Carbon-SO₃H catalyzed expedient synthesis of new spiro-[indeno[1,2-b]quinoxaline-[11,2′]-thiazolidine]-4′-ones as biologically important scaffold

References

• Wada, K. ; Hazawa, M. ; Takahashi, K. ; Mori, T. ; Kawahara, N. ; Kashiwakura, I . Inhibitory Effects of Diterpenoid Alkaloids on the Growth of A172 Human Malignant Cells. J. Nat. Prod. 2007, 70 , 1854-1858. doi:10.1021/np070270w
   PubMed Web of Science ®Google Scholar
• Zlotin, S. G. ; Churakov, A. M. ; Dalinger, I. L. ; Luk’yanov, O. A. ; Makhova, N. N. ; Sukhorukov, A. Y. ; Tartakovsky, V. A . Recent Advances in Synthesis of Organic Nitrogen-Oxygen Systems for Medicine and Materials Science. Mendeleev Commun. 2017, 27 , 535-546. doi:10.1016/j.mencom.2017.11.001
   Web of Science ®Google Scholar
• Kanagarajan, V. ; Thanusu, J. ; Gopalakrishnan, M . Synthesis and in vitro Microbiological Evaluation of Novel 2,4-Diaryl-3-Azabicyclo[3.3.1]Nonan-9,5′-Spiro-1′,2′,4′-Triazolidine-3′-Thiones. Med. Chem. Res. 2012, 21 , 3965-3972. doi:10.1007/s00044-011-9949-x
   Web of Science ®Google Scholar
• LoRusso, P. M. ; Parchment, R. ; Demchik, L. ; Knight, J. ; Polin, L. ; Dzubow, J. ; Behrens, C. ; Harrison, B. ; Trainor, G. ; Corbett, T. H . Preclinical Antitumor Activity of XK469 (NSC 656889). Invest New Drugs 1998, 16 , 287-296.
   PubMed Web of Science ®Google Scholar
• Kim, Y. B. ; Kim, Y. H. ; Park, J. Y. ; Kim, S. K . Synthesis and Biological Activity of New Quinoxaline Antibiotics of Echinomycin Analogues. Bioorg. Med. Chem. Lett. 2004, 14 , 541-544. doi:10.1016/j.bmcl.2003.09.086
   PubMed Web of Science ®Google Scholar
• Zhao, Z. ; Robinson, R. G. ; Barnett, S. F. ; Jones, D. D. ; Jones, R. E. ; Hartman, G. ; Huber, H. E. ; Duggana, M. E. ; Lindsley, C. W . Development of Potent, Allosteric Dual Akt1 and Akt2 Inhibitors with Improved Physical Properties and Cell Activity. Bioorg. Med. Chem. Lett. 2008, 18 , 49-53. doi:10.1016/j.bmcl.2007.11.015
   PubMed Web of Science ®Google Scholar
• Harmenberg, J. ; Wahren, B. ; Bergman, J. ; Akerfeldt, S. ; Lundblad, L . Antiherpes Virus Activity and Mechanism of Action of Indolo-(2,3-b)Quinoxaline and Analogs. Antimicrob. Agents Chemother. 1988, 32 , 1720-1724. doi:10.1128/AAC.32.11.1720
   PubMed Web of Science ®Google Scholar
• Gazit, A. ; App, H. ; McMahon, G. ; Chen, J. ; Levitzki, A. D. ; Bohmer, F . Tyrphostins. 5. Potent Inhibitors of Platelet-Derived Growth Factor Receptor Tyrosine Kinase: structure-Activity Relationships in Quinoxalines, Quinolines, and Indole Tyrphostins. J. Med. Chem. 1996, 39 , 2170-2177. doi:10.1021/jm950727b
   PubMed Web of Science ®Google Scholar
• Owen, D. R. ; Dodd, P. G. ; Gayton, S. ; Greener, B. S. ; Harbottle, G. W. ; Mantell, S. J. ; Maw, G. N. ; Osborne, S. A. ; Rees, H. ; Ringer, T. J. ; et al. Structure-Activity Relationships of Novel Non-Competitive mGluR1 Antagonists: A Potential Treatment for Chronic Pain. Bioorg. Med. Chem. Lett. 2007, 17 , 486-490. doi:10.1016/j.bmcl.2006.10.015
