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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 3
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Articles

A facile method for preparation and evaluation of the antimicrobial efficiency of various heterocycles containing thieno[2,3-d]pyrimidine

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Pages 398-409 | Received 15 Jul 2020, Published online: 23 Oct 2020

References

  • Adepu, R.; Rambabu, D.; Prasad, B.; Meda, C. L. T.; Kandale, A.; Rama Krishna, G.; Malla Reddy, C.; Chennuru, L. N.; Parsa, K. V. L.; Pal, M. Novel Thieno[2,3-d]Pyrimidines: Their Design, Synthesis, Crystal Structure Analysis and Pharmacological Evaluation. Org. Biomol. Chem. 2012, 10, 5554–5569. DOI: 10.1039/c2ob25420d.
  • Abdallah, M. A.; Naturforsch, Z. A Facile One-Pot Synthesis of 1,4,7,8,9,10-Hexahydro-6H-[1]- Benzothieno[2′,3′:4,5]Pyrimido[1,2-b][1,2,4,5]Tetrazin-6-Ones. Verlag. Der Zeitschrift. Für. Naturforschung. 2002, 57b, 699–706.
  • El-Gazzar, A. B. A.; Hussein, H. A. R.; Hafez, H. N. Synthesis and Biological Evaluation of Thieno[2,3-d]Pyrimidine Derivatives for Anti-Inflammatory, Analgesic and Ulcerogenic Activity. Acta Pharm. 2007, 57, 395–411. DOI: 10.2478/v10007-007-0032-6.
  • Hozien, Z. A.; Atta, F. M.; Hassan, K. M.; Abdel-Wahab, A. A.; Ahmed, S. A. Synthesis and Application of Some New Tienopyrimidine Derivatives as Antimicrobial Agents. Synth. Commun. 1996, 26, 3733–3755. DOI: 10.1080/00397919608003791.
  • Hill, P. J.; Abibi, A.; Albert, R.; Andrews, B.; Gagnon, M. M.; Gao, N.; Grebe, T.; Hajec, L. I.; Huang, J.; Livchak, S.; et al. Selective Inhibitors of Bacterial t-RNA-(N(1)G37) Methyltransferase (TrmD) That Demonstrate Novel Ordering of the Lid Domain. J. Med. Chem. 2013, 56, 7278–7288. DOI: 10.1021/jm400718n.
  • Kanawade, S. B.; Toche, R. B.; Rajani, D. P. Synthetic Tactics of New Class of 4-Aminothieno[2,3-d]Pyrimidine-6-Carbonitrile Derivatives Acting as Antimicrobial Agents. Eur. J. Med. Chem. 2013, 64, 314–320. DOI: 10.1016/j.ejmech.2013.03.039.
  • Tani, N.; Rahnasto-Rilla, M.; Wittekindt, C.; Salminen, K. A.; Ritvanen, A.; Ollakka, R.; Koskiranta, J.; Raunio, H.; Juvonen, R. O. Antifungal Activities of Novel Non-Azole Molecules against S. cerevisiae and C. albicans. Eur. J. Med. Chem. 2012, 47, 270–277. DOI: 10.1016/j.ejmech.2011.10.053.
  • De, J. S.; Gao, L.-J.; Herdewijn, P.; Herman, J.; Jang, M.; Leyssen, P.; Louat, T.; Neyts, J.; Pannecouque, C.; Vanderhoydonck, B. WO Patent Appl. 2011147753.
  • Leung, C. Y.; Langille, A. M.; Mancuso, J.; Tsantrizos, Y. S. Discovery of Thienopyrimidine-Based Inhibitors of the Human Farnesyl Pyrophosphate Synthase–Parallel Synthesis of Analogs via a Trimethylsilyl Ylidene Intermediate. Bioorg. Med. Chem. 2013, 21, 2229–2240. DOI: 10.1016/j.bmc.2013.02.006.
  • Leung, C. Y.; Park, J.; De Schutter, J. W.; Sebag, M.; Berghuis, A. M.; Tsantrizos, Y. S. Thienopyrimidine Bisphosphonate (ThPBP) Inhibitors of the Human Farnesyl Pyrophosphate Synthase: Optimization and Characterization of the Mode of Inhibition. J. Med. Chem. 2013, 56, 7939–7990. DOI: 10.1021/jm400946f.
