Applied Chemical Engineering

Coumarins at the interface of chemistry and biology: Applied approaches to synthesis and bioactivity

Yasser Fakri Mustafa

Department of Pharmaceutical Chemistry, College of Pharmacy, University of Mosul, Mosul, 41001, Iraq

DOI: https://doi.org/10.59429/ace.v8i4.5813

Keywords: coumarin derivatives; synthetic methodologies; biological activity; green chemistry; molecular docking; bioimaging

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Abstract

Background: Coumarins and their derivatives represent a diverse class of bioactive molecules linking synthetic organic chemistry with modern biomedical applications. Their versatile benzopyran-2-one scaffold allows extensive chemical modification, resulting in derivatives with remarkable pharmacological and photophysical properties. Aim: This review aims to summarize advances in the synthesis of coumarin derivatives and to correlate their structural features with biological activities, highlighting their potential as multifunctional agents in applied chemical and biological systems. Methods: An integrative analysis of recent literature was performed, encompassing classical and contemporary synthetic strategies—including cyclization, condensation, cross-coupling, and green catalytic methods—and their optimization through computational tools such as molecular docking and quantitative structure–activity relationship modeling. Results: The reviewed data reveal that substitution patterns on the coumarin nucleus critically modulate biological activity across a wide range of pharmacological targets. Derivatives exhibit potent anticancer, antimicrobial, antiviral, antifungal, neuroprotective, and cardioprotective effects. Light-responsive and fluorescent coumarins also serve as effective photosensitizers, bioimaging probes, and targeted drug-delivery systems. Environmentally friendly synthetic methodologies and mechanistic modeling further expand the practical applications of these molecules. Conclusion: The integration of synthetic innovation, biological evaluation, and computational prediction underscores coumarins as privileged scaffolds at the interface of chemistry and biology. Continued interdisciplinary research is expected to drive the rational design of safer, more selective coumarin-based therapeutics and functional materials for future biomedical and technological applications.

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[122]. Faisal AF, Mustafa YF. Capsicum in Clinical Biochemistry: Insights into its Role in Health and Disease. Indian Journal of Clinical Biochemistry. 2025; https://doi.org/10.1007/s12291-025-01317-0

[123]. Lafitte D, Lamour V, Tsvetkov PO, Makarov AA, Klich M, Deprez P, Moras D, Briand C, Gilli R. DNA Gyrase Interaction with Coumarin-Based Inhibitors: The Role of the Hydroxybenzoate Isopentenyl Moiety and the 5‘-Methyl Group of the Noviose. Biochemistry. 2002;41(23):7217–23.

[124]. Malviya J, Alameri AA, Al-Janabi SS, Fawzi OF, Azzawi AL, Obaid RF, Alsudani AA, Alkhayyat AS, Gupta J, Mustafa YF, Karampoor S, Mirzaei R. Metabolomic profiling of bacterial biofilm: trends, challenges, and an emerging antibiofilm target. World Journal of Microbiology and Biotechnology. 2023;39(8):212.

[125]. Alshaher MM, Mustafa YF. Linear pyranocoumarins are potential dazzling dancers between nature, chemistry, and clinical application. Vol. 5, Phytomedicine Plus. 2025. p. 100785.

[126]. Alshaher MM, Mustafa YF. Synthesis of triclosan-derived coumarins as potent, biocompatible, broad-spectrum antimicrobial agents. Applied Chemical Engineering. 2024;7(4):5579.

[127]. Sharapov AD, Fatykhov RF, Khalymbadzha IA, Zyryanov G V., Chupakhin ON, Tsurkan M V. Plant Coumarins with Anti-HIV Activity: Isolation and Mechanisms of Action. Vol. 24, International Journal of Molecular Sciences. 2023.

[128]. Hassan DA, Mustafa YF. Linear furanocoumarins: Bridging natural wisdom and synthetic ingenuity in drug discovery. Phytomedicine Plus. 2025;5:100832.

