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2000
Volume 22, Issue 8
  • ISSN: 1570-1794
  • E-ISSN: 1875-6271

Abstract

In recent years, quinolactacins and their derivatives have attracted significant research attention due to their distinctive structural features and intriguing biological properties. These heterocyclic compounds have emerged as promising candidates in medicinal chemistry due to their broad spectrum of therapeutic activities. This review article provides a comprehensive study on recent progress in synthesising and investigating the biological properties of quinolactacins and their diverse analogues, offering insights into the diverse synthetic strategies that have been explored to enhance the efficiency and scalability of their production. The primary emphasis lies on the biological activities exhibited by quinolactacins, including their notable anti-bacterial efficacies, anti-cancer, anti-proliferative, anti-oxidant, anti-malarial, and anti-viral. These compounds have shown great potential as therapeutic agents in the fight against various infectious diseases and cancers, making them promising candidates for drug development. Moreover, this study sheds light on the latest endeavours aimed for the synthesis of quinolactacins and their derivatives. This study serves as a valuable resource for researchers who aim to investigate and further harness the therapeutic potential of quinolactacins and their derivatives in the battle against life-threatening diseases, paving the way for future breakthroughs in drug development.

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2026-02-28

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References

  1. AtanasovA.G. ZotchevS.B. DirschV.M. OrhanI.E. BanachM. RollingerJ.M. BarrecaD. WeckwerthW. BauerR. BayerE.A. MajeedM. BishayeeA. BochkovV. BonnG.K. BraidyN. BucarF. CifuentesA. D’OnofrioG. BodkinM. DiederichM. Dinkova-KostovaA.T. EfferthT. El BairiK. ArkellsN. FanT-P. FiebichB.L. FreissmuthM. GeorgievM.I. GibbonsS. GodfreyK.M. GruberC.W. HeerJ. HuberL.A. IbanezE. KijjoaA. KissA.K. LuA. MaciasF.A. MillerM.J.S. MocanA. MüllerR. NicolettiF. PerryG. PittalàV. RastrelliL. RistowM. RussoG.L. SilvaA.S. SchusterD. SheridanH. Skalicka-WoźniakK. SkaltsounisL. Sobarzo-SánchezE. BredtD.S. StuppnerH. SuredaA. TzvetkovN.T. VaccaR.A. AggarwalB.B. BattinoM. GiampieriF. WinkM. WolfenderJ-L. XiaoJ. YeungA.W.K. LizardG. PoppM.A. HeinrichM. Berindan-NeagoeI. StadlerM. DagliaM. VerpoorteR. SupuranC.T. Natural products in drug discovery: Advances and opportunities.Nat. Rev. Drug Discov.202120320021610.1038/s41573‑020‑00114‑z 33510482
     [Google Scholar]
  2. LiG. LouH.X. Strategies to diversify natural products for drug discovery.Med. Res. Rev.20183841255129410.1002/med.21474 29064108
     [Google Scholar]
  3. LouieK.B. KosinaS.M. HuY. OtaniH. de RaadM. KuftinA.N. Mass spectrometry for natural product discovery.Comprehensive Nat. Prod2020III263306
     [Google Scholar]
  4. Chapter 12.Stud Nat. Prod Chem.201962433453
     [Google Scholar]
  5. ParkS.J. ChoK.N. KimW.G. LeeK.I. An expedient synthesis of (+)-quinolactacin A2.Tetrahedron Lett.200445488793879510.1016/j.tetlet.2004.10.001
     [Google Scholar]
  6. LiP. LuH. ZhangY. ZhangX. LiuL. WangM. LiuL. The natural products discovered in marine sponge-associated microorganisms: Structures, activities, and mining strategy.Front. Mar. Sci.202310119185810.3389/fmars.2023.1191858
     [Google Scholar]
  7. KakinumaN. IwaiH. TakahashiS. HamanoK. YanagisawaT. NagaiK. TanakaK. SuzukiK. KirikaeF. KirikaeT. NakagawaA. QuinolactacinsA. B and C: Novel quinolone compounds from Penicillium sp. EPF-6. I. Taxonomy, production, isolation and biological properties.J. Antibiot.200053111247125110.7164/antibiotics.53.1247 11213284
