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Research Articles

New One-Pot Pathway for the Synthesis of 2H–Pyrrolo[2,3-d]Pyrimidine-2,4-(3H)-Diones and 1H-Benzo[f]Indole-4,9-Dione Derivatives Substituted 3-Hydroxy-1,4-Naphthoquinonyl

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Pages 1602-1618 | Received 22 Sep 2021, Accepted 12 Jan 2022, Published online: 04 Feb 2022

References

  • Bryce A. Harrison, N. Andrew Whitlock, Michael V. Voronkov, Zheng Y. Almstead, Kun-jian Gu, Ross Mabon, Michael Gardyan, Brian D. Hamman, Jason Allen, Suma Gopinathan, et al., “Novel Class of LIM-Kinase 2 Inhibitors for the Treatment of Ocular Hypertension and Associated Glaucoma,” Journal of Medicinal Chemistry 52, no. 21 (2009): 6515–8.
  • Myung-Ho Jung, Hwan Kim, Won-Kyoung Choi, Mohammed I. El-Gamal, Jin-Hun Park, Kyung Ho Yoo, Tae Bo Sim, So Ha Lee, Daejin Baek, Jung-Mi Hah, et al., “Synthesis of Pyrrolo[2,3-d]Pyrimidine Derivatives and Their Antiproliferative Activity against Melanoma Cell Line,” Bioorganic & Medicinal Chemistry Letters 19, no. 23 (2009): 6538–43.
  • Y. Asukai, A. Valladares, C. Camps, E. Wood, K. Taipale, J. Arellano, A. Cassinello, J. A. Sacristán, and T. Dilla, “Cost-Effectiveness Analysis of Pemetrexed versus Docetaxel in the Second-Line Treatment of Non-Small Cell Lung Cancer in Spain: Results for the Non-Squamous Histology Population,” BMC Cancer 10 (2010): 26.
  • Tatiana McHardy, John J. Caldwell, Kwai-Ming Cheung, Lisa J. Hunter, Kevin Taylor, Martin Rowlands, Ruth Ruddle, Alan Henley, Alexis de Haven Brandon, Melanie Valenti, et al., “Discovery of 4-Amino-1-(7H-Pyrrolo[2,3-d]Pyrimidin-4-yl)Piperidine-4-Carboxamides as Selective, Orally Active Inhibitors of Protein Kinase B (Akt),” Journal of Medicinal Chemistry 53, no. 5 (2010): 2239–49.
  • A. Lauria, C. Patella, I. Abbate, A. Martorana, and A. M. Almerico, “Lead Optimization through VLAK Protocol: New Annelated Pyrrolo-Pyrimidine Derivatives as Antitumor Agents,” European Journal of Medicinal Chemistry 55 (2012): 375–83.
  • Ha-Soon Choi, Zhicheng Wang, Wendy Richmond, Xiaohui He, Kunyong Yang, Tao Jiang, Donald Karanewsky, Xiang-ju Gu, Vicki Zhou, Yi Liu, et al., “Design and Synthesis of 7H-Pyrrolo[2,3-d]Pyrimidines as Focal Adhesion Kinase Inhibitors. Part 2,” Bioorganic & Medicinal Chemistry Letters 16, no. 10 (2006): 2689–92.
  • S. M. Bennett, B. N. Nguyen, and K. K. Ogilvie, “Synthesis and Antiviral Activity of Some Acyclic and C-Acyclic Pyrrolo[2,3-d]Pyrimidine Nucleoside Analogues,” Journal of Medicinal Chemistry 33, no. 8 (1990): 2162–73.
  • C. Shih, V. J. Chen, L. S. Gossett, S. B. Gates, W. C. MacKellar, L. L. Habeck, K. A. Shackelford, L. G. Mendelsohn, D. J. Soose, V. F. Patel, et al., “LY231514, a Pyrrolo[2,3-d]Pyrimidine-Based Antifolate That Inhibits Multiple Folate-Requiring Enzymes,” Cancer Research 57 (1997): 1116–23.