   PubMed Web of Science ®Google Scholar
• Zhang, Q. ; Zhou, H. ; Zhai, S. ; Yan, B . Natural Product-Inspired Synthesis of Thiazolidine and Thiazolidinone Compounds and Their Anticancer Activities. Curr. Pharm. Des. 2010, 16 , 1826-1842. doi:10.2174/138161210791208983
   PubMed Web of Science ®Google Scholar
• Küçükgüzel, G. ; Kocatepe, A. ; De Clercq, E. ; Sahin, F. ; Güllüce, M . Synthesis and Biological Activity of 4-Thiazolidinones, Thiosemicarbazides Derived from Diflunisal Hydrazide. Eur. J. Med. Chem. 2006, 41 , 353-359. doi:10.1016/j.ejmech.2005.11.005
   PubMed Web of Science ®Google Scholar
• Shih, M. H. ; Ke, F.,Y . Syntheses and Evaluation of Antioxidant Activity of Sydnonyl Substituted Thiazolidinone and Thiazoline Derivatives. Bioorg. Med. Chem. 2004, 12 , 4633-4643. doi:10.1016/j.bmc.2004.06.033
   PubMed Web of Science ®Google Scholar
• Vigorita, M. G. ; Ottana, R. ; Monforte, F. ; Maccari, R. ; Trovato, A. ; Monforte, M. T. ; Taviano, M. F . Synthesis and Antiinflammatory, Analgesic Activity of 3,3′-(1,2-Ethanediyl)-Bis[2-Aryl-4-Thiazolidinone] Chiral Compounds. Part 10. Bioorg. Med. Chem. Lett. 2001, 11 , 2791-2794. doi:10.1016/S0960-894X(01)00476-0
   PubMed Web of Science ®Google Scholar
• Look, G. C. ; Schullek, J. R. ; Holmes, C. P. ; Chinn, J. P. ; Gordon, E. M. ; Gallop, M. A . The Identification of Cyclooxygenase-1 Inhibitors from 4-Thiazolidinone Combinatorial Libraries. Bioorg. Med. Chem. Lett. 1996, 6 , 707-712. doi:10.1016/0960-894X(96)00097-2
   Web of Science ®Google Scholar
• Barreca, M. L. ; Balzarini, J. ; Chimirri, A. ; De Clercq, E. ; De Luca, L. ; Höltje, H. D. ; Höltje, M. ; Monforte, A. M. ; Monforte, P. ; Pannecouque, C. ; et al. Design, Synthesis, Structure-Activity Relationships, and Molecular Modeling Studies of 2,3-Diaryl-1,3-Thiazolidin-4-Ones as Potent anti-HIV Agents. J. Med. Chem. 2002, 45 , 5410-5413. doi:10.1021/jm020977+
   PubMed Web of Science ®Google Scholar
• Diurno, J. M. V. ; Mazzoni, O. ; Piscopo, E. ; Calignano, A. ; Giordano, F. ; Bolognese, A . Synthesis and Antihistaminic Activity of Some Thiazolidin-4-Ones. J. Med. Chem. 1992, 35 , 2910-2912. doi:10.1021/jm00093a025
   PubMed Web of Science ®Google Scholar
• Zhang, X. N. ; Dong, X. ; Wei, Y. ; Shi, M . Access to 2′,3′-Dihydro-1′H-Spiro[Indoline-3,4′-Pyridin]-2-Ones via Amino Acid Derived Phosphine-Catalyzed Asymmetric [4 + 2] Annulation with Easily Available Oxindole-Derived α,β-Unsaturated Imines. Tetrahedron 2014, 70 , 2838-2846. doi:10.1016/j.tet.2014.02.052
   Web of Science ®Google Scholar
• Padmavati, V. ; Sudheer, K. ; Muralikrishna, A. ; Padmaja, A. ; Padmavati, V. ; Sudheer, Muralikrishna, A. ; Padmaja, A . Double Michael Adducts: Source for Spiro Heterocycles. Indian J. Chem. 2015, 54B , 283-289.