[129]. Mali G, Maji S, Chavan KA, Shukla M, Kumar M, Bhattacharyya S, Erande RD. Effective Synthesis and Biological Evaluation of Functionalized 2,3-Dihydrofuro[3,2- c ]coumarins via an Imidazole-Catalyzed Green Multicomponent Approach. ACS Omega. 2022;7(40):36028–36.

[130]. Alandijany TA, El-Daly MM, Tolah AM, Bajrai LH, Khateb AM, Alsaady IM, Altwaim SA, Dubey A, Dwivedi VD, Azhar EI. Investigating the Mechanism of Action of Anti-Dengue Compounds as Potential Binders of Zika Virus RNA-Dependent RNA Polymerase. Viruses. 2023;15(7):1501.

[131]. Mustafa YF. New Coumarin Hybrids from Chloramphenicol: A Step Towards Next-Generation Biocompatible Antimicrobials. Russian Journal of Bioorganic Chemistry. 2025;51(5):2274–87.

[132]. Faisal AF, Mustafa YF. Chili pepper: A delve into its nutritional values and roles in food-based therapy. Food Chemistry Advances. 2025;6:100928.

[133]. Alves AMCV, Cruz-Martins N, Rodrigues CF. Marine Compounds with Anti-Candida sp. Activity: A Promised “Land” for New Antifungals. Journal of Fungi. 2022;8(7):669.

[134]. Faisal AF, Mustafa YF. The Multifaceted Chemistry of Chili Peppers: A Biodiversity Treasure for Nutrition and Biomedicine. Chemistry & Biodiversity. 2025;e202402690.

[135]. Prusty JS, Kumar A. Coumarins: antifungal effectiveness and future therapeutic scope. Molecular Diversity. 2020;24(4):1367–83.

[136]. Zeki NM, Mustafa YF. Synthesis of Novel Dioxathiole-6,7-coumarin Hybrids As Cytosafe-Multifunctional Applicants: An In Vitro—In Silico Study. Russian Journal of Bioorganic Chemistry. 2024;50(5):2076–91.

[137]. Younes HA, Mustafa YF. Sweet Bell Pepper: A Focus on Its Nutritional Qualities and Illness‑Alleviated Properties. Indian Journal of Clinical Biochemistry. 2024;39:459–69.

[138]. Al-Rashidi RR, Noraldeen SAM, Kareem AK, Mahmoud AK, Kadhum WR, Ramírez-Coronel AA, Iswanto AH, Obaid RF, Jalil AT, Mustafa YF, Nabavi N, Wang Y, Wang L. Malignant function of nuclear factor-kappaB axis in prostate cancer: Molecular interactions and regulation by non-coding RNAs. Pharmacological Research. 2023;194:106775.

[139]. Kasim SM, Al-Dabbagh BM, Mustafa YF. A review on the biological potentials of carbazole and its derived products. Eurasian Chemical Communications. 2022;4(6):495–512.

[140]. Yang Y, Bustani GS, Alawsi T, Altalbawy FMA, Kareem AK, Gupta J, Zhu P, Hjazi A, Alawadi AH, Mustafa YF. The cardioprotective effects of cerium oxide nanoparticles against the poisoning generated by aluminum phosphide pesticide: Controlling oxidative stress and mitochondrial damage. Pesticide Biochemistry and Physiology. 2023;197:105701.

[141]. Mustafa YF, Mohammed ET, Khalil RR. Synthesis, characterization, and anticoagulant activity of new functionalized biscoumarins. Egyptian Journal of Chemistry. 2021;64(8):4461–8.

[142]. Najmanova I, Dosedel M, Hrdina R, Anzenbacher P, Filipsky T, Riha M, Mladenka P. Cardiovascular Effects of Coumarins Besides their Antioxidant Activity. Current Topics in Medicinal Chemistry. 2015;15(9):830–49.

[143]. Dhalla NS, Ostadal P, Tappia PS. Involvement of Oxidative Stress in Mitochondrial Abnormalities During the Development of Heart Disease. Biomedicines. 2025;13(6):1338.

