Regioselective synthesis and biological evaluation of novel dispiropyrrolidine derivatives via one-pot four-component reaction

References

• Trost, B. M.; Koester, D. C.; Sharif, E. U. Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes. Chem. Inform. 2016, 28, 47. DOI: 10.1002/chin.201628067.
   Google Scholar
• Ghannay, S.; Bakari, S.; Ghabi, A.; Kadri, A.; Msaddek, M.; Aouadi, K. Stereoselective Synthesis of Enantiopure N-Substituted Pyrrolidin-2,5-Dione Derivatives by 1,3-Dipolar Cycloaddition and Assessment of Their In Vitro Antioxidant and Antibacterial Activities. Bioorg. Med. Chem. Lett. 2017, 27, 2302–2307. DOI: 10.1016/j.bmcl.2017.04.044.
   PubMed Web of Science ®Google Scholar
• Ang, C. W.; Mohamed, A. A.; Yeong, K. Y.; Rusli, I.; Tan, S. C.; Raju, S. K. A Facile Three-Component [3 + 2]-Cycloaddition for the Regioselective Synthesis of Highly Functionalised Dispiropyrrolidines Acting as Antimycobacterial Agents. Bioorg. Med. Chem. Lett. 2013, 23, 1383–1386. DOI: 10.1016/j.bmcl.2012.12.069.
   PubMed Web of Science ®Google Scholar
• Hassan, M. Z.; Mohamed, A. A.; Hasnah, O.; Raju, S. K.; Natarajan, A. Design, Synthesis and Antimycobacterial Activity of Dispiropyrrolidines Derivatives. Med. Chem. (Los Angeles) 2016, 6, 486–491. DOI: 10.4172/2161-0444.1000387.
   Google Scholar
• Kanti, S.; Lokesh, K. S.; Meenakshi, J.; Renuka, J. Design, Synthesis and Antibacterial Activity of Novel Dispiro Heterocycles. Chem. Biol. Interface. 2018, 8, 138–150.
   Google Scholar
• Yang, J.-M.; Hu, Y.; Li, Q.; Yu, F.; Cao, J.; Fang, D.; Huang, Z.-B.; Shi, D.-Q. Efficient and Regioselective Synthesis of Novel Functionalized Dispiropyrrolidines and Their Cytotoxic Activities. ACS Comb. Sci. 2014, 16, 139–145. DOI: 10.1021/co400096c.
   PubMed Web of Science ®Google Scholar
• Abdulrahaman, I. A.; Natarajan, A.; Raju, S. K.; Periasamy, V. S.; Ali, A. A.; Jegan, A. Anti-Cancer Agents. U.S. Patent 9873699 B1 20180123, January 23, 2018.
   Google Scholar
• Hai, L.; Guolan, D.; Daqing, S. Regio- and Stereoselective Synthesis of Novel Dispiropyrrolidine Bisoxindole Derivatives via Multicomponent Reactions. ACS J. Comb. Chem. 2010, 12, 292–294. DOI: 10.1021/cc900195t.
   PubMedGoogle Scholar
• Asadbegi, S.; Bodaghifard, M. A.; Mobinikhaledi, A. Poly N, N-Dimethylaniline-Formaldehyde Supported on Silica-Coated Magnetic Nanoparticles: A Novel and Retrievable Catalyst for Green Synthesis of 2-Amino-3-Cyanopyridines. Res. Chem. Intermed. 2017, 43, 1–15. DOI: 10.1007/s11164-017-3200-4.
   Web of Science ®Google Scholar
• Ardeshir, K.; Maryam, M. G.; Negin, S. Magnetic‐Based Picolinaldehyde–Melamine Copper Complex for the One‐Pot Synthesis of Hexahydroquinolines via Hantzsch Four‐Component Reactions. Appl. Organomet. Chem. 2017, 32, e4151. DOI: 10.1002/aoc.4151.
   Web of Science ®Google Scholar
• Mostafa, K.; Mohammad, R. K.; Firouz, M. M.; Alexander, V.; Peter, L. Ultrasound-Assisted, ZnBr2-Catalyzed Regio- and Stereoselective Synthesis of Novel 3,3′-Dispiropyrrolidine Bisoxindole Derivatives via 1,3-Dipolar Cycloaddition Reaction of an Azomethine Ylide. Arkivocpart v 2017, 5, 20–31. DOI: 10.24820/ark.5550190.p010.046.
   Google Scholar
• Yang, W. L.; Liu, Y. Z.; Luo, S.; Yu, X.; Fossey, J. S.; Deng, W. P. Copper-Catalyzed Asymmetric Construction of Dispiropyrrolidine Skeleton via 1,3-Dipolar Cycloaddition of Azomethine Ylides with α-Alkylidene Succinimides. Chem. Commun. 2015, 51, 9212–9215. DOI: 10.1039/C5CC02362A.