   Google Scholar
• Saraswat, P. ; Jeyabalan, G. ; Hassan, M. Z. ; Rahman, M. U. ; Nyola, N. K . Review of Synthesis and Various Biological Activities of Spiro Heterocyclic Compounds Comprising Oxindole and Pyrrolidine Moities. Synth. Commun. 2016, 46 , 1643-1664. doi:10.1080/00397911.2016.1211704
   Web of Science ®Google Scholar
• Joshi, K. C. ; Dandia, A. ; Bhagat, S . Synthesis, 19F NMR Spectral Studies and Antibacterial Evaluation of Some New Fluorine Containing Indole Derivatives. J. Fluorine Chem. 1990, 48 , 169-188. doi:10.1016/S0022-1139(00)80431-5
   Web of Science ®Google Scholar
• Kaminskyy, D. ; Khyluk, D. ; Vasylenko, O. ; Zaprutko, L. ; Lesyk, R . A Facile Synthesis and Anticancer Activity Evaluation of Spiro[Thiazolidinone-Isatin] Conjugates. Sci. Pharm. 2011, 79 , 763-777. doi:10.3797/scipharm.1109-14
   PubMedGoogle Scholar
• Arya, K. ; Rawat, D. S. ; Dandia, A. ; Sasai, H . Brønsted Acidic Ionic Liquids: Green, Efficient and Reusable Catalyst for Synthesis of Fluorinated Spiro [Indole-Thiazinones/Thiazolidinones] as Antihistamic Agents. J. Fluorine Chem. 2012, 137 , 117-122. doi:10.1016/j.jfluchem.2012.03.003
   Web of Science ®Google Scholar
• Rajopadhye, M. ; Popp, F. D . Synthesis and Antileukemic Activity of Spiro[Indoline-3,2′-Thiazolidine]-2,4′-Diones. J. Heterocycl. Chem. 1987, 4 , 1637-1642. doi:10.1002/jhet.5570240627
   Web of Science ®Google Scholar
• Rajopadhye, M. D. ; Popp, F . Potential Anticonvulsants. VII. Synthesis of 5′-Methylspiro[3 H -Indole-3,2′-Thiazolidine]-2,4′(1 H )-Diones. J. Heterocycl. Chem. 1984, 21 , 289-291. doi:10.1002/jhet.5570210203
   Web of Science ®Google Scholar
• Tierney, J . The Formation of 2,3-Disubstituted Thiazolidin-4-Ones from s-α′-Aminomercaptoacetic Acid Derivatives. J. Heterocycl. Chem. 1989, 26 , 997. doi:10.1002/jhet.5570260419
   Web of Science ®Google Scholar
• Sharma, R. C. ; Kumar, D . Synthesis of Some New Thiazolidin-4-Ones as Possible Antimicrobial Agents. J. Chem. Res. (S) 2000, 77 , 492-494.