[144]. Saadati F, Modarresi Chahardehi A, Jamshidi N, Jamshidi N, Ghasemi D. Coumarin: A natural solution for alleviating inflammatory disorders. Current Research in Pharmacology and Drug Discovery. 2024;7:100202.

[145]. Mergia Terefe E, Catalan Opulencia MJ, Rakhshani A, Ansari MJ, Sergeevna SE, Awadh SA, Polatova DS, Abdulkadhim AH, Mustafa YF, Kzar HH, Al-Gazally ME, Kadhim MM, Taherian G. Roles of CCR10/CCL27–CCL28 axis in tumour development: mechanisms, diagnostic and therapeutic approaches, and perspectives. Expert Reviews in Molecular Medicine. 2022;24:e37.

[146]. Margiana R, Hammid AT, Ahmad I, Alsaikhan F, Turki Jalil A, Tursunbaev F, Umar F, Romero Parra RM, Fakri Mustafa Y. Current Progress in Aptasensor for Ultra-Low Level Monitoring of Parkinson’s Disease Biomarkers. Critical Reviews in Analytical Chemistry. 2024;54(3):617–32.

[147]. Fakri Mustafa Y. Coumarins in applied chemical engineering: From natural scaffolds to functional materials. Applied Chemical Engineering. 2025;8(2):5697.

[148]. Hjazi A, Ghaffar E, Asghar W, Alauldeen Khalaf H, Ikram Ullah M, Mireya Romero-Parra R, Hussien BM, Abdulally Abdulhussien alazbjee A, Singh Bisht Y, Fakri Mustafa Y, Reza Hosseini-Fard S. CDKN2B-AS1 as a novel therapeutic target in cancer: Mechanism and clinical perspective. Biochemical Pharmacology. 2023;213:115627.

[149]. Abdulaziz NT, Mustafa YF. The Effect of Heat Variable on the Chemical Composition and Bioactivities of a Citrullus lanatus Seed Aqueous Extracts. Journal of Medicinal and Chemical Sciences. 2022;5(7):1166–76.

[150]. Alam MM, Al-Bahrani HA, Khujaniyozova O, Ali FA, Polatova D, Kholmurodova D, Kuryazov R, Alsalim M, Kuldasheva S, Al-Rashedi NAM, Karamova N, Abomughaid MM, Mustafa YF, Urazbaeva D. Influence of machine learning technology on the development of electrochemical, optical, and image analysis-based methods for biomedical, food, and environmental analysis. Microchemical Journal. 2025;218:115407.

[151]. Al-Hawary SIS, Saleh EAM, Hadrawi SK, Alkhafaji AT, Tuxtayev J, Sain DK, Juyal A, Alkhayyat MRR, Alsaalamy AH, Mustafa YF. New frontiers and prospects of MXene-based photoelectrochemical sensing system for detection of pollutant in food and environment. Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2024;680:132568.

[152]. Xie J, Wang L, Su X, Rodrigues J. Coumarin-based Fluorescent Probes for Bioimaging: Recent Applications and Developments. Current Organic Chemistry. 2021;25(18):2142–54.

[153]. Ban AA, Ibrahim BY, Mustafa YF. The Protective Role of Natural Coumarins Derivatives and Anpro Supplement Against Aflatoxin B1 Pollution in the Quails Coturnix Japonica Diet. Mesopotamia Journal of Agriculture. 2023;51(1):1–13.

[154]. Mustafa YF, Alshaher, Marwa Mohammed Hassan DA, Faisal AF. Synthesis and Medicinal Impacts of Novel 3 , 3 ′ -Bihalocoumarins and Their Precursors , 7-Halocoumarin-3-acetic Acids. Russian Journal of Bioorganic Chemistry. 2025;51(2):802–15.

