Facile One Pot Synthesis of Acridinediones Using Caffeine Hydrogen Sulfate Catalyst and Their Antimicrobial Evaluation

References

• Pragi Arora, Varun Arora, H. S. Lamba, and Deepak Wadhwa, “Importance of Heterocyclic Chemistry: A Review,” International Journal of Pharmaceutical Sciences and Research 3, no. 9 (2012): 2947.
   Google Scholar
• Madasu Chandrashekhar, Vadithe Lakshma Nayak, Sistla Ramakrishna, and Uppuluri Venkata Mallavadhani, “Novel Triazole Hybrids of Myrrhanone C, a Natural Polypodane Triterpene: Synthesis, Cytotoxic Activity and Cell Based Studies,” European Journal of Medicinal Chemistry 114 (2016): 293–307.
   PubMed Web of Science ®Google Scholar
• Chandrashekhar Madasu, Shailaja Karri, Rajendra Sangaraju, Ramakrishna Sistla, and Mallavadhani Venkata Uppuluri, “Synthesis and Biological Evaluation of Some Novel 1, 2, 3-Triazole Hybrids of Myrrhanone B Isolated from Commiphora mukul Gum Resin: Identification of Potent Antiproliferative Leads Active against Prostate Cancer Cells (PC-3),” European Journal of Medicinal Chemistry 188 (2020): 111974.
   PubMed Web of Science ®Google Scholar
• Madasu Chandrashekhar, Ya-Ming Xu, E. M. Wijeratne, Manping X. Liu, István Molnár, and A. A. Gunatilaka, “Semi-Synthesis and Cytotoxicity Evaluation of Pyrimidine, Thiazole, and Indole Analogues of Argentatins A–C from Guayule (Parthenium argentatum) Resin,” Medicinal Chemistry Research 31 (2022): 1088–1098.
   Web of Science ®Google Scholar
• Uppuluri Venkata Mallavadhani, Madasu Chandrashekhar, Vadithe Lakshma Nayak, and Sistla Ramakrishna, “Vadithe Lakshma Nayak, and Sistla Ramakrishna. "Synthesis and Anticancer Activity of Novel Fused Pyrimidine Hybrids of Myrrhanone C, a Bicyclic Triterpene of Commiphora mukul Gum Resin,” Molecular Diversity 19, no. 4 (2015): 745–57.
   PubMed Web of Science ®Google Scholar
• Ali Dahaghin, Seyedhamidreza Emadiyanrazavi, Mohammad Haghpanahi, Milad Salimibani, Hossein Bahreinizad, Reza Eivazzadeh-Keihan, and Ali Maleki, “A Comparative Study on the Effects of Increase in Injection Sites on the Magnetic Nanoparticles Hyperthermia,” Journal of Drug Delivery Science and Technology 63 (2021): 102542.
   Web of Science ®Google Scholar
• Reza Taheri-Ledari, Wenjie Zhang, Maral Radmanesh, Nicole Cathcart, Ali Maleki, and Vladimir Kitaev, “Plasmonic Photothermal Release of Docetaxel by Gold Nanoparticles Incorporated onto Halloysite Nanotubes with Conjugated 2D8-E3 Antibodies for Selective Cancer Therapy,” Journal of Nanobiotechnology 19, no. 1 (2021): 1–21.
   PubMed Web of Science ®Google Scholar
• Reza Taheri‐Ledari, Wenjie Zhang, Maral Radmanesh, Seyedeh Shadi Mirmohammadi, Ali Maleki, Nicole Cathcart, and Vladimir Kitaev, “Multi‐Stimuli Nanocomposite Therapeutic: Docetaxel Targeted Delivery and Synergies in Treatment of Human Breast Cancer Tumor,” Small 16, no. 41 (2020): 2002733.
   PubMed Web of Science ®Google Scholar
• John A. Joule, “Natural Products Containing Nitrogen Heterocycles—Some Highlights 1990–2015,” Advances in Heterocyclic Chemistry 119 (2016): 81–106.
   Web of Science ®Google Scholar
• Mohammad Nikpassand, and Leila Zare Fekri, “Catalyst-Free Synthesis of Mono and Bis Spiro Pyrazolopyridines in DSDABCO as a Novel Media,” Chemical Methodologies 4, no. 4 (2020): 437–46.