     [Google Scholar]
  8. SasakiT. TakahashiS. UchidaK. FunayamaS. KainoshoM. NakagawaA. Biosynthesis of quinolactacin A, a TNF production inhibitor.J. Antibiot.200659741842710.1038/ja.2006.59 17025018
     [Google Scholar]
  9. LuL. HuW. TianZ. YuanD. YiG. ZhouY. ChengQ. ZhuJ. LiM. Developing natural products as potential anti-biofilm agents.Chin. Med.20191411110.1186/s13020‑019‑0232‑2 30936939
     [Google Scholar]
  10. ZhuJ. LuY. ChenJ. ChenJ. ZhangH. BaoX. YeX. WangH. Total synthesis of quinolactacin-H from marine-derived Penicillium sp. ENP701 and biological activities.RSC Advances20201041242512425410.1039/D0RA05244B 35516178
     [Google Scholar]
  11. KimW.G. SongN.K. Yoo QuinolactacinsI.D. A1, A2, B1, B2, C1, and C2, novel quinolone alkaloids from Penicillium citrinum.J. Antibiot.198033831835
     [Google Scholar]
  12. M HeraviM. ZadsirjanV. MalmirM. Application of the asymmetric pictet-spengler reaction in the total synthesis of natural products and relevant biologically active compounds.Molecules201823494310.3390/molecules23040943 29670061
     [Google Scholar]
  13. TatsutaK. MisawaH. ChikauchiK. Biomimetic total synthesis of quinolactacin B, TNF production inhibitor, and its analogs.J. Antibiot.200154110911210.7164/antibiotics.54.109 11269706
     [Google Scholar]
  14. ZhangX. JiangW. SuiZ. Concise enantioselective syntheses of quinolactacins A and B through alternative Winterfeldt oxidation.J. Org. Chem.200368114523452610.1021/jo020746a 12762761
     [Google Scholar]
  15. KarolinaP. Pictet-Spengler reactions for the synthesis of pharmaceutically relevant heterocycles. Curr. Opinion in Drug Disc. &.Develop2010136669684
     [Google Scholar]
  16. WaldmannH. SchmidtG. HenkeH. BurkardM. Asymmetric pictet-spengler reactions employing n, n-phthaloyl amino acids as chiral auxiliary groups.Angew. Chem. Int. Ed. Engl.199534212402240310.1002/anie.199524021
     [Google Scholar]
  17. PetersenR.G. KomnatnyyV.V. NielsenT.E. Synthesis of constrained peptidomimetics via the Pictet Spengler reaction.Top. Heterocycl. Chem.2017498110310.1007/7081_2015_190
     [Google Scholar]
  18. Li-NaW. Su-LiS. JinQu. Simple and efficient synthesis of tetrahydro-β-carbolines via the Pictet-Spengler reaction in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP).RSC Advances2020102425124254
     [Google Scholar]
  19. AshariN.A.N. PungotN.H. JaniN.A. ShaameriZ. Efficient synthesis of novel 1-substituted β-carboline derivatives via pictet-spengler cyclization of 5-hydroxy-L-tryptophan.Malaysian. J. Fund. Appl. Sci.202218221822610.11113/mjfas.v18n2.2331
     [Google Scholar]
  20. Ash’ariN.A.N. ShaameriZ. PungotN.H. JaniN.A. Facile synthesis of n-alkylated daibucarboline A derivatives via pictet-spengler condensation of tryptamine.Sci.2021255706715
     [Google Scholar]
  21. AbeM. ImaiT. IshiiN. UsuiM. Synthesis of quinolactacide via an acyl migration reaction and dehydrogenation with manganese dioxide, and its insecticidal activities.Biosci. Biotechnol. Biochem.200670130330610.1271/bbb.70.303 16428857
     [Google Scholar]
  22. AlvaroM. BaldovíV. GarcíaH. MirandaM.A. PrimoaJ. A novel photochemical 1,4-acyl migration in enol esters. The photolysis of enol acetates of 3-phenylpropiophenones.Tetrahedron Lett.198728313613361410.1016/S0040‑4039(00)95549‑7
     [Google Scholar]
  23. ShankaraiahN. da SilvaW.A. AndradeC.K.Z. SantosL.S. Enantioselective total synthesis of (S)-(−)-quinolactacin B.Tetrahedron Lett.200849274289429110.1016/j.tetlet.2008.04.130
