Synthesis of Novel DPPH-Free Radical Scavenger Se-Containing Fused Chalcogenophenes: 2-Alkyl-7-Cyano-4-Imino-3-Phenyl-6-(pyrrolidin-1-yl)-3,4-Dihydroselenopheno[3,2-d]Pyrimidines

References

• S.S. Zade, N. Zamoshchik, and M. Bendikov, “Oligo‐and Polyselenophenes: A Theoretical Study,” Chemistry 15, no. 34 (2009): 8613–24.
   PubMed Web of Science ®Google Scholar
• A. Patra and M. Bendikov, “Polyselenophenes,” Journal of Materials Chemistry 20, no. 3 (2010): 422–33
   Web of Science ®Google Scholar
• R.S. Ashraf, I. Meager, M. Nikolka, M. Kirkus, M. Planells, B.C. Schroeder, S. Holliday, M. Hurhangee, C.B. Nielsen, H. Sirringhaus, et al, “Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells,” Journal of the American Chemical Society 137, no. 3 (2015): 1314–21.
   PubMed Web of Science ®Google Scholar
• G. Zeni, C.W. Nogueira, R.B. Panatieri, D.O. Silva, P.H. Menezes, A.L. Braga, C.C. Silveira, H.A. Stefani, and J.B. Rocha, “Synthesis and anti-Inflammatory Activity of Acetylenic Thiophenes,” Tetrahedron Letters 42, no. 45 (2001): 7921–3.
   Web of Science ®Google Scholar
• J.A. Wiles, A.S. Phadke, B.J. Bradbury, M.J. Pucci, J.A. Thanassi, and M. Deshpande, “Selenophene-Containing Inhibitors of Type IIA Bacterial Topoisomerases,” Journal of Medicinal Chemistry 54, no. 9 (2011): 3418–25.
   PubMed Web of Science ®Google Scholar
• H.S. Shiah, W.S. Lee, S.H. Juang, P.C. Hong, C.C. Lung, C.J. Chang, K.M. Chou, and J.Y. Chang, “Mitochondria-Mediated and p53-Associated Apoptosis Induced in Human Cancer Cells by a Novel Selenophene Derivative, D-501036,” Biochemical Pharmacology 73, no. 5 (2007): 610–9.
   PubMed Web of Science ®Google Scholar
• M.-J.R.P. Queiroz, R.C. Calhelha, L.A. Vale-Silva, E. Pinto, and M.S.-J. Nascimento, “Synthesis of Novel 3-(Aryl) Benzothieno [2, 3-c] Pyran-1-Ones from Sonogashira Products and Intramolecular Cyclization: Antitumoral Activity Evaluation,” European Journal of Medicinal Chemistry 44, no. 5 (2009): 1893–9.
   PubMed Web of Science ®Google Scholar
• E.A. Wilhelm, C.R. Jesse, C.F. Bortolatto, C.W. Nogueira, and L. Savegnago, “Antinociceptive and anti-Allodynic Effects of 3-Alkynyl Selenophene on Different Models of Nociception in Mice,” Pharmacology, Biochemistry, and Behavior 93, no. 4 (2009): 419–25.
   PubMed Web of Science ®Google Scholar
• S.W. May, L. Wang, M.M. Gill-Woznichak, R.F. Browner, A.A. Ogonowski, J.B. Smith, and S.H. Pollock, “An Orally Active Selenium-Based Antihypertensive Agent with Restricted CNS Permeability,” The Journal of Pharmacology and Experimental Therapeutics 283, no. 2 (1997): 470–7.
   PubMed Web of Science ®Google Scholar
• B. M. Gai, A. L. Stein, J. A. Roehrs, F. N. Bilheri, C. W. Nogueira, and G. Zeni, “Synthesis and Antidepressant-like Activity of Selenophenes Obtained via Iron (III)–PhSeSePh-Mediated Cyclization of Z-Selenoenynes,” Organic & Biomolecular Chemistry 10, no. 4 (2012): 798–807.