  • Jang, M. Y.; De Jonghe, S.; Van Belle, K.; Louat, T.; Waer, M.; Herdewijn, P. Synthesis, Immunosuppressive Activity and Structure-Activity Relationship Study of a New Series of 4-N-Piperazinyl-Thieno[2,3-d]Pyrimidine Analogues. Bioorg. Med. Chem. Lett. 2010, 20, 844–847. DOI: 10.1016/j.bmcl.2009.12.098.
  • Tintori, C.; Laurenzana, I.; La Rocca, F.; Falchi, F.; Carraro, F.; Ruiz, A.; Este, J. A.; Kissova, M.; Crespan, E.; Maga, G.; et al. Identification of Hck Inhibitors as Hits for the Development of Antileukemia and Anti-HIV Agents. ChemMedChem. 2013, 8, 1353–1361. DOI: 10.1002/cmdc.201300204.
  • Shook, B. C.; Chakravarty, D.; Barbay, J. K.; Wang, A.; Leonard, K.; Alford, V.; Powell, M. T.; Rassnick, S.; Scannevin, R. H.; Carroll, K.; et al. Substituted Thieno[2,3-d]Pyrimidines as Adenosine A2A Receptor Antagonists. Bioorg. Med. Chem. Lett. 2013, 23, 2688–2691. DOI: 10.1016/j.bmcl.2013.02.078.
  • Barbay, J. K.; Chakravarty, D.; Shook, B. C.; Wang, A. Preparation of methylene amines of thieno[2,3‐d]pyrimidine and their use as adenosine A2A receptor antagonists. WO Patent Appl. 2010045006.
  • Wood, E. R.; Shewchuk, L. M.; Ellis, B.; Brignola, P.; Brashear, R. L.; Caferro, T. R.; Dickerson, S. H.; Dickson, H. D.; Donaldson, K. H.; Gaul, M.; et al. [ 6-Ethynylthieno[3,2-d]- and 6-Ethynylthieno[2,3-d]Pyrimidin-4-Anilines as Tunable Covalent Modifiers of ErbB Kinases. Proc. Natl. Acad. Sci. USA. 2008, 105, 2773–2778. DOI: 10.1073/pnas.0708281105.
  • Dai, Y.; Guo, Y.; Frey, R. R.; Ji, Z.; Curtin, M. L.; Ahmed, A. A.; Albert, D. H.; Arnold, L.; Arries, S. S.; Barlozzari, T.; et al. Thienopyrimidine Ureas as Novel and Potent Multitargeted Receptor Tyrosine Kinase Inhibitors. J. Med. Chem. 2005, 48, 6066–6083. DOI: 10.1021/jm050458h.
  • Hsieh, H. P.; Coumar, S. M.; Hsu, T. A.; Lin, W. H.; Chen, Y. R.; Chao, Y. S. Fused bicyclic and tricyclic pyrimidine compounds as tyrosine kinase inhibitors. US Patent Appl. 20100120805.
  • Wu, C. H.; Coumar, M. S.; Chu, C. Y.; Lin, W. H.; Chen, Y. R.; Chen, C. T.; Shiao, H. Y.; Rafi, S.; Wang, S. Y.; Hsu, H.; et al. Design and Synthesis of Tetrahydropyridothieno[2,3-d]Pyrimidine Scaffold Based Epidermal Growth Factor Receptor (EGFR) Kinase Inhibitors: The Role of Side Chain Chirality and Michael Acceptor Group for Maximal Potency. J. Med. Chem. 2010, 53, 7316–7326. DOI: 10.1021/jm100607r.
  • Zhao, A.; Gao, X.; Wang, Y.; Ai, J.; Wang, Y.; Chen, Y.; Geng, M.; Zhang, A. Discovery of Novel c-Met Kinase Inhibitors Bearing a Thieno 2,3-d]Pyrimidine or Furo[2,3-d]Pyrimidine Scaffold. Bioorg. Med. Chem. 2011, 19, 3906–3918. DOI: 10.1016/j.bmc.2011.05.038.
  • Zhang, J. CN Patent Appl. 102872018.
  • Heffron, T. P.; Wei, B. Q.; Olivero, A.; Staben, S. T.; Tsui, V.; Do, S.; Dotson, J.; Folkes, A. J.; Goldsmith, P.; Goldsmith, R.; et al. Rational Design of Phosphoinositide 3-Kinase α Inhibitors That Exhibit Selectivity over the Phosphoinositide 3-Kinase β Isoform. J. Med. Chem. 2011, 54, 7815–7833. DOI: 10.1021/jm2007084.