  • Aleem Gangjee, Ojas A. Namjoshi, Jianming Yu, Michael A. Ihnat, Jessica E. Thorpe, and Linda A. Warnke, “Design, Synthesis and Biological Evaluation of Substituted Pyrrolo[2,3-d]Pyrimidines as Multiple Receptor Tyrosine Kinase Inhibitors and Antiangiogenic Agents,” Bioorganic & Medicinal Chemistry 16, no. 10 (2008): 5514–28.
  • B. A. Moharam, I. Jantan, J. Jalil, and F. Ahmad, “Inhibitory Effect of Compounds from Goniothalamus Tapis Miq. and Goniothalamus Uvaroides King on Platelet-Activating Factor Receptor Binding,” Phytotherapy Research : PTR 26, no. 5 (2012): 687–91.
  • C.-K. Ryu, J. Y. Lee, S. H. Jeong, and J.-H. Nho, “Synthesis and Antifungal Activity of 1H-Pyrrolo[3,2-g]Quinoline-4,9-Diones and 4,9-Dioxo-4,9-Dihydro-1H-Benzo[f]Indoles,” Bioorganic & Medicinal Chemistry Letters 19, no. 1 (2009): 146–8.
  • H. J. Park, H.-J. Lee, H.-Y. Min, H.-J. Chung, M. E. Suh, H.-Y. Park-Choo, C. Kim, H. J. Kim, E.-K. Seo, and S. K. Lee, “Inhibitory Effects of a Benz[f]Indole-4,9-Dione Analog on Cancer Cell Metastasis Mediated by the down-Regulation of Matrix Metalloproteinase Expression in Human HT1080 Fibrosarcoma Cells,” European Journal of Pharmacology 527, no. 1–3 (2005): 31–6.
  • E.-J. Lee, H.-J. Lee, H.-J. Park, H.-Y. Min, M.-E. Suh, H.-J. Chung, and S.-K. Lee, “Induction of G2/M Cell Cycle Arrest and Apoptosis by a Benz[f]Indole-4,9-Dione Analog in Cultured Human Lung (A549) Cancer Cells,” Bioorganic & Medicinal Chemistry Letters 14, no. 20 (2004): 5175–8.
  • H.-J. Lee, M.-E. Suh, and C.-O. Lee, “Synthesis and Cytotoxicity Evaluation of 2-Amino- and 2-Hydroxy-3-ethoxycarbonyl-N-Substituted-Benzo[f]Indole-4,9-Dione Derivatives,” Bioorganic & Medicinal Chemistry 11, no. 7 (2003): 1511–9.
  • Hyen Joo Park, Hyun-Jung Lee, Eun-Jin Lee, Hye Jin Hwang, Sang-Hee Shin, Myung-Eun Suh, Choonmi Kim, Hwa Jung Kim, Eun-Kyung Seo, and Sang Kook Lee, “Cytotoxicity and DNA Topoisomerase Inhibitory Activity of Benz[f]Indole-4,9-Dione Analogs,” Bioscience, Biotechnology and Biochemistry 67, no. 9 (2003): 1944–9.
  • J. D. Bauer, R. W. King, and S. F. Brady, “Utahmycins A and B, Azaquinones Produced by an Environmental DNA Clone,” Journal of Natural Products 73, no. 5 (2010): 976–9.
  • F. Nagai, K. Ushiyama, K. Satoh, and I. Kano, “DNA Cleavage by Phenylhydroquinone: The Major Metabolite of a Fungicide o-Phenylphenol,” Chemico-Biological Interactions 76, no. 2 (1990): 163–79.
  • M. Efdi, S. Fujita, T. Inuzuka, and M. Koketsu, “Chemical Studies on Goniothalamus Tapis Miq,” Natural Product Research 24, no. 7 (2010): 657–62.