   Google Scholar
• Elham Haddadzadeh, and Mohammad Kazem Mohammadi, “One-Pot Synthesize of Phenyl Phenanthro Imidazole Derivatives Catalyzed by Lewis Acid in the Presence of Ammonium Acetate,” Chemical Methodologies 4, no. 3 (2020): 324–32.
   Google Scholar
• Ahmad Reza Moosavi-Zare, and Hadis AfshAr-Hezarkhani, “Application of [Pyridine-1-SO3H-2-COOH] Cl as an Efficient Catalyst for the Preparation of Hexahyroquinolines,” Eurasian Chemical Communications 2 (2020): 465–74.
   Google Scholar
• Heshmatollah Alinezhad, Mahmoud Tajbakhsh, Behrooz Maleki, and Fereshteh Pourshaban Oushibi, “Acidic Ionic Liquid [H-NP] HSO4 Promoted One-Pot Synthesis of Dihydro-1H-Indeno [1, 2-b] Pyridines and Polysubstituted Imidazoles,” Polycyclic Aromatic Compounds 40, no. 5 (2020): 1485–500.
   Web of Science ®Google Scholar
• Behrooz Maleki, Hadi Natheghi, Reza Tayebee, Heshmatollah Alinezhad, Amirhassan Amiri, Seyed Alireza Hossieni, and Seyed Mohammad Mahdi Nouri, “Synthesis and Characterization of Nanorod Magnetic Co–Fe Mixed Oxides and Its Catalytic Behavior towards One-Pot Synthesis of Polysubstituted Pyridine Derivatives,” Polycyclic Aromatic Compounds 40, no. 3 (2020): 633–43.
   Web of Science ®Google Scholar
• Nusrat Sahiba, Ayushi Sethiya, Jay Soni, and Shikha Agarwal, “Acridine‐1, 8‐Diones: Synthesis and Biological Applications,” ChemistrySelect 6, no. 9 (2021): 2210–51.
   Web of Science ®Google Scholar
• Miyase Gözde Gündüz, Ali Evrim Doğan, Rahime Şimşek, Kevser Erol, and Cihat Şafak, “Substituted 9-Aryl-1, 8-Acridinedione Derivatives and Their Effects on Potassium Channels,” Medicinal Chemistry Research 18, no. 4 (2009): 317–25.
   Web of Science ®Google Scholar
• A. Jamalian, R. Miri, O. Firuzi, M. Amini, A. A. Moosavi-Movahedi, and A. Shafieea, “Synthesis, Cytotoxicity and Calcium Antagonist Activity of Novel Imidazolyl Derivatives of 1, 8-Acridinediones,” Journal of the Iranian Chemical Society 8, no. 4 (2011): 983–91.
   Web of Science ®Google Scholar
• K. B. Ramesh, and M. A. Pasha, “Study on One-Pot Four-Component Synthesis of 9-Aryl-Hexahydro-Acridine-1, 8-Diones Using SiO2–I as a New Heterogeneous Catalyst and Their Anticancer Activity,” Bioorganic & Medicinal Chemistry Letters 24, no. 16 (2014): 3907–13.
   PubMed Web of Science ®Google Scholar
• Gökçe Sevim Öztürk Fincan, Miyase Gözde Gündüz, İsmail Mert Vural, Rahime Şimşek, Yusuf Sarıoğlu, and Cihat Şafak, “Investigation of Myorelaxant Activity of 9-Aryl-3, 4, 6, 7-Tetrahydroacridine-1, 8-(2H, 5H, 9H, 10H)-Diones in Isolated Rabbit Gastric Fundus,” Medicinal Chemistry Research 21, no. 8 (2012): 1817–24.
   Web of Science ®Google Scholar
• Muharrem Kaya, Erhan Basar, Emrah Çakir, Ekrem Tunca, and Metin Bülbül, “Synthesis and Characterization of Novel Dioxoacridine Sulfonamide Derivatives as New Carbonic Anhydrase Inhibitors,” Journal of Enzyme Inhibition and Medicinal Chemistry 27, no. 4 (2012): 509–14.