  • Bugge, S.; Kaspersen, S. J.; Larsen, S.; Nonstad, U.; Bjørkøy, G.; Sundby, E.; Hoff, B. H. Structure-Activity Study Leading to Identification of a Highly Active Thienopyrimidine Based EGFR Inhibitor. Eur. J. Med. Chem. 2014, 75, 354–374. DOI: 10.1016/j.ejmech.2014.01.042.
  • Aponte, J. C.; Vaisberg, A. J.; Castillo, D.; Gonzalez, G.; Estevez, Y.; Arevalo, J.; Quiliano, M.; Zimic, M.; Verástegui, M.; Málaga, E.; et al. Trypanoside, Anti-Tuberculosis, Leishmanicidal, and Cytotoxic Activities of Tetrahydrobenzothienopyrimidines. Bioorg. Med. Chem. 2010, 18, 2880–2886. DOI: 10.1016/j.bmc.2010.03.018.
  • Habib, N. S.; Soliman, R.; El-Tombary, A. A.; El-Hawash, S. A.; Shaaban, O. G. Synthesis and Biological Evaluation of Novel Series of Thieno[2,3-d]Pyrimidine Derivatives as Anticancer and Antimicrobial Agents. Med. Chem. Res. 2013, 22, 3289–3308. DOI: 10.1007/s00044-012-0324-3.
  • Cai, B. Q.; Jin, H. X.; Yan, X. J.; Zhu, P.; Hu, G. X. 3D-QSAR and 3D-QSSR Studies of Thieno[2,3-d]Pyrimidin-4-yl Hydrazone Analogues as CDK4 Inhibitors by CoMFA Analysis. Acta Pharmacol. Sin. 2014, 35, 151–160. DOI: 10.1038/aps.2013.105.
  • Kjær, S.; Linch, M.; Purkiss, A.; Kostelecky, B.; Knowles, P. P.; Rosse, C.; Riou, P.; Soudy, C.; Kaye, S.; Patel, B.; et al. Adenosine-Binding Motif Mimicry and Cellular Effects of a Thieno[2,3-d]Pyrimidine-Based Chemical Inhibitor of Atypical Protein Kinase C Isoenzymes. Biochem. J. 2013, 451, 329–342. DOI: 10.1042/BJ20121871.
  • Horiuchi, T.; Takeda, Y.; Haginoya, N.; Miyazaki, M.; Nagata, M.; Kitagawa, M.; Akahane, K.; Uoto, K. Discovery of Novel Thieno[2,3-d]Pyrimidin-4-yl Hydrazone-Based Cyclin-Dependent Kinase 4 Inhibitors: synthesis, Biological Evaluation and Structure-Activity Relationships. Chem. Pharm. Bull. 2011, 59, 991–1002. DOI: 10.1248/cpb.59.991.
  • Horiuchi, T.; Nagata, M.; Kitagawa, M.; Akahane, K.; Uoto, K. Discovery of Novel Thieno[2,3-d]Pyrimidin-4-yl Hydrazone-Based Inhibitors of Cyclin D1-CDK4: synthesis, Biological Evaluation and Structure-Activity Relationships. Part 2. Bioorg. Med. Chem. 2009, 17, 7850–7860. DOI: 10.1016/j.bmc.2009.10.039.
  • McClellan, W. J.; Dai, Y.; Abad-Zapatero, C.; Albert, D. H.; Bouska, J. J.; Glaser, K. B.; Magoc, T. J.; Marcotte, P. A.; Osterling, D. J.; Stewart, K. D.; et al. Discovery of Potent and Selective Thienopyrimidine Inhibitors of Aurora Kinases. Bioorg. Med. Chem. Lett. 2011, 21, 5620–5624. DOI: 10.1016/j.bmcl.2011.06.041.
  • Gangjee, A.; Li, W.; Kisliuk, R. L.; Cody, V.; Pace, J.; Piraino, J.; Makin, J. Design, Synthesis, and X-Ray Crystal Structure of Classical and Nonclassical 2-Amino-4-Oxo-5-Substituted-6-Ethylthieno[2,3-d]Pyrimidines as Dual Thymidylate Synthase and Dihydrofolate Reductase Inhibitors and as Potential Antitumor Agents. J. Med. Chem. 2009, 52, 4892–4902. DOI: 10.1021/jm900490a.