   Google Scholar
• Holmes, C. P. ; Chinn, J. P. ; Look, G. C. ; Gordon, E. M. ; Gallop, M. A . Strategies for Combinatorial Organic Synthesis: Solution and Polymer-Supported Synthesis of 4-Thiazolidinones and 4-Metathiazanones Derived from Amino Acids. J. Org. Chem. 1995, 60 , 7328-7333. doi:10.1021/jo00127a044
   Web of Science ®Google Scholar
• Srivastava, T. ; Haq, W. ; Katti, S. B . Carbodiimide Mediated Synthesis of 4-Thiazolidinones by One-Pot Three-Component Condensation. Tetrahedron Lett. 2002, 58 , 7619-7624. doi:10.1016/S0040-4020(02)00866-9
   Web of Science ®Google Scholar
• Rawal, R. K. ; Srivastava, T. ; Haq, W. ; Katti, S. B . An Expeditious Synthesis of Thiazolidinones and Tetathiazanones. J. Chem. Res. (s) 2004, 5 , 368-369.
   Google Scholar
• Shah, P. M. ; Patel, M. P . Zinc(II) Chloride Catalyzed One-Pot Synthesis of Some New 4-Thiazolidinone Derivative as Biologically Potent Agents. Indian J. Chem. 2011, 50B , 310-314.
   Google Scholar
• Nagarajan, A. S. ; Kamalraj, S. ; Muthumary, J. ; Reddy, B. S. R . Synthesis of Biologically Active Benzothiazole Substituted Thiazolidinone Derivatives Via Cyclization of Unsymmetrical Imines. Indian J. Chem. 2009, 48B , 1577-1582.
   Google Scholar
• Ghashang, M. ; Taghrir, H. ; Biregan, M. N. ; Heydari, N. ; Azimi, F . Preparation of Novel 2-(2-Oxo-2 H -Chromen-4-yl)-3- Arylthiazolidin-4-One Derivatives Using an Efficient Ionic Liquid Catalyst. J. Sulfur Chem. 2016, 37 , 61-69. doi:10.1080/17415993.2015.1089440
   Web of Science ®Google Scholar
• Taghrir, H. ; Ghashang, M . Preparation of 2,3-Diarylthiazolidin-4-One Derivatives Using Barium Molybdate Nanopowders. Synth. React. Inorg. Metal-Org. Nano-Metal Chem. 2016, 46 , 246-225[InsertedFromOnline. doi:10.1080/15533174.2014.988227
   Web of Science ®Google Scholar
• Angapelly, S. ; Sri Ramya, P. V. ; Rani, R. S. ; Kumar, C. G. ; Kamal, A. ; Arifuddin, M . Ultrasound Assisted, VOSO 4 Catalyzed Synthesis of 4-Thiazolidinones: Antimicrobial Evaluation of Indazole-4-Thiazolidinone Derivatives. Tetrahedron Lett. 2017, 58 , 4632-4637. doi:10.1016/j.tetlet.2017.10.070
   Web of Science ®Google Scholar
• Sani, Y. M. ; Daud, W. M. A. W. ; Abdul, Aziz, A. R . Activity of Solid Acid Catalysts for Biodiesel Production: A Critical Review. Applied Catalysis A: General. 2014, 470 , 140-161. doi:10.1016/j.apcata.2013.10.052
   Web of Science ®Google Scholar
• Van Leeuwen, P . Homogeneous Catalysis; Springer: Kluwer Academic: Netherlands, 2004; pp 1-401.