   PubMed Web of Science ®Google Scholar
• S.-H. Juang, C.-C. Lung, P.-C. Hsu, K.-S. Hsu, Y.-C. Li, P.-C. Hong, H.-S. Shiah, C.-C. Kuo, C.-W. Huang, Y.-C. Wang, et al, “D-501036, a Novel Selenophene-Based Triheterocycle Derivative, Exhibits Potent in Vitro and in Vivo Antitumoral Activity Which Involves DNA Damage and Ataxia Telangiectasia–Mutated Nuclear Protein Kinase Activation,” Molecular Cancer Therapeutics 6, no. 1 (2007): 193–202.
   PubMed Web of Science ®Google Scholar
• E.A. Wilhelm, B.M. Gai, A.C.G. Souza, C.F. Bortolatto, J.A. Roehrs, and C.W. Nogueira, “Involvement of GABAergic and Glutamatergic Systems in the Anticonvulsant Activity of 3-Alkynyl Selenophene in 21 Day-Old Rats,” Molecular and Cellular Biochemistry 365, no. 1–2 (2012): 175–80.
   PubMed Web of Science ®Google Scholar
• E.A. Wilhelm, C.R. Jesse, C.F. Bortolatto, C.W. Nogueira, and L. Savegnago, “Anticonvulsant and Antioxidant Effects of 3-Alkynyl Selenophene in 21-Day-Old Rats on Pilocarpine Model of Seizures,” Brain Research Bulletin 79, no. 5 (2009): 281–7.
   PubMed Web of Science ®Google Scholar
• R.F. Schumacher, A.R. Rosário, A.C. Souza, C.I. Acker, C.W. Nogueira, and G. Zeni, “The Potential Antioxidant Activity of 2, 3-Dihydroselenophene, a Prototype Drug of 4-Aryl-2, 3-Dihydroselenophenes,” Bioorganic & Medicinal Chemistry 19, no. 4 (2011): 1418–25.
   PubMed Web of Science ®Google Scholar
• F.C. Meotti, D.O. Silva, A.R. Dos Santos, G. Zeni, J.B.T. Rocha, and C.W. Nogueira, “Thiophenes and Furans Derivatives: A New Class of Potential Pharmacological Agents,” Environmental Toxicology and Pharmacology 15, no. 1 (2003): 37–44.
   PubMed Web of Science ®Google Scholar
• M. Erşatır, M. Yıldırım, E.S. Giray, and S. Yalın, “Synthesis and Antiproliferative Evaluation of Novel Biheterocycles Based on Coumarin and 2-Aminoselenophene-3-Carbonitrile Unit,” Monatshefte für Chemie [Chemical Monthly] 151, no. 4 (2020): 625–36.
   Google Scholar
• P.S. Hellwig, T.J. Peglow, F. Penteado, L. Bagnoli, G. Perin, and E.J. Lenardão, “Recent Advances in the Synthesis of Selenophenes and Their Derivatives,” Molecules 25, no. 24 (2020): 5907–010.
   PubMed Web of Science ®Google Scholar
• S. Umezawa, “Synthetische Versuche in der Selenophen-Gruppe. IV. Einführung von Seitenketten in den Selenophen-Kern,” Bulletin of the Chemical Society of Japan 14, no. 5 (1939): 155–61.
   Google Scholar
• C. Paal, “Ueber die Einwirkung von Phosphorpentaselenid auf das Acetonylaceton,” Berichte der deutschen chemischen Gesellschaft 18, no. 2 (1885): 2255–6.
   Google Scholar
• S. Kumar, H. Johansson, L. Engman, L. Valgimigli, R. Amorati, M.G. Fumo, and G.F. Pedulli, “Regenerable Chain-Breaking 2, 3-Dihydrobenzo [b] Selenophene-5-ol Antioxidants,” The Journal of Organic Chemistry 72, no. 7 (2007): 2583–95.
   PubMed Web of Science ®Google Scholar
• K.K. Casola, M.R. Gomes, D.F. Back, and G. Zeni, “Electrophilic Cyclization Involving Carbon–Selenium/Carbon–Halide Bond Formation: Synthesis of 3-Substituted Selenophenes,” The Journal of Organic Chemistry 83, no. 12 (2018): 6706–18.