  • C. J. Barnett, and L. M. Grubb, “Synthesis of Pyrrolo[2,3-d]Pyrimidines via Cyclocondensation of β-Alkoxy- and β-Amino-α-Bromoaldehydes,” Tetrahedron Letters 41, no. 50 (2000): 9741–5.
  • A. Davoodnia, M. Bakavoli, R. Moloudi, M. Khashi, and N. Tavakoli-Hoseini, “7-Deazapurines: Synthesis of New Pyrrolo[2,3-d]Pyrimidin-4-Ones Catalyzed by a Brønsted-Acidic Ionic Liquid as a Green and Reusable Catalyst,” Chinese Chemical Letters 21, no. 1 (2010): 1–4.
  • M. R. Mohammadizadeh, M. Bahramzadeh, and Z. Kh. Taghavi, “A Novel One-Pot and Efficient Procedure for the Synthesis of 3H-Spiro[Isobenzofuran-1,6′-Pyrrolo[2,3-d]Pyrimidine]-2′,3,4′,5′-Tetraones,” Tetrahedron Letters 51, no. 44 (2010): 5807–9.
  • S. Karamthulla, A. Jana, and L. H. Choudhury, “Synthesis of Novel 5,6-Disubstituted Pyrrolo [2,3-d]Pyrimidine-2,4-Diones via One-Pot Three-Component Reactions,” ACS Combinatorial Science 19, no. 2 (2017): 108–12.
  • M. Ahmadi Sabegh, J. Khalafy, and N. Etivand, “One-Pot, Three-Component Synthesis of a Series of New Bis-Pyrrolo[2,3-d]Pyrimidines in the Presence of TPAB under Reflux Conditions,” Journal of Heterocyclic Chemistry 55, no. 11 (2018): 2610–8.
  • A. Park, S. M. Choi, T. S. Kim, and E. K. Yum, “Microwave-Assisted Synthesis of 5,6,7-Trisubstituted Pyrrolo[2,3-d]Pyrimidines via Palladium-Catalyzed Heteroannulation with Internal Alkynes,” Bulletin of the Korean Chemical Society 40, no. 11 (2019): 1134–7.
  • X. Yang, C. Li, C. Qi, and F. Zhang, “Three-Component Reaction for Synthesis of 2-Amino-6-Aryl-5-(Phenylamino)-3,7-Dihydro-4H-Pyrrolo[2,3-d]Pyrimidin-4-One Derivatives in Water,” Journal of Heterocyclic Chemistry 57 (2020): 3271–8.
  • Jin-Wei Sun, Xiang-Shan Wang, and Yun Liu, “Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]Indole-4,9-Diones under Base-Free Condition,” The Journal of Organic Chemistry 78, no. 20 (2013): 10560–6.
  • Shanshan Guo, Binhui Chen, Xiao Guo, Guolin Zhang, and Yongping Yu, “Mn(II)-Catalyzed Synthesis of Benzo[f]Indole-4,9-Diones via Vinyl Azides and 2-Hydroxynaphthoquinone,” Tetrahedron 71, no. 49 (2015): 9371–5.
  • Y.-R. Chen, C.-H. Tseng, Y.-L. Chen, T.-L. Hwang, and C.-C. Tzeng, “Discovery of Benzo[f]Indole-4,9-Dione Derivatives as New Types of anti-Inflammatory Agents,” International Journal of Molecular Sciences 16, no. 3 (2015): 6532–44.
  • A. R. Nadji-Boukrouche, S. On, O. Khoumeri, T. Terme, and P. Vanelle, “Original Synthesis of Benzo[f]Indole-4,9-Dione Derivatives Using TDAE Strategy,” Tetrahedron Letters 56, no. 17 (2015): 2272–5.