   PubMed Web of Science ®Google Scholar
• Binoyargha, D.; Mithu, S.; Ramen, J.; Amarta Kumar, P. Nano-Ferrite Supported Glutathione as a Reusable Nanoorganocatalyst for the Synthesis of Phthalazine-Trione and Dione Derivatives under Solvent Free Condition. RSC Adv. 2016, 6, 54768–54776. DOI: 10.1039/C6RA06376D.
   Web of Science ®Google Scholar
• Andreas, L.; Erick, M. C. First Total Synthesis of (±)-Strychnofoline via a Highly Selective Ring-Expansion Reaction. J. Am. Chem. Soc. 2002, 124, 14826–14827. DOI: 10.1021/ja027906k.
   PubMed Web of Science ®Google Scholar
• Xiangyu, Z. W.; M. C, J. Enantiospecific, Stereospecific Total Synthesis of the Oxindole Alkaloid Alstonisine. Org. Lett. 2002, 4, 4237–4240. DOI: 10.1021/ol020170b.
   PubMed Web of Science ®Google Scholar
• Martin, J.; Holly, B. K.; John, F. Two New Brominated Tyrosine Derivatives from the Sponge Druinella (= Psammaplysilla) Purpurea. J. Nat. Prod. 1991, 54, 1137–1140. DOI: 10.1021/np50076a040.
   PubMed Web of Science ®Google Scholar
• Yu, S.; Qin, D.; Shangary, S.; Chen, J.; Wang, G.; Ding, K.; McEachern, D.; Qiu, S.; Nikolovska-Coleska, Z.; Miller, R.; et al. Potent and Orally Active Small-Molecule Inhibitors of the MDM2-p53 Interaction. J. Med. Chem. 2009, 52, 7970. DOI: 10.1021/jm901400z.
   PubMed Web of Science ®Google Scholar
• Lundahl, K.; Schut, J.; Schlatmann, J. L.; Paerels, G. B.; Peters, A. Synthesis and Antiviral Activities of Adamantane Spiro Compounds. 1. Adamantane and Analogous Spiro-3′-Pyrrolidines. J. Med. Chem. 1972, 15, 129–132. DOI: 10.1021/jm00272a003.
   PubMed Web of Science ®Google Scholar
• Kornet, M. C.; Thio, A. P. Oxindole-3-Spiropyrrolidines and Piperidines. Synthesis and Local Anesthetic Activity. J. Med. Chem. 1976, 19, 892–898. DOI: 10.1021/jm00229a007.
   PubMed Web of Science ®Google Scholar
• Smith, M. C.; Riskin, B. J. The Clinical Use of Barbiturates in Neurological Disorders. Drugs 1991, 42, 365. DOI: 10.2165/00003495-199142030-00003.
   PubMed Web of Science ®Google Scholar
• Brunton, L. L.; Lazo, J. S.; Keith, L. P. Goodman & Gilman’s the Pharmacological Basis of Therapeutics, 11th ed.; McGraw-Hill, Inc.: New York, 2006.
   Google Scholar
• Abou-Gharbia, M. A.; Doukas, P. H. Synthesis of Tricyclic Arylspiro Compounds as Potential Antileukemic and Anticonvulsant Agents. Heterocycles 2017, 12, 637–640. DOI: 10.3987/R-1979-05-0637.
   Google Scholar
• Grams, F.; Brandstetter, H.; D’Alò, S.; Geppert, D.; Krell, H. W.; Leinert, H.; Livi, V.; Menta, E.; Oliva, A.; Zimmermann, G.; et al. Pyrimidine-2,4,6-Triones: A New Effective and Selective Class of Matrix Metalloproteinase Inhibitors. Biol. Chem. 2001, 382, 1277. DOI: 10.1515/BC.2001.159.
   PubMed Web of Science ®Google Scholar
• Maquoi, E.; Sounni, N. E.; Devy, L.; Oliver, F.; Frankenne, F.; Krell, H. W.; Grams, F.; Foidart, J. M.; Noel, A. Anti-Invasive, Antitumoral, and Antiangiogenic Efficacy of a Pyrimidine-2,4,6-Trione Derivative, an Orally Active and Selective Matrix Metalloproteinases InhibitorClin. Cancer. Res. 2004, 10, 4038. DOI: 10.1158/1078-0432.CCR-04-0125.
   Web of Science ®Google Scholar
• Sirisha, N.; Raghavachary, R. Efficient Synthesis of Dispiropyrrolidines Linked to Sugars. Int. J. Carbohydr. Chem. 2013, 2013, 1–7. DOI: 10.1155/2013/340546.
   Google Scholar
• Ghodsi, M. Z.; Razieh, M.; Negar, L. Synthesis of Spiro-Fused Heterocyclic Scaffolds Through Multicomponent Reactions Involving Isatin. Arkivoc 2016, 2016, 1–81. DOI: 10.3998/ark.5550190.p009.385.
