 2d 3a 3b 3c 3d

Curvulariaeragrostidis 10 08 09 16 08 06 12 09 10 12 08 10

Drechsleratetramera 12 14 12 02 12 08 10 13 08 10 07 11

Fusariumciceri 14 10 11 12 10 12 12 12 15 11 15 16

Bipolarissorokiniana 07 14 06 16 06 06 16 07 12 13 16 05

5 Antifungal Screening

The antifungal activities of the compounds 1andashd 2andashd and3andashd have been assayed at the concentration of 200120583gdiscassays against four plants pathogenic and moulds fungiThe inhibitory effects of compounds against these organismsare given in Table 3 The screening results indicate that thecompound shows good to moderate antifungal activities tothe tested fungi against Curvularia eryostides Drechesleratetrameda Fusarium cicerg and Bipolaris sorokenia

All the compounds show promising antifungal activityagainst all fungi except Bipolaris sorokiniana (Table 3) All thecompounds show strong activity against Drechslera tetram-era and Fusarium ciceri compared with that of the othertwo fungi As in the case of antimicrobial introduction ofaromatic group enhances the activity of 2c 2d 3c and 3dIntroduction of NO

2group at fourth position increases the

activity of 1c 2c and 3cIntroduction of electron withdrawing group shows re-

markable difference in biological activity (both antimicrobialand antifungal)

No systematic change has been observed in antibacterialand antifungal activity for the rest of the compounds

6 Conclusion

All the synthesized compounds were characterized with theirphysical and spectral data The antifungal and antibacterialscreening of the synthesized pyrazolines were found to beactive

This research study reports the successful synthesis ofnew heteroaryl pyrazoline It also reports antimicrobial andantifungal studies of synthesized compounds The biologicalstudy revealed that compounds showed moderate to goodactivity


Acknowledgments

The author is thankful to the Department of ChemistryGovernment Vidarbha Institute of Science amp HumanitiesAmravati Maharashtra India and Director of Garware LabDepartment of Chemistry Pune University Pune for 1HNMR spectral characterization

References

[1] D K Dodiya Studies on heterocyclic compounds of medicinalinterest [PhD thesis] Saurashtra University Gujrat India 2010

[2] A Ganesh ldquoBiological activities of some Pyrazoline deriva-tivesrdquo International Journal of Pharma and Bio Sciences vol l4no 2 pp 727ndash733 2013

[3] O Ruhoglu Z Ozdemir U Calis B Gumusel and A A BilginldquoSynthesis of and pharmacological studies on the antidepressantand anticonvulsant activities of some 135-trisubstituted pyra-zolinesrdquo Arzneimittel-ForschungDrug Research vol 55 no 8pp 431ndash436 2005

[4] S A Thakkar Studies on bioactive heterocycles and othermoieties [PhD thesis] Saurashtra University Gujrat India2010

[5] A Handan A Oznur K Ayse B Seher and O Gulten ldquoSyn-thesis characterization and evaluation of antimicrobial activityof Mannich bases of some 2-[(4-carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinonesrdquo Indian Journal of Chemistry vol44B p 585 2005

[6] J T Desai C K Desai and K R Desai ldquoA convenient rapidand eco-friendly synthesis of isoxazoline heterocyclic moietycontaining bridge at 2∘-amine as potential pharmacologicalagentrdquo Journal of the Iranian Chemical Society vol 5 no 1 pp67ndash73 2008

[7] V Klimesova M Otcenasek and K Waisser ldquoPotential anti-fungal agents Synthesis and activity of 2-alkylthiopyridine-4-carbothioamidesrdquo European Journal of Medicinal Chemistryvol 31 no 5 pp 389ndash395 1996

[8] E Suloeva M Yure E Gudriniece M Petrova and A GutcaitsldquoSynthesis of 23-dihydroimidazo-[12-a]pyridines from 13-diketonesrdquo Chemistry of Heterocyclic Compounds vol 37 no 7pp 872ndash875 2001

[9] J M Quintela C Peinador L Botana M Estevez and RRiguera ldquoSynthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[23-d]-pyrimidinesrdquo Bioorganicand Medicinal Chemistry vol 5 no 8 pp 1543ndash1553 1997

[10] B Abarca I Alkorta R Ballesteros et al ldquo3-(2-Pyridyl)-[123]triazolo[15-a]pyridines An experimental and theoretical(DFT) study of the ring-chain isomerizationrdquo Organic andBiomolecular Chemistry vol 3 no 21 pp 3905ndash3910 2005

[11] B Abarca R Ballesteros andM Chadlaoui ldquoSynthesis of novelpolypyridylcarbonylpyridines from triazolopyridines Buildingblocks in supramolecular chemistryrdquo Arkivoc vol 2008 no 7pp 73ndash83 2008

[12] B Abarca R Ballesteros M Elmasnaouy P DrsquoOcon MD Ivorra and M Valiente ldquoEvaluation and synthesis of 7-arylhydroxymethyltriazolopyridines as potential cardiovascu-lar agentsrdquo ARKIVOC vol 2002 no 10 pp 9ndash13 2002