     [Google Scholar]
  24. UematsuN. FujiiA. HashiguchiS. IkariyaT. NoyoriR. Asymmetric transfer hydrogenation of imines.J. Am. Chem. Soc.1996118204916491710.1021/ja960364k
     [Google Scholar]
  25. YamakawaM. ItoH. NoyoriR. Mechanism of asymmetric transfer hydrogenation of ketones catalyzed by chiral η6-arene–ruthenium(II) complexes.J. Am. Chem. Soc.200012271466147810.1021/ja991638h
     [Google Scholar]
  26. SantosL.S. PilliR.A. RawalV.H. Enantioselective total syntheses of (+)-arborescidine A, (-)-arborescidine B, and (-)-arborescidine C.J. Org. Chem.20046941283128910.1021/jo035165f 14961682
     [Google Scholar]
  27. MajidM. HeraviS.K. NioushaN. Bischler-Napieralski reaction in the syntheses of isoquinolines.Adv. Heterocycl. Chem.2014112143172
     [Google Scholar]
  28. da SilvaG. MoreiraR. SilvaA.M.S. Chapter 12 - Bioactive quinolactacins and structurally related pyrroloquinolones.Studi Nat. Prod Chem.20196243345310.1016/B978‑0‑444‑64185‑4.00012‑5
     [Google Scholar]
  29. MachteyV. GottliebH.E. BykG. Total synthesis of structures proposed for quinocitrinines A and B and their analogs. Microwave energy as efficient tool for generating heterocycles.ARKIVOC20112011930832410.3998/ark.5550190.0012.923
     [Google Scholar]
  30. KulkarniP.P. KadamA.J. ManeR.B. DesaiU.V. WadgaonkarP.P. Demethylation of methyl aryl ethers using pyridine hydrochloride in solvent-free conditions under microwave irradiation.J. Chem. Res.1999394395
     [Google Scholar]
  31. SaitoK. YoshidaM. UekusaH. DoiT. Facile synthesis of pyrrolyl 4-quinolinone alkaloid quinolactacide by 9-AJ-catalyzed tandem acyl transfer-cyclization of O-alkynoylaniline derivatives.ACS Omega2017284370438110.1021/acsomega.7b00793 31457730
     [Google Scholar]
  32. NagyA. NovákZ. KotschyA. Sequential and domino Sonogashira coupling: Efficient tools for the synthesis of diarylalkynes.J. Organomet. Chem.2005690204453446110.1016/j.jorganchem.2004.12.036
     [Google Scholar]
  33. Sonogashira coupling2021Available from: https://www.organic-chemistry.org/namedreactions/sonogashira-coupling.shtm
  34. JacobsenE.N. Total synthesis of quinolactacin and its biological evaluation.J. Am. Chem. Soc.20041261486914870
     [Google Scholar]
  35. ScharfM.J. ListB. A catalytic asymmetric pictet-spengler platform as a biomimetic diversification strategy toward naturally occurring alkaloids.J. Am. Chem. Soc.202214434154511545610.1021/jacs.2c06664 35976162
     [Google Scholar]
  36. AndresR. WangQ. ZhuJ. Catalytic enantioselective Pictet–Spengler reaction of α-Ketoamides catalyzed by a single H-bond donor organocatalyst.Angew. Chem. Int. Ed.2022611920220178810.1002/anie.202201788 35225416
     [Google Scholar]
  37. IsmailA.Z.H. Mohd ArifP.N.A. RezaliN.S. MohammatM.F. ShaameriZ. Synthetic approaches towards quinolactacin derivatives via diels-alder, acyl migration and multicomponent reactions.Malays. J. Anal. Sci.202226755765
     [Google Scholar]
  38. CaplarV. Total synthesis of quinolactacin and its biological activities.J. Org. Chem.20036852135215
     [Google Scholar]
  39. ZholdassovY.S. YuanL. GarciaS.R. KwokR.W. BoscoboinikA. VallesD.J. MarianskiM. MartiniA. CarpickR.W. BraunschweigA.B. Acceleration of Diels-Alder reactions by mechanical distortion.Science202338066491053105810.1126/science.adf5273 37289895
     [Google Scholar]
  40. YuanY. LiX. DingK. Acid-free aza diels-alder reaction of danishefsky’s diene with imines.Org. Lett.20024193309331110.1021/ol0265822 12227776
     [Google Scholar]
  41. PatelD.B. ParmarJ.A. PatelS.S. NaikU.J. PatelH.D. Recent advances in ester synthesis by Multi-Component Reactions (MCRs): A Review.Curr. Org. Chem.202125553955310.2174/1385272825666210111111805