   Google Scholar
• Sanz, R. ; Miguel, D. ; Martínez, A. ; Alvarez-Gutierrez, J. M. ; Rodriguez, F . Brønsted Acid Catalyzed Propargylation of 1,3-Dicarbonyl Derivatives. Synthesis of Tetrasubstituted Furans. Org. Lett. 2007, 9 , 727-730. doi:10.1021/ol0631298
   PubMed Web of Science ®Google Scholar
• Hara, M. ; Yoshida, T. ; Takagaki, A. ; Takata, T. ; Kondo, J. N. ; Hayashi, S. ; Domen, K . A Carbon Material as a Strong Protonic Acid. Angew. Chem. Int. Ed. Engl. 2004, 43 , 2955-2958. doi:10.1002/anie.200453947
   PubMed Web of Science ®Google Scholar
• Liang, X. Z. ; Zeng, M. F. ; Qi, C. Z . One-Step Synthesis of Carbon Functionalized with Sulfonic Acid Groups Using Hydrothermal Carbonization. Carbon. 2010, 48 , 1844-1848. doi:10.1016/j.carbon.2010.01.030
   Web of Science ®Google Scholar
• Maheshwar, Rao, B. ; Niranjan Reddy, G. ; Vijaikumar Reddy, T. ; Prabhavathi Devi, B. L. A. ; Prasad, R. B. N. ; Yadav, J. S. ; Subba Reddy, B. V . Carbon-SO3H: A Novel and Recyclable Solid Acid Catalyst for the Synthesis of Spiro[4H-Pyran-3,3′-Oxindoles]. Tetrahedron Lett. 2013, 54 , 2466-2471. doi:10.1016/j.tetlet.2013.02.089
   Web of Science ®Google Scholar
• Karnakar, K. ; Murthy, S. N. ; Ramesh, K. ; Nageswar, Y. V. D. ; Reddy, T. V. K. ; Bethala, B. L. A. ; Devi, P. ; Prasad, R. B. N . Revisit to the Biginelli Reaction: A Novel and Recyclable Bioglycerol-Based Sulfonic Acid Functionalized Carbon Catalyst for One-Pot Synthesis of Substituted 3,4-Dihydropyrimidin-2-(1H)-Ones. Tetrahedron Lett. 2012, 53 , 1968-1973.
   Web of Science ®Google Scholar
• Ramesh, R. ; Sankar, G. ; Malecki, J. G. ; Appaswami, L . Carbon-SO3H Derived from Glycerol: A Green Recyclable Catalyst for Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones. J. Iran. Chem. Soc. 2018, 15 , 1-9. doi:10.1007/s13738-017-1202-1
   Web of Science ®Google Scholar
• Zhang, F. ; Li, C. ; Qi, C . Synthesis of 4,8-Dihydro-1H-Pyrazolo[3,4-e][1,4]Thiazepin-7(6H)-One Derivatives by Solid Acid-Catalyzed Multi-Component Reaction in Water. RSC Adv. 2016, 6 , 102924-102930. doi:10.1039/C6RA24310J
   Web of Science ®Google Scholar
• Karnakar, K. ; Narayana Murthy, S. ; Ramesh, K. ; Reddy, K. H. V. ; Nageswar, Y. V. D. ; Chandrakala, U. ; Devi, B. L. A. P. ; Prasad, R. B. N . A Novel One-Pot Synthesis of Spiro[Indoline-3,4′-Pyrazolo[3,4-e][1,4]Thiazepine] Diones Using Recyclable Bioglycerol-Based Sulfonic Acid Functionalized Carbon Catalyst. Tetrahedron Lett. 2012, 53 , 3497-3350. doi:10.1016/j.tetlet.2012.04.122
   Web of Science ®Google Scholar
• Prabhavathi Devi, B. L. A. ; Gangadhar, N. ; Siva, Kumar, K. L. N. ; Shiva, Shanker, K. ; Prasad, R. B. N. ; Sai, Prasad, P. S . Synthesis of sulfonic acid functionalized carbon catalyst from glycerol pitch and its application for tetrahydropyranyl protection/deprotection of alcohols and phenols. J. Mol. Catal. A: Chem. 2011, 345 , 930-935. doi:10.1016/j.molcata.2011.05.025
   Google Scholar