[13] Y S Sanghvi S B Larson R C Willis R K Robins and GR Revankar ldquoSynthesis and biological evaluation of certain C-4 substituted pyrazolo[34-b]pyridine nucleosidesrdquo Journal ofMedicinal Chemistry vol 32 no 5 pp 945ndash951 1989

[14] M Paller and K Ponzio Chemical Abstracts vol 99 p 158406r1983

[15] M Kidwai P Priya and S Rastogi ldquoReaction of coumarinderivatives with nucleophiles in aqueous mediumrdquo Zeitschriftfur Naturforschung Section B vol 63 no 1 pp 71ndash76 2008

[16] L Prakash R Sharma S Shukla and G R D PharmaziePharmazie vol 48 p 221 1993

[17] J P Raval and K R Desai ldquoSynthesis and antimicrobial activityof new triazolopyridinyl phenothiazinesrdquoARKIVOC vol 2005no 13 pp 21ndash28 2005

[18] A Heichachiro K Shinozaki S Niwa et alChemical Abstractsvol 110 p 23891v 1989

[19] K Bajaj V K Srivastava and A Kumar ldquoSynthesis andpsychotropic evaluation of some new N-substitutedbenzo-thiaoxazepinylphenothiazinesrdquo Indian Journal of ChemistrySection B vol 43 no 1 pp 157ndash161 2004

[20] M N Narule ldquoA facile route to the synthesis of 8-[2-(310158401015840

510158401015840

-dimethyl-4

10158401015840

-ethoxy carbonyl pyrrolyl) hydrazine] substitutedphenothiazines and their biological activityrdquo Journal of Chemi-cal Biological and Physical Sciences vol 2 no 4 pp 1681ndash16872012

[21] M Idries and A L Abeed-Mashkor ldquoSynthesis of new [10h-substitutedphenoxazine-3-Yl)-6-pyrimidin-2-phenylthiolOlaminethiol] pyrrolesrdquo Thi-Qar Medical Journal vol 4 no 4pp 120ndash126 2010

[22] R Dahlbom and T Ekstrand Archive of International Pharma-codynamics vol 159 p 70 1996

[23] C S Weil ldquoOn the construction of tables for moving averageinterpolationrdquo Biometrics vol 8 p 249 1952

[24] B Harpen and M Nidwai ldquoSynthesis characterization of Phe-nothiazinly derivativesrdquo The Journal of the American MedicalAssociation vol 129 pp 1219ndash1222 1945

[25] M Narule J M B Santhakumari and A Shanware ldquoSynthesisof 2-[4-(10H-substituted phenothiazine-3-yl)-6-pyrimidin-2-phenylthiololaminethiol] pyrrolesrdquo E-Journal of Chemistryvol 4 no 1 pp 53ndash59 2007

[26] J D Genzer M N Lewis F H McMillan and J A KingldquoSynthesis and anti-microbial activity of 2-[4-(10-p-chloro-benzyl)phenothiazinyl]-3-substituted aryl-1-onesrdquo Journal ofthe American Chemical Society vol 75 p 2206 1953

[27] L Dushay Revue Canadienne de Biologie vol 20 p 321 1961[28] J R Douglass N F Baker and M W Longwest ldquoSynthesis

and biological activity of N-phenothiazinerdquo American Journalof Veterinary Research vol 17 p 318 1956

[29] O Meth-Cohn B Narine and B Tarnowski ldquoA versatile newsynthesis of quinolines and related fused pyridines Part 5 Thesynthesis of 2-chloroquinoline-3-carbaldehydesrdquo Journal of theChemical Society Perkin Transactions 1 pp 1520ndash1530 1981

[30] F Herencia M L Ferrandiz A Ubeda et al ldquoSynthesis andanti-inflammatory activity of chalcone derivativesrdquo Bioorganicand Medicinal Chemistry Letters vol 8 no 10 pp 1169ndash11741998

[31] T Narender K Venkateswarlu B V Nayak and S Sarkar ldquoAnew chemical access for 31015840-acetyl-41015840-hydroxychalcones usingborontrifluoride-etherate via a regioselective Claisen-Schmidtcondensation and its application in the synthesis of chalconehybridsrdquo Tetrahedron Letters vol 52 no 44 pp 5794ndash57982011

[32] R Li G L Kenyon F E Cohen et al ldquoIn vitro antimalarialactivity of chalcones and their derivativesrdquo Journal of MedicinalChemistry vol 38 no 26 pp 5031ndash5037 1995

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of


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Medicinal ChemistryInternational Journal of


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Applied ChemistryJournal of



Theoretical ChemistryJournal of


Journal of

Spectroscopy

Analytical ChemistryInternational Journal of


Journal of


Quantum Chemistry


Organic Chemistry International

ElectrochemistryInternational Journal of



CatalystsJournal of


POCl3

NHCOCH3

a = b = c = d =

H3C H3C

DMF

NO2

R = H NO2 Br

Cl Cl

H

NN

O

OO

O

O

Ketone

R RR

(andashd)

1andashd 2andashd 3andashd

Scheme 1

Table 1 Physical properties of synthesized compounds

Compound ndashR (andashd) Molecular formula Yield Elemental analysisC H O N Cl Br