     [Google Scholar]
  42. ThaiT. SalisburyB.H. ZitoP.M. Ciprofloxacin,2023
     [Google Scholar]
  43. PhamT.D.M. ZioraZ.M. BlaskovichM.A.T. Quinolone antibiotics.MedChemComm201910101719173910.1039/C9MD00120D 31803393
     [Google Scholar]
  44. DobleA. Nalidixic acid. X Pharm.The Compr Pharmacol. Ref200715
     [Google Scholar]
  45. PatonJ.H. ReevesD.S. Fluoroquinolone antibiotics.Drugs198836219322810.2165/00003495‑198836020‑00004 3053126
     [Google Scholar]
  46. What is cancer?2023Available from: https://www.cancer.gov/about-cancer/understanding/what-is-cancer
  47. Cancer.2023Available from: https://www.who.int/health-topics/cancer#tab=tab_1
  48. Cancer - NHS2023Available from: https://www.nhs.uk/conditions/cancer/
  49. What is cancer? cancer.net.2023Available from: https://www.cancer.net/navigating-cancer-care/cancer-basics/what-cancer
  50. KloskowskiT. FrąckowiakS. AdamowiczJ. SzeliskiK. RasmusM. DrewaT. PokrywczyńskaM. Quinolones as a potential drug in genitourinary cancer treatment-a literature review.Front. Oncol.20221289033710.3389/fonc.2022.890337 35756639
     [Google Scholar]
  51. YadavV. TalwarP. Repositioning of fluoroquinolones from antibiotic to anti-cancer agents: An underestimated truth.Biomed. Pharmacother.201911193494610.1016/j.biopha.2018.12.119 30841473
     [Google Scholar]
  52. KloskowskiT. SzeliskiK. FeknerZ. RasmusM. DąbrowskiP. WolskaA. SiedleckaN. AdamowiczJ. DrewaT. PokrywczyńskaM. Ciprofloxacin and levofloxacin as potential drugs in genitourinary cancer treatment-the effect of dose–response on 2D and 3D cell cultures.Int. J. Mol. Sci.202122211197010.3390/ijms222111970 34769400
     [Google Scholar]
  53. HawtinR.E. StockettD.E. BylJ.A.W. McDowellR.S. TanN. ArkinM.R. ConroyA. YangW. OsheroffN. FoxJ.A. Voreloxin is an anticancer quinolone derivative that intercalates DNA and poisons topoisomerase II.PLoS One2010541018610.1371/journal.pone.0010186 20419121
     [Google Scholar]
  54. ScatenaC.D. KumerJ.L. ArbitrarioJ.P. HowlettA.R. HawtinR.E. FoxJ.A. SilvermanJ.A. Voreloxin, a first-in-class anticancer quinolone derivative, acts synergistically with cytarabine in vitro and induces bone marrow aplasia in vivo.Cancer Chemother. Pharmacol.201066588188810.1007/s00280‑009‑1234‑z 20058009
     [Google Scholar]
  55. ZhaoF. LiuZ. YangS. DingN. GaoX. Quinolactacin biosynthesis involves non-ribosomal-peptide-synthetase-catalyzed Dieckmann condensation to form the quinolone-γ-lactam hybrid.Angew. Chem. Int. Ed.20205943191081911410.1002/anie.202005770 32663343
     [Google Scholar]
  56. KyeremehK. OwusuK.B. OfosuheneM. OhashiM. AgyapongJ. CamasA.S. Mustafa CamasM. Anti-proliferative and anti-plasmodial activity of quinolactacin A2, citrinadin a and butrecitrinadin co-isolated from a ghanaian mangrove endophytic fungus cladosporium oxysporum strain BRS2A-AR2F.Journal of chemistry and applications201731011210.13188/2380‑5021.1000007
     [Google Scholar]
  57. KyeremehK. Isolation of quinolactacin derivatives from Cladosporium oxysporum and their biological activities.J. Chem. Pharm. Res.2017934148
     [Google Scholar]
  58. Citrinadin A and butrecitrinadin co-isolated from a ghanaian mangrove endophytic fungus cladosporium oxysporum strain BRS2AAR2F.2023Available from: https://www.researchgate.net/ publication/319230669_Anti-Proliferative_and_Anti-Plasmodia_Activity_of_ Quinolactacin_ A2_ Citrinadin_ A_and_Butrecitrinadin_coisolated_from_a_Ghanaian_Mangrove_Endophytic_ Fungus_Cladosporium_oxysporum_strain_BRS2A-AR2F