   PubMed Web of Science ®Google Scholar
• R.F. Schumacher, A.R. Rosario, A.C.G. Souza, P.H. Menezes, and G. Zeni, “Synthesis of 2, 3-Dihydroselenophene and Selenophene Derivatives by Electrophilic Cyclization of Homopropargyl Selenides,” Organic Letters 12, no. 9 (2010): 1952–5.
   PubMed Web of Science ®Google Scholar
• R.F. Schumacher, A.R. Rosário, M.R. Leite, and G. Zeni, “Cyclization of Homopropargyl Chalcogenides by Copper (II) Salts: Selective Synthesis of 2, 3‐Dihydroselenophenes, 3‐Arylselenophenes, and 3‐Haloselenophenes/Thiophenes,” Chemistry 19, no. 39 (2013): 13059–64.
   PubMed Web of Science ®Google Scholar
• D.A. Barancelli, R.F. Schumacher, M.R. Leite, and G. Zeni, “Copper (II)‐Mediated Intramolecular Cyclization of (Z)‐Chalcogenoenynes: Synthesis of 3‐Halochalcogenophene Derivatives,” European Journal of Organic Chemistry 2011, no. 33 (2011): 6713–8.
   Web of Science ®Google Scholar
• V.A. D’yakonov, A.G. Ibragimov, L.M. Khalilov, A.A. Makarov, R.K. Timerkhanov, R.A. Tuktarova, O.A. Trapeznikova, and L.F. Galimova, “Dzhemilev Reaction in the Synthesis of Five-Membered Sulfur and Selenium Heterocycles,” Chemistry of Heterocyclic Compounds 45, no. 3 (2009): 317–26.
   Web of Science ®Google Scholar
• T.M. Klapötke, B. Krumm, and M. Scherr, “Halogenation of Dibenzoselenophene and Dibenzo [1, 2] Diselenine,” Zeitschrift für anorganische und allgemeine Chemie 636, no. 11 (2010): 1955–61.
   Web of Science ®Google Scholar
• B. Wu and N. Yoshikai, “Versatile Synthesis of Benzothiophenes and Benzoselenophenes by Rapid Assembly of Arylzinc Reagents, Alkynes, and Elemental Chalcogens,” Angewandte Chemie 52, no. 40 (2013): 10496–9.
   Google Scholar
• Z. Siroos, A. Hassanabadi, and M.H. Mosslemin, “Synthesis of Highly Functionalized Selenophenes via a Three-Component Condensation,” Phosphorus, Sulfur, and Silicon and the Related Elements 195, no. 10 (2020): 877–80.
   Web of Science ®Google Scholar
• Z. Siroos, A. Hassanabadi, and M.H. Mosslemin, “Three-Component Reaction between Dimethyl Acetylenedicarboxylate and 2-(3, 5-Dimethylpyrazole-1-Carbonyl)-3-Arylacrylonitrile in the Presence of Potassium Selenocyanate: A Synthesis of Highly Functionalized Selenophenes,” Polycyclic Aromatic Compounds 42, no. 2 (2022): 568–73.
   Web of Science ®Google Scholar
• S. Zhang, Q. Zhao, Y. Zhao, W. Yu, and J. Chang, “Synthesis of 2‐Amino Substituted Oxazoles from α‐Amino Ketones and Isothiocyanates via Sequential Addition and I2‐Mediated Desulfurative Cyclization,” Advanced Synthesis & Catalysis 362, no. 10 (2020): 1993–7.
   Web of Science ®Google Scholar
• M.K.A. Regal, S.S. Shaban, and S.A. El‐Metwally, “Facile Synthesis and Antimicrobial Activity of 5‐Amino‐3‐Methyl‐1‐Phenyl‐1 H‐Thieno [3, 2‐c] Pyrazole‐6‐Carbonitrile and Their Derivatives,” Journal of Heterocyclic Chemistry 56, no. 1 (2019): 226–33.
   Web of Science ®Google Scholar
• S. Jiao, Z. Wang, Q. Zhao, W. Yu, and J. Chang, “Synthesis of Fused 3-Amino-1, 2, 4-Triazoles via Sequential Addition of Aryl Hydrazines to Isothiocyanates and I2-Mediated Cyclodesulfurization,” Tetrahedron 74, no. 24 (2018): 3069–73.