  • Gangjee, A.; Qiu, Y.; Li, W.; Kisliuk, R. L. Potent Dual Thymidylate Synthase and Dihydrofolate Reductase Inhibitors: Classical and Nonclassical 2-Amino-4-Oxo-5-Arylthio-Substituted-6-Methylthieno[2,3-d]Pyrimidine Antifolates. J. Med. Chem. 2008, 51, 5789–5797. DOI: 10.1021/jm8006933.
  • Gangjee, A.; Qiu, Y.; Kisliuk, R. L. Synthesis of Classical and Nonclassical 2‐Amino‐4‐Oxo‐6‐Benzylthieno‐[2,3‐d]Pyrimidines as Potential Thymidylate Synthase Inhibitors. J. Heterocycl. Chem. 2004, 41, 941–946. DOI: 10.1002/jhet.5570410613.
  • Ni, Y.; Gopalsamy, A.; Cole, D.; Hu, Y.; Denny, R.; Ipek, M.; Liu, J.; Lee, J.; Hall, J. P.; Luong, M.; et al. Identification and SAR of a New Series of Thieno[3,2-d]Pyrimidines as Tpl2 Kinase Inhibitors. Bioorg. Med. Chem. Lett. 2011, 21, 5952–5956. DOI: 10.1016/j.bmcl.2011.07.069.
  • Heffron, T. P.; Berry, M.; Castanedo, G.; Chang, C.; Chuckowree, I.; Dotson, J.; Folkes, A.; Gunzner, J.; Lesnick, J. D.; Lewis, C.; et al. Identification of GNE-477, a Potent and Efficacious Dual PI3K/mTOR Inhibitor. Bioorg. Med. Chem. Lett. 2010, 20, 2408–2411. DOI: 10.1016/j.bmcl.2010.03.046.
  • Sutherlin, D. P.; Sampath, D.; Berry, M.; Castanedo, G.; Chang, Z.; Chuckowree, I.; Dotson, J.; Folkes, A.; Friedman, L.; Goldsmith, R.; et al. Discovery of (Thienopyrimidin-2-yl)Aminopyrimidines as Potent, Selective, and Orally Available pan-PI3-Kinase and Dual pan-PI3-Kinase/mTOR Inhibitors for the Treatment of Cancer. J. Med. Chem. 2010, 53, 1086–1097. DOI: 10.1021/jm901284w.
  • Kamal El-Dean, A. M.; Zaki, R. M.; Abdulrazzaq, A. Y. A Convenient Synthesis and Biological Activity of Novel Thieno[2,3-c]Pyrazole Compounds as Antimicrobial and Anti-Inflammatory Agents. Russ. J. Bioorg. Chem. 2015, 41, 97–104. DOI: 10.1134/S1068162015010057.
  • Saddik, A. A.; Kamal El-Dean, A. M.; El-Said, W. A.; Hassan, K. M.; Abbady, M. S. Synthesis, Antimicrobial, and Anticancer Activities of a New Series of Thieno[2,3-d] Pyrimidine Derivatives. J. Heterocyclic Chem. 2018, 55, 2111–2122. DOI: 10.1002/jhet.3256.
  • Kamal El Dean, A. M.; Zaki, R. M.; Geies, A. A.; Radwan, S. M.; Tolba, M. S. Synthesis and Antimicrobial Activity of New Heterocyclic Compounds Containing Thieno[3,2-C]Coumarin and Pyrazolo[4,3-C]Coumarin Frameworks. Russ. J. Bioorganic Chem. 2013, 39, 619–630.
  • Zaki, R. M.; Radwan, S. M.; Kamal El Dean, A. M. Synthesis and Reactions of 1-Amino-5-Morpholin-4-yl-6,7,8,9-Tetrahydrothieno[2,3-c]Isoquinoline. J. Chin. Chem. Soc. 2011, 58, 544–554. DOI: 10.1002/jccs.201190019.
  • Zaki, R. M.; Kamal El Dean, A. M.; Radwan, S. M.; Abd Ul-Malik, M. A. A Convenient Synthesis, Reactions and Biological Activities of Some Novel Thieno[3,2-e]Pyrazolo[3,4-b]Pyrazine Compounds as Anti-Microbial and Antiinflammatory Agents. Curr. Organic Synth. 2018, 15, 863–871. DOI: 10.2174/1570179415666180607105627.
  • Kamal El Dean, A. M.; Radwan, S. M.; Zaki, R. M. Synthesis of Morphlinotetrahydrothieno [2, 3‐c] Isoquinolines. J. Chin. Chem. Soc. 2008, 55, 1290–1299. DOI: 10.1002/jccs.200800193.
