N-Heterocycles: Synthesis and Biological Evaluation PDF
Preview N-Heterocycles: Synthesis and Biological Evaluation
Keshav Lalit Ameta · Ravi Kant · Andrea Penoni · Angelo Maspero · Luca Scapinello Editors N-Heterocycles Synthesis and Biological Evaluation N-Heterocycles · · · Keshav Lalit Ameta Ravi Kant Andrea Penoni · Angelo Maspero Luca Scapinello Editors N-Heterocycles Synthesis and Biological Evaluation Editors KeshavLalitAmeta RaviKant DepartmentofChemistry DepartmentofChemistry ModyUniversityofScience ShriRamswaroopMemorialUniversity andTechnology Lucknow,UttarPradesh,India Lakshmangarh,India AngeloMaspero AndreaPenoni DepartmentofScienceandHigh DepartmentofChemistry Technology UniversityofInsubria UniversityofInsubria Varese,Italy Varese,Italy LucaScapinello DepartmentofScienceandHigh Technology UniversityofInsubria Varese,Italy ISBN978-981-19-0831-6 ISBN978-981-19-0832-3 (eBook) https://doi.org/10.1007/978-981-19-0832-3 ©TheEditor(s)(ifapplicable)andTheAuthor(s),underexclusivelicensetoSpringerNature SingaporePteLtd.2022 Thisworkissubjecttocopyright.AllrightsaresolelyandexclusivelylicensedbythePublisher,whether thewholeorpartofthematerialisconcerned,specificallytherightsoftranslation,reprinting,reuse ofillustrations,recitation,broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,and transmissionorinformationstorageandretrieval,electronicadaptation,computersoftware,orbysimilar ordissimilarmethodologynowknownorhereafterdeveloped. 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The registered company address is: 152 Beach Road, #21-01/04 Gateway East, Singapore 189721, Singapore Preface Azaheterocyclesalwaysplayedavitalroleinbiologicalprocessesandarewidespread asnaturalproducts.Theirskeletonissubstantiallyubiquitousindifferentclassesof bioactivecompounds.Abriefsurveyofthemostactivepharmacophoresshowsthat nitrogen-basedheterocyclesarethemostprevalentformofbiologicallyrelevantsmall molecules. N-heterocycles are well-known scaffolds for compounds that exhibit interesting biological activities: antioxidant, anti-inflammatory, antinociceptive, anticancer. Nitrogen-containing heterocycles are generally diffuse in building blocks and finechemicalsofimmenseresearchinterestbecausetheyarewidelyfoundasnatu- rallyoccurringbioactivecompounds.TheimportanceofN-heterocyclesisessential to develop new methods to enhance their synthetic efficiencies and investigate the effectsoftheirmodificationsonbiologicalpotential.Thefundamentalrelevanceof nitrogen-containing heterocycles in pharmaceuticals cannot be understated, as the presenceofsuchringsystemsincompoundssuchasvitamins,herbicides,antifungal agents,anti-bacterialagents,andanticanceragents.Theimportanceoftheseappli- cationshascreatedanunprecedentedneedformoreefficientsyntheticmethodolo- gies.Thedevelopmentofmoreefficientsyntheticproceduresinthisdirectionisthe needoftheday.Totalsynthesis,asymmetricsynthesis,homogeneousandheteroge- neouscatalysis,multi-componentreactions,greensyntheticapproaches,andbenign environmentaltechniquesareonlyfewexamplesofnovelmethodologiesthatwere introducedduringthedecadesandthatledtheorganicsynthesistoexcellentlevels ofsophistication. Thisbookpresentsanoverviewofrecentadvancementsforthesynthesisofsmall- and medium-sized nitrogen-containing heterocycles, including pyrroles, indoles, pyrimidines, pyridines, pyrrolidines, imidazoles, pyrazoles, pyrazolines, lactams, and1,2,3-triazoles,whicharesignificantscaffoldsforcompoundswithpharmaceu- v vi Preface ticaluses.Thebookalsodiscussesvariouspropertiesandperformanceattributesof azaheterocycles including their bioactivity and synthetic strategies. The book can be a valuable reference for beginners, researchers, and professionals interested in organicsynthesisandmedicinalchemistry. Lakshmangarh,India KeshavLalitAmeta Lucknow,India RaviKant Varese,Italy AndreaPenoni Varese,Italy AngeloMaspero Varese,Italy LucaScapinello Contents 1 Pyridines,DihydropyridinesandPiperidines:AnOutline onSynthesisandBiologicalActivities ........................... 1 KamalKrishnaRajbongshi, BinoyarghaDam, andBhismaKumarPatel 2 Imidazole,Hydantoins,Thiazole,andOxazole:AJourney onSyntheticandBiologicalRelevance ........................... 51 MirtaGladisMondinoandRobertodaSilvaGomes 3 Lactams, Azetidines, Penicillins, and Cephalosporins: AnOverviewontheSynthesisandTheirAntibacterialActivity .... 97 AdilsonBeatriz,MirtaGladisMondino,andDênisPiresdeLima 4 SynthesisandBiologicalImportanceofPyrazole,Pyrazoline, andIndazoleasAntibacterial,Antifungal,Antitubercular, Anticancer,andAnti-inflammatoryAgents ...................... 143 NisheethDesai, DharmpalsinhJadeja, HarshMehta, AshvinkumarKhasiya,KeyurShah,andUnnatPandit 5 AnOverviewontheSynthesisandBiologicalStudiesofSome SevenMemberedHeterocyclicSystems .......................... 