   Web of Science ®Google Scholar
• M.M. Heravi and S. Moghimi, “An Efficient Synthesis of Thiazol-2-Imine Derivatives via a One-Pot, Three-Component Reaction,” Tetrahedron Letters. 53, no. 4 (2012): 392–4.
   Web of Science ®Google Scholar
• Q. Ding, X. He, and J. Wu, “Synthesis of 2-Aminobenzothiazole via Copper (I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate,” Journal of Combinatorial Chemistry 11, no. 4 (2009): 587–91.
   PubMedGoogle Scholar
• Q. Ding, B. Cao, X. Liu, Z. Zong, and Y.-Y. Peng, “Synthesis of 2-Aminobenzothiazole via FeCl3-Catalyzed Tandem Reaction of 2-Iodoaniline with Isothiocyanate in Water,” Green Chemistry 12, no. 9 (2010): 1607–10.
   Web of Science ®Google Scholar
• Y.-J. Guo, R.-Y. Tang, P. Zhong, and J.-H. Li, “Copper-Catalyzed Tandem Reactions of 2-Halobenzenamines with Isothiocyanates under Ligand-and Base-Free Conditions,” Tetrahedron Letters. 51, no. 4 (2010): 649–52.
   Web of Science ®Google Scholar
• N. Khatun, L. Jamir, M. Ganesh, and B.K. Patel, “A One-Pot Strategy for the Synthesis of 2-Aminobenzothiazole in Water by Copper Catalysis,” RSC Advances 2, no. 30 (2012): 11557–65.
   Web of Science ®Google Scholar
• P.S. Yadav, D. Devprakash, and G.P. Senthilkumar, “Benzothiazole: different Methods of Synthesis and Diverse Biological Activities,” ChemInform 42, no. 40 (2011).
   Google Scholar
• H.A. El‐Sayed and S.A. Said, “Direct Synthesis of Multi‐Functional Pyrimidine, Pyrazine, and Pyridine Scaffolds via Inter‐and Intramolecular Annulations of 3‐Amino‐Thieno [2, 3‐b] Pyridine‐2‐Carboxylate,” Journal of Heterocyclic Chemistry 56, no. 3 (2019): 1030–1037.
   Web of Science ®Google Scholar
• S. Sheikhi-Mohammareh, A. Shiri, H. Beyzaei, and E. Yarmohammadi, “New Efficient Design and Synthesis of Novel Antioxidant and Antifungal 7-Imino[1,3]Selenazolo[4,5-d]Pyrimidine-5(4H)-Thiones Utilizing a Base-Promoted Cascade Addition/Cyclization Sequence,” Monatshefte für Chemie – [Chemical Monthly] 151, no. 6 (2020): 963–969.
   Google Scholar
• S. Sheikhi-Mohammareh, A. Shiri, and M. Bakavoli, “Synthesis of New Derivatives of Pyrazolo [4, 3- e] [1, 2, 4] Triazolo [4, 3- c] Pyrimidine,” Journal of Chemical Research 39, no. 7 (2015): 403–406.
   Google Scholar
• S. Sheikhi-Mohammareh and A. Shiri, “An Alternative Regioselective Approach for the Synthesis of Highly Functionalized Derivatives of Pyrazolo[5,1- b] Purine Scaffold,” Journal of Heterocyclic Chemistry 55, no. 9 (2018): 2055–2060.
   Web of Science ®Google Scholar
• S. Bigonah-Rasti, S. Sheikhi-Mohammareh, K. Saadat, and A. Shiri, “Novel Tricyclic 2-Alkoxy-8-Methyl-6-(Pyrrolidin-1-yl)-4 H -[1,2,4]Triazolo[5,1- f] Purine Derivatives: Synthesis and Characterization,” Polycyclic Aromatic Compound 0 (2020): 1–11.
   Google Scholar
• S. Sheikhi‐Mohammareh, A. Shiri, E.H. Maleki, M.M. Matin, H. Beyzaei, P. Baranipour, F. Oroojalian, and T. Memariani, “Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]Pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents,” ChemistrySelect 5, no. 32 (2020): 10060–10066.