   PubMed Web of Science ®Google Scholar
• Ibanga Okon Isaac, Mariya Al-Rashida, Shafiq Ur. Rahman, Rima D. Alharthy, Asnuzilawati Asari, Abdul Hameed, Khalid Mohammed Khan, and Jamshed Iqbal, “Acridine-Based (Thio) Semicarbazones and Hydrazones: Synthesis, In Vitro Urease Inhibition, Molecular Docking and In-Silico ADME Evaluation,” Bioorganic Chemistry 82 (2019): 6–16.
   PubMed Web of Science ®Google Scholar
• Manisha R. Bhosle, Moseen A. Shaikh, Dhananjay Nipate, Lalit D. Khillare, Giribala M. Bondle, and Jaiprakash N. Sangshetti, “ChCl: 2ZnCl2 Catalyzed Efficient Synthesis of New Sulfonyl Decahydroacridine-1, 8-Diones via One-Pot Multicomponent Reactions to Discover Potent Antimicrobial Agents,” Polycyclic Aromatic Compounds 40 (2020): 1175–1186.
   Web of Science ®Google Scholar
• Huan Xiong, Jie Han, Jun Wang, Wenchao Lu, Chen Wang, Yu Chen, Naixia Zhang, Yu-Chih Liu, Chenhua Zhang, Hong Ding, et al., “Discovery of 1, 8-Acridinedione Derivatives as Novel GCN5 Inhibitors via High Throughput Screening,” European Journal of Medicinal Chemistry 151 (2018): 740–51.
   PubMed Web of Science ®Google Scholar
• Jacques Joubert, and Erika Kapp, “Discovery of 9-Phenylacridinediones as Highly Selective Butyrylcholinesterase Inhibitors through Structure-Based Virtual Screening,” Bioorganic & Medicinal Chemistry Letters 30, no. 9 (2020): 127075.
   PubMed Web of Science ®Google Scholar
• Abdelkader Naouri, Amar Djemoui, Mouhamad Ridha Ouahrani, Mokhtar Boualem Lahrech, Najet Lemouari, Djenisa H. A. Rocha, Hélio Albuquerque, Ricardo F. Mendes, Filipe A. Almeida Paz, Luisa A. Helguero, et al., “Multicomponent and 1, 3-Dipolar Cycloaddition Synthesis of Triazole-and Isoxazole-Acridinedione/Xanthenedione Heterocyclic Hybrids: Cytotoxic Effects on Human Cancer Cells,” Journal of Molecular Structure 1217 (2020): 128325.
   Web of Science ®Google Scholar
• Khodabakhsh Niknam, Farhad Panahi, Dariush Saberi, and Molki Mohagheghnejad, “Silica‐Bonded S‐Sulfonic Acid as Recyclable Catalyst for the Synthesis of 1, 8‐Dioxo‐Decahydroacridines and 1, 8‐Dioxo‐Octahydroxanthenes,” Journal of Heterocyclic Chemistry 47, no. 2 (2010): 292–300.
   Web of Science ®Google Scholar
• Fatemeh Rashedian, Dariush Saberi, and Khodabakhsh Niknam, “Silica‐Bonded N‐Propyl Sulfamic Acid: A Recyclable Catalyst for the Synthesis of 1, 8‐Dioxo‐Decahydroacridines, 1, 8‐Dioxo‐Octahydroxanthenes and Quinoxalines,” Journal of the Chinese Chemical Society 57, no. 5A (2010): 998–1006.
   Web of Science ®Google Scholar
• Mei Hong, and Guomin Xiao, “FSG-Hf (NPf2)4 Catalyzed, Environmentally Benign Synthesis of 1, 8-Dioxo-Decahydroaridines in Water–Ethanol,” Journal of Fluorine Chemistry 144 (2012): 7–9.
   Web of Science ®Google Scholar
• Abolghasem Davoodnia, Amir Khojastehnezhad, and Niloofar Tavakoli-Hoseini, “Carbon-Based Solid Acid as an Efficient and Reusable Catalyst for the Synthesis of 1, 8-Dioxodecahydroacridines under Solvent-Free Conditions,” Bulletin of the Korean Chemical Society 32, no. 7 (2011): 2243–8.
   Web of Science ®Google Scholar
• Nusrat Sahiba, Ayushi Sethiya, Jay Soni, Pankaj Teli, Ankita Garg, and Shikha Agarwal, “A Facile Biodegradable Chitosan‐SO3H Catalyzed Acridine‐1, 8‐Dione Synthesis with Molecular Docking, Molecular Dynamics Simulation and Density Functional Theory against Human Topoisomerase II Beta and Staphylococcus aureus Tyrosyl‐tRNA Synthetase,” Journal of Molecular Structure 1268 (2022): 133676.