  • Zaki, R. M.; Kamal El Dean, A. M.; Abd El Monem, M. I.; Seddik, M. A. Novel Synthesis and Reactions of Pyrazolyl-Substituted Tetrahydrothieno [2,3-c] Isoquinoline Derivatives. Heterocycl. Commun. 2016, 22, 103–109. DOI: 10.1515/hc-2015-0204.
  • Kamal, A. M.; Radwan, S. M.; Zaki, R. M. Synthesis and Biological Activity of Pyrazolothienotetrahydroisoquinoline and [1,2,4]Triazolo[3,4-a]Thienotetrahydro-Isoquinoline Derivatives. Eur. J. Med. Chem. 2011, 46, 567–578. DOI: 10.1016/j.ejmech.2010.11.036.
  • Sayed, M.; Kamal El-Dean, A. M.; Ahmed, M.; Hassanien, R. Synthesis of Some Heterocyclic Compounds Derived from Indole as Antimicrobial Agents. Synth. Commun. 2018, 48, 413–421. DOI: 10.1080/00397911.2017.1403627.
  • Tolba, M. S.; Kamal El-Dean, A. M.; Ahmed, M.; Hassanien, R.; Farouk, M. Synthesis and Antimicrobial Activity of Some New Thienopyrimidine Derivatives. ARKIVOC 2017, 5, 229–243.
  • Tolba, M. S.; Ahmed, M.; Kamal El-Dean, A. M.; Hassanien, R.; Farouk, M. Synthesis of New Fused Thienopyrimidines Derivatives as Anti‐Inflammatory Agents. J. Heterocyclic Chem. 2018, 55, 408–418. DOI: 10.1002/jhet.3056.
  • Sayed, M.; Younis, O.; Hassanien, R.; Ahmed, M.; Mohammed, A. A. K.; Kamal, A. M.; Tsutsumi, O. Design and Synthesis of Novel Indole Derivatives with Aggregation-Induced Emission and Antimicrobial Activity. J. Photochem. Photobiol. A. 2019, 383, 111969–111979. DOI: 10.1016/j.jphotochem.2019.111969.
  • Younis, O.; Tolba, M. S.; Orabi, E. A.; Kamal, A. M.; Hassanien, R.; Tsutsumi, O.; Ahmed, M. Biologically-Active Heterocyclic Molecules with Aggregation-Induced Blue-Shifted Emission and Efficient Luminescence Both in Solution and Solid States. J. Photochem. Photobiol. A. 2020, 400, 112642. DOI: 10.1016/j.jphotochem.2020.112642.
  • Kamal El-Dean, A. M.; Zaki, R. M.; Radwan, S. M.; Saber, A. F. Synthesis, Reactions and Spectral Characterization of Novel Thienopyrazole Derivatives. Eur. Chem. Bull. 2017, 6, 550–553.
  • Zaki, R. M.; Kamal El-Dean, A. M.; Radwan, S. M.; Saber, A. F. Efficient Synthesis, Reactions and Spectral Characterization of Novel Pyrazolo[4',3':4,5]Thieno[3,2-d]Pyrimidin Derivatives and Their Related Heterocycles. Heterocycl. Commun. 2019, 25, 39–46. DOI: 10.1515/hc-2019-0004.
  • Saber, A. F.; Zaki, R. M.; Kamal El-Dean, A. M.; Radwan, S. M. Synthesis, Reactions and Spectral Characterization of Some New Biologically Active Compounds Derived from Thieno[2,3-c]Pyrazole-5-Carboxamide. J. Heterocyclic Chem. 2020, 57, 238–247. DOI: 10.1002/jhet.3769.
  • Tolba, M. S.; Kamal El-Dean, A. M.; Ahmed, M.; Hassanien, R. Synthesis, Reactions, and Biological Study of Some New Thienopyrimidine Derivatives as Antimicrobial and anti-Inflammatory Agents. J. Chin. Chem. Soc. 2019, 66, 548–557. DOI: 10.1002/jccs.201800292.
  • Kwon-Chung, K. J.; Bennett, J. E. Principles of Anti-Fungal Therapy Superficial Mycoses. In Medical Mycology; KwonChung, K. J.; Bennett, J. E., Eds.; Lea & Febiger: Philadelphia, PA, 1992; pp 81–102.

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