  59. MeiyantoE. PutriH. Arum LarasatiY. Yudi UtomoR. Istighfari JenieR. IkawatiM. LestariB. Yoneda-KatoN. NakamaeI. KawaichiM. KatoJ.Y. Anti-proliferative and anti-metastatic potential of curcumin analogue, pentagamavunon-1 (pgv-1), toward highly metastatic breast cancer cells in correlation with ROS generation.Adv. Pharm. Bull.20199344545210.15171/apb.2019.053 31592109
     [Google Scholar]
  60. Malaria.2023Available from: https://www.who.int/newsroom/questions-and-answers/item/malaria?gclid=Cj0KCQjw9fqnBhDSARIsAHlc QYTghNx3SpzLyJxwIMtld6aUzabul1SCxGDBpXRE4HrCOI53DoPTuu8aAo3JEALw_wcB
  61. Malaria.2024Available from: https://www.who.int/news-room/fact-sheets/detail/malaria
  62. HuY.Q. GaoC. ZhangS. XuL. XuZ. FengL.S. WuX. ZhaoF. Quinoline hybrids and their antiplasmodial and antimalarial activities.Eur. J. Med. Chem.2017139224710.1016/j.ejmech.2017.07.061 28800458
     [Google Scholar]
  63. ShamsujunaidiR. SaaidinA.S. AzizM.H.A. MohammatM.F. PungotN.H. Studies on the synthesis of β-carboline and its derivatives as potential antimalarial drug components.Malays. J. Anal. Sci.20232714453
     [Google Scholar]
  64. FanY.L. ChengX.W. WuJ.B. LiuM. ZhangF.Z. XuZ. FengL.S. Antiplasmodial and antimalarial activities of quinolone derivatives: An overview.Eur. J. Med. Chem.201814611410.1016/j.ejmech.2018.01.039 29360043
     [Google Scholar]
  65. Cardiovascular diseases.2023Available from: https://www.who.int/health-topics/cardiovascular-diseases#tab=tab_1
  66. MorisD. SpartalisM. SpartalisE. KarachaliouG.S. KaraolanisG.I. TsourouflisG. TsilimigrasD.I. TzatzakiE. TheocharisS. The role of reactive oxygen species in the pathophysiology of cardiovascular diseases and the clinical significance of myocardial redox.Ann. Transl. Med.201751632610.21037/atm.2017.06.27 28861423
     [Google Scholar]
  67. SinghA. KukretiR. SasoL. KukretiS. Oxidative Stress: A key modulator in neurodegenerative diseases.Molecules2019248158310.3390/molecules24081583 31013638
     [Google Scholar]
  68. CeylanŞ. CebeciY.U. DemirbaşN. BaturÖ.Ö. ÖzakpınarÖ.B. Antimicrobial, antioxidant and antiproliferative activities of novel quinolones.ChemistrySelect2020536113401134610.1002/slct.202002779
     [Google Scholar]
  69. How do free radicals affect the body?2023Available from: https://www.medicalnewstoday.com/articles/318652
  70. ScroggsS.L.P. GassJ.T. ChinnasamyR. WidenS.G. AzarS.R. RossiS.L. ArterburnJ.B. VasilakisN. HanleyK.A. Evolution of resistance to fluoroquinolones by dengue virus serotype 4 provides insight into mechanism of action and consequences for viral fitness.Virology20215529410610.1016/j.virol.2020.09.004 33120225
     [Google Scholar]
  71. GaillardT. MadametM. TsombengF.F. DormoiJ. PradinesB. Antibiotics in malaria therapy: Which antibiotics except tetracyclines and macrolides may be used against malaria?Malar. J.201615155610.1186/s12936‑016‑1613‑y 27846898
     [Google Scholar]
  72. KhanI.A. SiddiquiS. RehmaniS. KazmiS.U. AliS.H. Fluoroquinolones inhibit HCV by targeting its helicase.Antivir. Ther.201217346747610.3851/IMP1937 22293206
     [Google Scholar]
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Recent Advances in the Synthesis and Biological Activities of Quinolactacin and its Derivatives: A Comprehensive Review
Curr. Org. Synth. 22, 883 (2025); https://doi.org/10.2174/0115701794378020250717163142
/content/journals/cos/10.2174/0115701794378020250717163142
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  • Article Type:     Review Article
Keyword(s): anti-bacterial; anti-cancer; anti-viral; Biological activities; heterocyclic compounds; quinolactacin; synthesis route

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