191 VniraR.Akhmetova, GuzelR.Khabibullina, andAskhatG.Ibragimov 6 Various Synthetic Strategies and Therapeutic Potential of Thiadiazole, Oxadiazole, Isoxazole and Isothiazole Derivatives ................................................... 221 KishorR.DesaiandBhavinR.Patel 7 Sulfur-ContainingPyrazoles,PyrazolinesandIndazoles .......... 275 VniraR.Akhmetova,NailS.Akhmadiev,andAskhatG.Ibragimov 8 SyntheticApproachofQuinazolinesCandidates ................. 313 VinayKumarSingh,AnjaniKumarTiwari,andMohd.Faheem vii viii Contents 9 AnOverviewofCinnolines,QuinazolinesandQuinoxalines: SynthesisandPharmacologicalSignificance ..................... 331 PratibhaSaini, KrishanKumar, SwatiMeena, DineshKumarMahawar, AnshuDandia, K.L.Ameta, andVijayParewa 10 Pharmacological Significance ofTriazoles andTetrazoles inNeurodegenerativeDisease:AnOverview ..................... 355 PankuriGuptaandAbhaSharma 11 AnInsightintotheSynthesisandPharmacologicalActivities ofIndoles,IsoindolesandCarbazoles ........................... 395 SurendraSaini,KrishanKumar,SavitaMeena,AnshuDandia, K.L.Ameta,andVijayParewa 12 Pyrazoles,IndazolesandPyrazolines:RecentDevelopments andTheirProperties .......................................... 415 ShyamL.Gupta,SurendraSaini,PratibhaSaini,AnshuDandia, K.L.Ameta,andVijayParewa 13 Synthesis of Bioactive Thioxoimidazolidinones, Oxazolidinones,Thioxothiazolidinones,Thiazolidinediones ....... 443 EsmailDoustkhahandFatemehMajidiArlan Editors and Contributors AbouttheEditors Prof. (Dr.) Keshav Lalit Ameta is working as a Professor and Head at the Department of Chemistry, School of Liberal Arts and Sciences, Mody University ofScienceandTechnology,Lakshmangarh,Rajasthan, India. His fields of research are green chemistry and nanotechnology in organic synthesis, heterocyclic and medicinal chemistry. In addition, to this he has keen interests in photocatalysis. Prof. Ameta has published over80researcharticlesinthefieldofsyntheticorganic chemistry, medicinal chemistry, and material science withpublishersofinternationalrepute.Moreover,heis honoredFellowofLinneanSocietyofChemistry(FLS) UKin2021andFellowofIndianChemicalSocietyin 2014.Hehasvastexperienceofteachingbothgraduate and postgraduate level students. Apart from this, he is faculty advisor of American Chemical Society (ACS) chapter and Research and Development coordinator at SLAS,ModyUniversityofScienceandTechnology. ix x EditorsandContributors Dr.RaviKantFRSC(UK),FICS,FLS(UK),presently workingasProfessorofChemistry,FacultyofChemical Sciences with an additional Responsibility of Director ResearchandConsultancy,ShriRamswaroopMemorial University Lucknow-Deva Road Uttar Pradesh India. Frompast21years,involvedinResearchintheareaof bioorganometallics, material science and metalophar- maceutical chemistry along with teaching of Chem- istry/AppliedChemistry/PharmaceuticalandMedicinal Chemistryinundergraduateandpostgraduatestudents ofengineering,scienceandpharmaceuticalsciences.He is the winner of Rashtriya Shiksha Gaurav Puraskar- 2015, Young Scientist Award-2018, and Best Faculty Award-2017 along with many more scientific recogni- tion from across the country. He is an active fellow of Royal Society of Chemistry London, Linnean Society ofLondon,IndianScienceCongressAssociation,Uttar PradeshAcademyofSciences,IndianChemicalSociety, Chemical Research Society of India and Centre for EducationalGrowthandResearch. Andrea Penoni is Associate Professor in Organic ChemistryattheDepartmentofScienceandHighTech- nology at the University of Insubria in Como, Italy since 2017. He graduated in Chemistry (1996, laurea degree) and received a Ph.D. in Chemical Sciences (2000, doctoral research) at the University Statale of Milano under the supervision of Prof. Sergio Cenini workingonaprojectonaminationreactionofolefinsand hydrocarbonsusingtransitionmetalcomplexesascata- lysts.HedidhispostdoctoraltrainingattheUniversity StataleofMilano,andthenjoinedtheresearchgroupof Prof.KennethM.Nicholas(2000–2001)attheUniver- sityofOklahoma,wherehestudiedtheannulationreac- tionsbetweennitro-andnitrosoaromaticswithalkynes. Since2003,hehasbeenAssistantProfessorinOrganic Chemistry at the University of Insubria and worked in the research group of Prof. Giovanni Palmisano. His research is particularly focused on the synthesis of nitrogen-containing heterocycles, naturally occur- ring compounds and potentially bioactive molecules. Further, he is involved in research projects on the carbon–nitrogenbondformationmediatedbymetalsand metalcomplexes andsynthesisofbiindolecompounds asinterestingmoietiesinmaterialscience.
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