[155]. Ramírez-Coronel AA, Alameri AA, Altalbawy F, Sanaan Jabbar H, Lateef Al-Awsi GR, Iswanto AH, Altamimi AS, Shareef Mohsen K, Almulla AF, Mustafa YF. Smartphone-Facilitated Mobile Colorimetric Probes for Rapid Monitoring of Chemical Contaminations in Food: Advances and Outlook. Critical Reviews in Analytical Chemistry. 2024;54(7):2290–308.

[156]. Sharma A, Verwilst P, Li M, Ma D, Singh N, Yoo J, Kim Y, Yang Y, Zhu JH, Huang H, Hu XL, He XP, Zeng L, James TD, Peng X, Sessler JL, Kim JS. Theranostic Fluorescent Probes. Chemical Reviews. 2024;124(5):2699–804.

[157]. Abdelbasset WK, Savina SV, Mavaluru D, Shichiyakh RA, Bokov DO, Mustafa YF. Smartphone based aptasensors as intelligent biodevice for food contamination detection in food and soil samples: Recent advances. Talanta. 2023;252:123769.

[158]. Achmad H, Mazin Al-Hamdani M, Abdul-Jabbar Ali S, Kareem AK, Al-Gazally ME, Alexis Ramírez-Coronel A, Altamimi AS, Abosaooda M, Fakri Mustafa Y, Hayif Jasim Ali S. Recent advances of amino acid-based biosensors for the efficient food and water contamination detection in food samples and environmental resources: A technical and analytical overview towards advanced nanomaterials and biological receptor. Microchemical Journal. 2023;189:108552.

[159]. Hassan DA, Mustafa YF. The Activity-Enhancing Effect of the 1,3-Dioxolane Ring in Biomedicine. Russian Journal of Bioorganic Chemistry. 2025;51(3):991–1010.

[160]. Raya I, Widjaja G, HACHEM K, M.N. R, Ahmed AA, M. Kadhim M, Mustafa YF, Mahmood ZH, Aravindhan S. MnCo2O4/Co3O4 Nanocomposites: Microwave-Assisted Synthesis, Characterization and Photocatalytic Performance. Journal of Nanostructures. 2021;11(4):728–35.

[161]. Jebir MR, Mustafa YF. Kidney stones: natural remedies and lifestyle modifications to alleviate their burden. International Urology and Nephrology. 2024;56(3):1025–33.

[162]. Ismael RN, Mustafa YF, Al-Qazaz HK. Cancer-curative potential of novel coumarins from watermelon princess : A scenario of their isolation and activity. Eurasian Chemical Communications. 2022;4(7):657–72.

[163]. Hammoodi SH, Ismael SS, Mustafa YF. Mutual prodrugs for colon targeting: A review. Eurasian Chemical Communications. 2022;4(12):1251–65.

[164]. Ismael SS, Waheed NAM, Kasim SM, Mustafa YF. Novel Coumarin-Indole Hybrids as Cytotoxic Candidates: Synthesis and Antiproliferative Activity. Pharmacognosy Journal. 2023;15(6):1105–11.

[165]. Mustafa YF. When the gut Speaks: The hidden toll of irritable bowel syndrome on body and mind. Gastroenterology & Endoscopy. 2025;3(3):135–51.

[166]. Ebrahimipour SY, Mirzaei M, Zamani K, Mohamadi M, Ghaffarian-Bahraman A, Ramezanpour S. Characterization and In-vitro release of coumarin from folic acid-conjugated mesoporous silica for targeted cancer therapy. Journal of Molecular Structure. 2025;1330:141502.

[167]. Mustafa YF. Role of Fruit-Derived Antioxidants in Fighting Cancer: A Narrative Review. Indian Journal of Clinical Biochemistry. 2025;40(4):522–39.

[168]. Hassan DA, Mustafa YF. Novel 1,3-dioxolane–coumarin hybrids: From synthesis to pharmacological In Vitro-In Silico profiling. Applied Chemical Engineering. 2025;8(1):5651.