1a H a C15H12ClNO 83 6991 (6927) 469 (471) 621 (585) 543 (592) 1376 (1425)1b H b C16H14ClNO 75 7072 (7054) 519 (576) 589 (534) 515 (547) 1305 (1289)1c H c C18H11ClN2O3 71 6382 (6296) 327 (375) 1417 (1476) 827 (775) 1047 (1078)1d H d C18H12ClNO 62 7360 (7310) 412 (437) 545 (520) 477 (525) 1207 (1208)2a NO2 a C15H12N2O3 75 6716 (6725) 451 (425) 1789 (1775) 1044 (1075)2b NO2 b C16H14N2O3 80 6807 (6805) 500 (510) 1700 (1706) 992 (979)2c NO2 c C18H11N3O5 63 6189 (6178) 317 (308) 2290 (2276) 1203 (1238)2d NO2 d C18H12N2O3 64 7105 (7125) 397 (367) 1577 (1596) 921 (912)3a Br a C15H12BrNO 64 5962 (5961) 400 (410) 529 (531) 464 (461) 2644 (2637)3b Br b C16H14BrNO 60 6078 (6067) 446 (467) 506 (510) 443 (412) 2527 (2544)3c Br c C18H11BrN2O3 62 5642 (5612) 289 (287) 1253 (1223) 731 (745) 2085 (2133)3d Br d C18H12BrNO 82 6392 (6390) 358 (360) 473 (465) 414 (420) 2363 (2365)

Amixture of quinoline-3-carbaldehyde (001mol) ketoneandashd (010mol) and aq NaOH (4mL 10) in methanol(50mL) was refluxed for 2 h and the reaction mixture wasthen kept at 0∘C (24 h) Subsequently it was poured onto icecold water (200mL) The precipitates were collected by fil-tration and washed with cold water followed by cold MeOHThe resulting chalcones were recrystallized from CHCl

3and

obtained in good yield (60ndash83) (Table 1) Spectral data (IR1H-NMR and MS) of all the newly synthesized chalconeswere in full agreement with the proposed structures

2-(2-Chloroquinoline-3-yl-methylene)-cyclopentanone IR(KBr) cmminus1 1648 (C=O) 1592 (C=C) 1H-NMR (CDCl

3) 120575



2)

726 (1H s =CH-ylene) 743ndash833 (5H quinoline Ar-H) MS(mz) 257 (M+ 100)2-(2-Chloroquinoline-3-yl-methylene)-cyclohexanone IR (KBr)cmminus1 1656 (C=O) 1562 (C=C) 1H-NMR (CDCl

3) 120575 161 (2H



2) 312 (2H s

ndashCH2) 627 (1H s =CH-ylene) 743ndash833 (5H quinoline Ar-

H) MS (mz) 271 (M+ 100)3-(2-Chloroquinoline-3-yl)-1-(4-nitrophenyl)-propenone IR(KBr) cmminus1 1644 (C=O) 1542 (C=C) 1H-NMR (CDCl

3)

120575 807ndash838 (4H Ar-H) 756 (1H d 119869 = 158) 790 (1H d119869 = 158) 713ndash850 (5H quinoline Ar-H) MS (mz) 338(M+ 100)3-(2-Chloroquinoline-3-yl)-1-phenyl Propenone IR (KBr)cmminus1 1654 (C=O) 1581 (C=C) 1H-NMR (CDCl

3) 120575 745ndash

781 (5H Ar-H) 760 (1H d 119869 = 158) 782 (1H d 119869 = 158)723ndash792 (5H quinoline Ar-H) MS (mz) 293 (M+ 100)2-(2-Nitroquinoline-3-yl-methylene)-cyclopentanone IR (KBr)cmminus1 1650 (C=O) 1560 (C=C) 1H-NMR (CDCl

3) 120575 141 (2H



2) 751 (1H s

=CH-ylene) 770ndash882 (5H quinoline Ar-H) MS (mz) 268(M+ 100)



3) 120575 153 (2H



2) 305 (2H



3) 120575 821ndash


3) 120575 721ndash773 (5H


3) 120575



2)


3) 120575



2)



3)


3) 120575 742ndash








Zone (mm)(50120583g)







Fusariumciceri 14 10 11 12 10 12 12 12 15 11 15 16









6 Conclusion




Acknowledgments


References





















510158401015840

-dimethyl-4

10158401015840























Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of



3) 120575 153 (2H



2) 305 (2H



3) 120575 821ndash


3) 120575 721ndash773 (5H


3) 120575



2)


3) 120575



2)



3)


3) 120575 742ndash








Zone (mm)(50120583g)







Fusariumciceri 14 10 11 12 10 12 12 12 15 11 15 16









6 Conclusion




Acknowledgments


References





















510158401015840

-dimethyl-4

10158401015840























Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


Acknowledgments


References





















510158401015840

-dimethyl-4

10158401015840























Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of










Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of

Documents

Research Article Green Synthesis and In Vitro Biological ...downloads.hindawi.com › journals › jchem › 2013 › 542973.pdf · asitic [ ], antiparkinsonian [ , ], anticonvulsant