   Web of Science ®Google Scholar
• S. Sheikhi-Mohammareh, A. Shiri, and J. Mague, “Dimroth Rearrangement-Based Synthesis of Novel Derivatives of [1,3]Selenazolo[5,4-e][1,2,4]Triazolo[1,5-c]Pyrimidine as a New Class of Selenium-Containing Heterocyclic Architecture,” Molecular Diversity 26, no. 2 (2022): 923–937.
   PubMed Web of Science ®Google Scholar
• O. Kohandel, S. Sheikhi-Mohammareh, F. Oroojalian, T. Memariani, J. Mague, and A. Shiri, “A Dimroth Rearrangement Approach for the Synthesis of Selenopheno [2, 3-e][1, 2, 4] Triazolo [1, 5-c] Pyrimidines with Cytotoxic Activity on Breast Cancer Cells,” Molecular Diversity 26, no. 3 (2022): 1621–1633.
   PubMed Web of Science ®Google Scholar
• D. Thomae, E. Perspicace, D. Henryon, Z. Xu, S. Schneider, S. Hesse, G. Kirsch, and P. Seck, “One-Pot Synthesis of New Tetrasubstituted Thiophenes and Selenophenes,” Tetrahedron 65, no. 50 (2009): 10453–10458.
   Web of Science ®Google Scholar
• H. Beyzaei, M.K. Deljoo, R. Aryan, B. Ghasemi, M.M. Zahedi, and M. Moghaddam-Manesh, “Green Multicomponent Synthesis, Antimicrobial and Antioxidant Evaluation of Novel 5-Amino-Isoxazole-4-Carbonitriles,” Chemistry Central Journal 12, no. 1 (2018): 1–8.
   PubMedGoogle Scholar
• D.T. Ramadan, M.A.M. Ali, S.M. Yahya, and W.M. El-Sayed, “Correlation between Antioxidant/Antimutagenic and Antiproliferative Activity of Some Phytochemicals," Anti-Cancer Agents in Medicinal Chemistry 19, no. 12 (2019): 1481–1490.
   PubMed Web of Science ®Google Scholar
• K. Kleinrichert and B. Alappat, “Comparative Analysis of Antioxidant and anti-Amyloidogenic Properties of Various Polyphenol Rich Phytoceutical Extracts,” Antioxidants 8, no. 1 (2019): 13–11.
   Web of Science ®Google Scholar
• H. Dehghan, Y. Sarrafi, and P. Salehi, “Antioxidant and Antidiabetic Activities of 11 Herbal Plants from Hyrcania Region, Iran,” Journal of Food and Drug Analysis 24, no. 1 (2016): 179–188.
   PubMed Web of Science ®Google Scholar
• P. Diaz, S.C. Jeong, S. Lee, C. Khoo, and S.R. Koyyalamudi, “Antioxidant and anti-Inflammatory Activities of Selected Medicinal Plants and Fungi Containing Phenolic and Flavonoid Compounds,” Chinese Medicine 7, no. 1 (2012): 1–9.
   PubMedGoogle Scholar
• L.A. Tavadyan, Z.H. Manukyan, L.H. Harutyunyan, M.V. Musayelyan, A.D. Sahakyan, and H.G. Tonikyan, “Antioxidant Properties of Selenophene, Thiophene and Their Aminocarbonitrile Derivatives,” Antioxidants 6, no. 2 (2017): 22.
   Web of Science ®Google Scholar
• E.R. El-Sawy, H.M. Abo-Salem, M.S. Ebaid, A.E.-N. El-Gendy, and A.H. Mandour, “Synthesis and DPPH Radical-Scavenging Effect of Novel Heterocyclic Derivatives of 2-Amino-4-(1-Benzoylindol-3-yl) Selenophene-3-Carbonitrile,” Egyptian Pharmaceutical Journal 12, no. 2 (2013): 120–29.
   Google Scholar
• Y. Kotaiah, K. Nagaraju, N. Harikrishna, C.V. Rao, L. Yamini, and M. Vijjulatha, “Synthesis, Docking and Evaluation of Antioxidant and Antimicrobial Activities of Novel 1, 2, 4-Triazolo [3, 4-b][1, 3, 4] Thiadiazol-6-yl) Selenopheno [2, 3-d] Pyrimidines,” European Journal of Medicinal Chemistry 75 (2014): 195–202.
   PubMed Web of Science ®Google Scholar