[169]. Mustafa YF, Oglah MK, Bashir MK, Mohammed ET, Khalil RR. Mutual prodrug of 5-ethynyluracil and 5-fluorouracil: Synthesis and pharmacokinetic profile. Clinical Schizophrenia and Related Psychoses. 2021;15(5):1–6.

[170]. Alshaher MM, Mustafa YF. Synthesis of Dioxane-fused Coumarins as a new class of biosafe multifunctional therapeutic candidates : A journey from In Vitro to In Silico prediction. Applied Catalysis B: Environmental. 2025;8(1):5652.

[171]. Mustafa YF, Mohammed NA alwahab. A promising oral 5-fluorouracil prodrug for lung tumor: Synthesis, characterization and release. Biochemical and Cellular Archives. 2021;21(Supp 1):1991–9.

[172]. Li J, Wang Q, Xia G, Adilijiang N, Li Y, Hou Z, Fan Z, Li J. Recent Advances in Targeted Drug Delivery Strategy for Enhancing Oncotherapy. Pharmaceutics. 2023;15(9):2233.

[173]. Mustafa YF, Abdulaziz NT. Hymecromone and its products as cytotoxic candidates for brain cancer : A brief review. NeuroQuantology. 2021;19(7):175–86.

[174]. Son A, Park J, Kim W, Lee W, Yoon Y, Ji J, Kim H. Integrating Computational Design and Experimental Approaches for Next-Generation Biologics. Biomolecules. 2024;14(9):1073.

[175]. Jasim MHM, Mustafa YF. Synthesis of Acetaminophen‐Based Coumarins as Selective COX‐2 Inhibitors: An in vitro‐in silico Study. Chemistry & Biodiversity. 2024;21(10):e202401309.

[176]. Li J, Zhao T, Yang Q, Du S, Xu L. A review of quantitative structure-activity relationship: The development and current status of data sets, molecular descriptors and mathematical models. Chemometrics and Intelligent Laboratory Systems. 2025;256:105278.

[177]. Zeki NM, Mustafa YF. Harnessing Artificial Intelligence to Discover the Therapeutic Potential of Natural Coumarins: A Review Study. Russian Journal of Bioorganic Chemistry. 2025;51(4):1432–52.

[178]. Mehta S, Pathak SR. Insilico Drug Design And Molecular Docking Studies Of Novel Coumarin Derivatives As Anti-Cancer Agents. Asian Journal of Pharmaceutical and Clinical Research. 2017;10(4):335.

[179]. Kasmi R, Hadaji E, Chedadi O, El Aissouq A, Bouachrine M, Ouammou A. 2D-QSAR and docking study of a series of coumarin derivatives as inhibitors of CDK (anticancer activity) with an application of the molecular docking method. Heliyon. 2020;6(8):e04514.

[180]. Mazin Zeki N, M.Z. Othman K, Fakri Mustafa Y. Computational Chemistry: A game-changer in the drug discovery field. Applied Chemical Engineering. 2025;8(1):ACE-5601.

[181]. Faisal AF, Mustafa YF. The role of coumarin scaffold in the chemical engineering of bioactive molecules: A narrative review. Applied Chemical Engineering. 2025;8(1):ACE-5595.

[182]. Mustafa YF, Bashir MK, Oglah MK. Synthesis, antioxidant and antitumor activities of new coumarins grafted to 5-fluorouracil. Caspian Journal of Environmental Sciences. 2022;20(2):359–65.

[183]. Al Abdeen SHZ, Mustafa YF, Mutlag SH. Synthesis of disubstituted anisolodipyronederived ester compounds: The search for new bioactive candidates. Eurasian Chemical Communications. 2022;4(11):1171–83.

[184]. Ahmed BA, Mustafa YF, Ibrahim BY. Isolation and characterization of furanocoumarins from Golden Delicious apple seeds. Journal of Medicinal and Chemical Sciences. 2022;5(4):537–45.

[185]. Patil VM, Gupta SP, Masand N, Balasubramanian K. Experimental and computational models to understand protein-ligand, metal-ligand and metal-DNA interactions pertinent to targeted cancer and other therapies. European Journal of Medicinal Chemistry Reports. 2024;10:100133.