  • L. Zhang, X. Zhang, Z. Lu, D. Zhang, and X. Xu, “Accessing Benzo[f]Indole-4,9-Diones via a Ring Expansion Strategy: silver-Catalyzed Tandem Reaction of Tosylmethyl Isocyanide (TosMIC) with 2-Methyleneindene-1,3-Diones,” Tetrahedron 72, no. 49 (2016): 7926–30.
  • T. Q. Nguyen, T. G. Le Nhat, D. Vu Ngoc, T. A. Dang Thi, H. T. Nguyen, P. H. Thi, H. H. Nguyen, H. T. Cao, K. A. Tehrani, and T. V. Nguyen, “Synthesis of Novel 2-Aryl-3-Benzoyl-1H-Benzo[f]Indole-4,9-Diones Using a Domino Reaction,” Tetrahedron Letters 57, no. 39 (2016): 4352–5.
  • Katarzyna Gach, Jakub Modranka, Jacek Szymański, Dorota Pomorska, Urszula Krajewska, Marek Mirowski, Tomasz Janecki, and Anna Janecka, “Anticancer Properties of New Synthetic Hybrid Molecules Combining Naphtho[2,3-b]Furan-4,9-Dione or Benzo[f]Indole-4,9-Dione Motif with Phosphonate Subunit,” European Journal of Medicinal Chemistry 120 (2016): 51–63.
  • M. S. Christodoulou, S. Giofre, E. M. Beccalli, F. Foschi, and G. Broggini, “Divergent Conversion of 4-Naphthoquinone-Substituted 4H-Isoxazolones to Different Benzo-Fused Indole Derivatives,” Organic Letters 22, no. 7 (2020): 2735–9.
  • R. Bharti, P. Kumari, T. Parvin, and L. H. Choudhury, “Molecular Diversity from the Three-Component Reaction of 2-Hydroxy-1,4-Naphthaquinone, Aldehydes and 6-Aminouracils: A Reaction Condition Dependent MCR,” RSC Advances 7, no. 7 (2017): 3928–33.
  • S. H. Mousavi, M. R. Mohammadizadeh, Z. Roshan, A. Jamaleddini, and S. Arimitsu, “One-Pot Synthesis of Spiro-Isobenzofuran Compounds via the Sequential Condensation/Oxidation Reaction of Ninhydrin with 4-Amino-1,2-Naphthoquinones/2-Amino-1,4-Naphthoquinones under Mild Conditions,” ACS Omega 5, no. 29 (2020): 18273–88.
  • S. Kumar, V. Kumar, and S. S. Chimni, “Novel Indium-Mediated Ternary Reactions between Indole-3-Carboxaldehydes–Allyl Bromide–Enamines: Facile Synthesis of Bisindolyl- and Indolyl-Heterocyclic Alkanes,” Tetrahedron Letters 44, no. 10 (2003): 2101–4.
  • Javad Azizian, Mohammad R. Mohammadizadeh, Ali A. Mohammadi, Ali R. Karimi, and Fatemeh Teimouri, “A Novel One-Pot Procedure for Preparation of Some New Condensed Pyrido[2,3-d]Pyrimidine(1H,3H)-2,4-Diones,” Heteroatom Chemistry 18, no. 1 (2007): 16–8.
  • J. Azizian, M. R. Mohammadizadeh, F. Teimouri, A. A. Mohammadi, and A. R. Karimi, “Reactions of 6‐Aminouracils: The First Simple, Fast, and Highly Efficient Synthesis of Bis(6‐Aminopyrimidonyl)Methanes (BAPMs) Using Thermal or Microwave‐Assisted Solvent‐Free Methods,” Synthetic Communications 36, no. 23 (2006): 3631–8.
  • R. Niess, and R. K. Robins, “A New Synthesis of the Pyrimido[4,5-d] Pyrimidine Ring. Preparation of Pyrimido[4,5-d] Pyrimidine-2,4,5,7-Tetrone,” Journal of Heterocyclic Chemistry 7, no. 1 (1970): 243–4.

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