   Web of Science ®Google Scholar
• Imene Amine Khodja, Wassima Ghalem, Zineb Imene Dehimat, Raouf Boulcina, Bertrand Carboni, and Abdelmadjid Debache, “Solvent-Free Synthesis of Dihydropyridines and Acridinediones via a Salicylic Acid–Catalyzed Hantzsch Multicomponent Reaction,” Synthetic Communications 44, no. 7 (2014): 959–67.
   Web of Science ®Google Scholar
• Shuo Cao, Shanshan Zhong, Changfeng Hu, Jie‐Ping Wan, and Chengping Wen, “An Environmentally Benign Catalytic Method for Versatile Synthesis of 1, 4‐Dihydropyridines via Multicomponent Reactions,” Chinese Journal of Chemistry 33, no. 5 (2015): 568–72.
   Web of Science ®Google Scholar
• Shahnaz Rostamizadeh, Asiyeh Amirahmadi, Nasrin Shadjou, and Ali M. Amani, “MCM‐41‐SO3H as a Nanoreactor for the One‐Pot, Solvent‐Free Synthesis of 1, 8‐Dioxo‐9‐Aryl Decahydroacridines,” Journal of Heterocyclic Chemistry 49, no. 1 (2012): 111–5.
   Web of Science ®Google Scholar
• Ardeshir Khazaei, Ahmad Reza Moosavi-Zare, Hadis AfshAr-Hezarkhani, and Vahid Khakyzadeh, “Programming of Fe-Catalyzed Cascade Knoevenagel-Michael-Cyclocondensation Reaction: create out Pseudo Acridine Derivatives under Solvent Free Conditions,” Eurasian Chemical Communications 2 (2020): 27–34.
   Google Scholar
• Behrooz Maleki, Reza Tayebee, Mina Kermanian, and Samaneh Sedigh Ashrafi, “One-Pot Synthesis of 1, 8-Dioxodecahydroacridines and Polyhydroquinoline Using 1, 3-Di (Bromo or Chloro)-5, 5-Dimethylhydantoin as a Novel and Green Catalyst under Solvent-Free Conditions,” Journal of the Mexican Chemical Society 57, no. 4 (2017): 290–7.
   Google Scholar
• Behrooz Maleki, Hengameh Atharifar, Oliver Reiser, and Reihaneh Sabbaghzadeh, “Glutathione-Coated Magnetic Nanoparticles for One-Pot Synthesis of 1, 4-Dihydropyridine Derivatives,” Polycyclic Aromatic Compounds 41, no. 4 (2021): 721–34.
   Web of Science ®Google Scholar
• Reza Eyvazzadeh-Keihan, Negar Bahrami, Reza Taheri-Ledari, and Ali Maleki, “Highly Facilitated Synthesis of Phenyl (Tetramethyl) Acridinedione Pharmaceuticals by a Magnetized Nanoscale Catalytic System, Constructed of GO, Fe3O4 and Creatine,” Diamond and Related Materials 102 (2020): 107661.
   Web of Science ®Google Scholar
• Ali Maleki, “One-Pot Three-Component Synthesis of Pyrido [2′, 1′: 2, 3] Imidazo [4, 5-c] Isoquinolines Using Fe3O4@ SiO2–OSO3 H as an Efficient Heterogeneous Nanocatalyst,” RSC Advances 4, no. 109 (2014): 64169–73.
   Web of Science ®Google Scholar
• Priyanka Kalal, Ayushi Sethiya, Jay Soni, Isha Patel, Divyani Gandhi, and Shikha Agarwal, “Caffeine Hydrogen Sulfate: A Recyclable Solid Acid Catalyst for Mechanochemical Synthesis of 2-Arylbenzothiazoles,” Journal of Sulfur Chemistry 43, no. 3 (2022): 233–41.
   Web of Science ®Google Scholar
• Keshri Nath Tiwari, Mane Rajendra Uttam, Puja Kumari, Piyush Vatsa, and S. M. Prabhakaran, “Efficient Synthesis of Acridinediones in Aqueous Media,” Synthetic Communications 47, no. 10 (2017): 1013–9.
   Web of Science ®Google Scholar