• Liu, P. ; Hao, J. W. ; Mo Li, P. ; Zhang, Z. H . Recent Advances in the Application of Deep Eutectic Solvents as Sustainable Media as Well as Catalysts in Organic Reactions. RSC Adv. 2015, 5 , 48675-48704. doi:10.1039/C5RA05746A
   Web of Science ®Google Scholar
• Lu, J.; Li, X. T.; Ma, E. Q.; Mo, L. P.; Zhang, Z. H. Superparamagnetic CuFeO2 Nanoparticles in Deep Eutectic Solvent: an Efficient and Recyclable Catalytic System for the Synthesis of Imidazo[1,2-a]pyridines. Chem. Cat. Chem. 2014, 6, 2854-2859. doi:10.1002/cctc.201402415
   Google Scholar
• Dandia, A. ; Singh, R. ; Khan, S. ; Kumari, S. ; Soni, P . A Rational Eco-Compatible Design Strategy for Regio- and Diastereoselective Synthesis of Novel Dispiropyrrolidine/Thiapyrrolizidine Hybrids. Tetrahedron Lett. 2015, 56 , 4438-4444. doi:10.1016/j.tetlet.2015.04.130
   Web of Science ®Google Scholar
• Dandia, A. ; Singh, R. ; Joshi, J. ; Kumari, S . An Eco-Compatible Synthesis of Medicinally Important Novel Class of Trispiroheterocyclic Framework Using 2,2,2-Trifluoroethanol as a Reusable Medium. J. Fluorine Chem. 2013, 156 , 283-289. doi:10.1016/j.jfluchem.2013.07.008
   Web of Science ®Google Scholar
• Dandia, A. ; Singh, R. ; Bhaskaran, S. ; Samant, S. D . Versatile Three Component Procedure for Combinatorial Synthesis of Biologically Relevant Scaffold Spiro[Indole-Thiazolidinones] under Aqueous Conditions. Green Chem. 2011, 13 , 1852-1859. doi:10.1039/c0gc00863j
   Web of Science ®Google Scholar
• Dandia, A. ; Singh, R. ; Joshi, J. ; Maheshwari, S. ; Soni, P . Ultrasound Promoted Catalyst-Free and Selective Synthesis of Spiro[Indole-3,4′-Pyrazolo[3,4-e][1,4]Thiazepines] in Aqueous Media and Evaluation of Their anti-Hyperglycemic Activity. RSC Adv. 2013, 3 , 18992-190001. doi:10.1039/c3ra43745k
   Web of Science ®Google Scholar
• CCDC 1541603 contains the supplementary crystallographic datas for this paper. These data can be obtained free of charge from The Cambridge Crystallo-graphic Data Centre via www.ccdc.cam.ac.uk/data_request/cif
   Google Scholar
• Singh, S. P. ; Parmar, S. S. ; Raman, K. ; Stenberg, V. I . Chemistry and Biological Activity of Thiazolidinones. Chem. Rev. 1981, 81 , 175-203. doi:10.1021/cr00042a003
   Web of Science ®Google Scholar
• Bolognese, A. ; Correale, G. ; Manfra, M. ; Lavecchia, A. ; Novellino, E. ; Barone, V . Thiazolidin-4-One Formation. Mechanistic and Synthetic Aspects of the Reaction of Imines and Mercaptoacetic Acid under Microwave and Conventional Heating. Org. Biomol. Chem. 2004, 2 , 2809-2813. doi:10.1039/b405400h
   PubMed Web of Science ®Google Scholar
• Devi, B. ; Katkam, G. S. ; Sai, Prasad, P. ; Jagannadh, B. ; Prasad, R. P . A Glycerol-Based Carbon Catalyst for the Preparation of Biodiesel. ChemSusChem 2009, 2 , 617-620. doi:10.1002/cssc.200900097
   PubMed Web of Science ®Google Scholar
• Abbott, A. P. ; Capper, G. ; Davies, D. L. ; Munro, H. L. ; Rasheed, R. K. ; Tambyrajah, V . Preparation of Novel, Moisture-Stable, Lewis-Acidic Ionic Liquids Containing Quaternary Ammonium Salts with Functional Side Chains. Chem. Commun. 2001, 2010-2011. doi:10.1039/b106357j
   PubMed Web of Science ®Google Scholar