   Web of Science ®Google Scholar
• Zhibin, H.; Qian, Z.; Gang, C. An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions. Molecules 2012, 17, 12704–12717. DOI: 10.3390/molecules171112704.
   PubMed Web of Science ®Google Scholar
• Ayyakannu, A.; Gangadhara, A.; Poonam, C. Synthesis of New Pyrimidine Derivatives via 1,3-Dipolar Cycloaddition and Their in-Silico Molecular Docking Studies as Thymidylate Synthase Inhibitors. Der Pharm. Lett. 2015, 7, 45–52.
   Google Scholar
• Anshu, D.; Ruby, S.; Shahnawaz, K.; Sukhbeer, K.; Pragya, S. 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
• Shvets, A. A.; Mikhailovskii, A. G.; Zimakov, D. V.; Kurbatov, S. V.; Surikova, O. V. New Ylidene Derivatives of Pyrrolo[2,1-α] Isoquinoline-2,3-Dione in the Synthesis of Dispiropyrrolidines. Russ. J. Org. Chem. 2011, 47, 1436–1438. DOI: 10.1134/S1070428011090314.
   Web of Science ®Google Scholar
• Gowri, S.; Gunasundari, T.; Raghunathan, R. A Greener Approach for the Synthesis of 1-N-Methyl-(Spiro [2.3′] Oxindolespiro [3.2″]/Spiro [2.3′] Indan-1,3-Dionespiro [2.2″]) Cyclopentanone-4-Arylpyrrolidines. Tetrahedron. Lett. 2007, 48, 319–322. DOI: 10.1016/j.tetlet.2006.11.002.
   Web of Science ®Google Scholar
• Raafat, M. Shaker,; Esam, A. I. Barbituric Acid Utility in Multi-Component Reactions. J. Chem. Sci. 2011, 66b, 1189–1201. DOI: 10.1515/znb-2011-1201.
   Google Scholar
• Ghodsi, M. Z.; Faezeh, A.; Negar, L. Recent Applications of Barbituric Acid in Multi-Component Reactions. RSC Adv. 2016, 6, 50895–50922. DOI: 10.1039/C6RA09874F.
   Web of Science ®Google Scholar
• Kesharwani, S.; Sahu, N. K.; Kohli, D. V. Synthesis and Biological Evaluation of Some New Spiro Derivatives of Barbituric Acid. Pharm. Chem. J. 2009, 43, 315–319. DOI: 10.1007/s11094-009-0298-8.
   Web of Science ®Google Scholar
• Hegde, S. G.; Koodlur, L.; Revanasiddappa, V. G.; Adimule, S. P.; Reddy, S. Y.; Ghoshal, A.; Nagabhushana, H. MgSiO3 NPs Catalyzed Intramolecular Cycloaddition Reaction: A Simple and Stereo Selective Synthesis of Unprecedented Julolidine Analogs. Syn. Commun. 2018, 48, 2485–2495. DOI: 10.1080/00397911.2018.1492725.
   Web of Science ®Google Scholar
• Hegde, S. G.; Hosamani, A.; Yellappa, S.; Vijayakumar, G. R.; Palakshamurthy, B. S. 5 -([1,1-Biphenyl]-4-yl)-1,1,3-Trimethyldispiro [Indane-2,2-Pyrrolidine-4,5-[1,3] Diazinane]-1,3,2,4,6-Pentaone. Acta. Cryst. Section E 2014, 70, 759. DOI: 10.1107/S1600536814013117.
   Google Scholar
• Sarojini, B. K.; Krishna, B. G.; Darshanraj, C. G.; Bharath, R. B.; Manjunatha, H. Synthesis, Characterization, in Vitro and Molecular Docking Studies of New 2,5-Dichloro Thienyl Substituted Thiazole Derivatives for Antimicrobial Properties. Eur. J. Med. Chem. 2010, 45, 3490–3496. DOI: 10.1016/j.ejmech.2010.03.039.
   PubMed Web of Science ®Google Scholar
• Kokura, S.; Yoshida, N.; Sakamoto, N.; Ishikawa, T.; Takagi, T.; Higashihara, H.; Nakabe, N.; Handa, O.; Naito, Y.; Yoshikawa, T. The Radical Scavenger Edaravone Enhances the anti-Tumor Effects of CPT-11 in Murine Colon Cancer by Increasing Apoptosis via Inhibition of NF-Kb. Cancer Lett. 2005, 229, 223–233. DOI: 10.1016/j.canlet.2005.06.039.
   PubMed Web of Science ®Google Scholar
• Francis, D.; Rita, L. Rapid Colorometric Assay for Cell Growth and Survival Modifications to the Tetrazolium Dye Procedure Giving Improved Sensitivity and Reliability. J. Immunol. Methods 1986, 89, 271–277. DOI: 10.1016/0022-1759(86)90368-6.
   PubMed Web of Science ®Google Scholar