[186]. Mustafa YF. Coumarins as natural aphrodisiacs: Mechanistic insights and future perspectives in male sexual health. Fitoterapia. 2025;187:106928.

[187]. Ansari MJ, Jasim SA, Abed AM, Altimari US, Yasin G, Suksatan W, Oudaha KH, Kadhim MM, Jabbar AH, Mustafa YF. Double chelation of Iron through dimer formation of favipiravir: Density functional theory analysis. Main Group Chemistry. 2022;21(3):875–83.

[188]. Waheed SA, Mustafa YF. The in vitro effects of new albocarbon-based coumarins on blood glucose-controlling enzymes. Journal of Medicinal and Chemical Sciences. 2022;5(6):954–67.

[189]. Mustafa YF, Al-Shakarchi W. The psychotropic potential of coumarins: Mechanisms, efficacy, and future prospects. Environment and Social Psychology. 2025;10(3):3534.

[190]. Zhu L, Zhang L, Yang Z, Pu M, Lei M. A theoretical study of the hydroboration of α,β-unsaturated carbonyl compounds catalyzed by a metal-free complex and subsequent C–C coupling with acetonitrile. New Journal of Chemistry. 2021;45(31):14134–40.

[191]. Abdulaziz NT, Mustafa YF. Anticancer properties of hymecromone-derived compounds: A review. International Journal of Pharmaceutical Research. 2021;13(1):2163–74.

[192]. Mustafa YF, Abdulaziz NT. Anticancer potential of hymecromone-based compounds: A review. Biochemical and Cellular Archives. 2021;21(2):4151–61.

[193]. Al-Shakarchi W, Saber Y, Merkhan MM, Mustafa YF. Sub Chronic Toxicity Study of Coumacines. Pharmacognosy Journal. 2023;15(1):160–4.

[194]. Al-Shakarchi W, Saber Y, Merkhan MM, Mustafa YF. Acute toxicity of coumacines: An in vivo study. Georgian medical news. 2023;(338):126–31.

[195]. Younis MA, Hamid OA, Dhaher R, Saber Y, Al-shakarchi W, Merkhan MM, Mustafa YF. Characterization of the renal safety profiles of coumacines. Pharmakeftiki. 2023;35(4):57–63.

[196]. Maashi MS, Al-Mualm M, Al-Awsi GRL, Opulencia MJC, Al-Gazally ME, Abdullaev B, Abdelbasset WK, Ansari MJ, Jalil AT, Alsaikhan F, Shalaby MN, Mustafa YF. Apigenin alleviates resistance to doxorubicin in breast cancer cells by acting on the JAK/STAT signaling pathway. Molecular Biology Reports. 2022;49:8777–84.

[197]. Anywar G, Muhumuza E. Bioactivity and toxicity of coumarins from African medicinal plants. Frontiers in Pharmacology. 2024;14:1231006.

[198]. Abdelbasset WK, Elkholi SM, Ismail KA, AL-Ghamdi HS, Mironov S, Ridha HSH, Maashi MS, Thangavelu L, Mahmudiono T, Mustafa YF. Mequinol-loaded carboxymethyl cellulose/chitosan electrospun wound dressing as a potential candidate to treat diabetic wounds. Cellulose. 2022;29(14):7863–81.

[199]. Kaplan BLF, Hoberman AM, Slikker W, Smith MA, Corsini E, Knudsen TB, Marty MS, Sobrian SK, Fitzpatrick SC, Ratner MH, Mendrick DL. Protecting Human and Animal Health: The Road from Animal Models to New Approach Methods. Pharmacological Reviews. 2024;76(2):251–66.

[200]. Flores-Morales V, Villasana-Ruíz AP, Garza-Veloz I, González-Delgado S, Martinez-Fierro ML. Therapeutic Effects of Coumarins with Different Substitution Patterns. Molecules. 2023;28(5):2413.