Novel heteroannulated chromeno[3′,2′:5,6]pyrido[2,3-d]pyrido[2′,3′: 4,5][1,3]thiazolo[3,2-a]pyrimidines: synthesis, characterization and antimicrobial evaluation

References

• M. Fan, W. Yang, M. He, Y. Li, Z. Peng, and G. Wang, “Occurrence, Synthesis and Biological Activity of 2-(2-Phenyethyl)Chromones,” European Journal of Medicinal Chemistry 237 (2022): 114397.
   PubMed Web of Science ®Google Scholar
• S. Zhang, Y. Xie, L. Song, Y. Wang, H. Qiu, Y. Yang, C. Li, Z. Wang, Z. Han, and L. Yang, “Seven new 2-(2-Phenylethyl) Chromone Derivatives from Agarwood of Aquilaria agallocha with Inhibitory Effects on Nitric Oxide Production,” Fitoterapia 159 (2022): 105177.
   PubMed Web of Science ®Google Scholar
• P. Lerdsirisuk, C. Maicheen, and J. Ungwitayatorn, “Antimalarial Activity of HIV-1 Protease Inhibitor in Chromone Series,” Bioorganic Chemistry 57 (2014): 142–47. doi: 10.1016/j.bioorg.2014.10.006
   PubMed Web of Science ®Google Scholar
• T. E. Ali and M. A. Ibrahim, “Synthesis and Antimicrobial Activity of Chromone-linked 2-Pyridone Fused with 1,2,4-Triazoles, 1,2,4-Triazines and 1,2,4-Triazepines Ring Systems,” Journal of the Brazilian Chemical Society 21, no. 6 (2010): 1007–16. doi:10.1590/S0103-50532010000600010
   Web of Science ®Google Scholar
• Y. Liu, L. Ding, J. He, Z. Zhang, Y. Deng, S. He, and X. Yan, “A New Antibacterial Chromone from a Marine Sponge-associated Fungus Aspergillus sp. LS57,” Fitoterapia 154 (2021): 105004. doi:10.1016/j.fitote.2021.105004
   PubMed Web of Science ®Google Scholar
• O. Prakash, R. Kumar, and V. Parkash, “Synthesis and Antifungal Activity of Some New 3-Hydroxy-2-(1-Phenyl-3-Aryl-4-Pyrazolyl)Chromones,” European Journal of Medicinal Chemistry 43, no. 2 (2008): 435–40. doi:10.1016/j.ejmech.2007.04.004
   PubMed Web of Science ®Google Scholar
• V. M. Patil, N. Masand, S. Verma, and V. Masand, “Chromones: Privileged Scaffold in Anticancer Drug Discovery,” Chemical Biology & Drug Design 98, no. 5 (2021): 943–53. doi:10.1111/cbdd.13951
   PubMed Web of Science ®Google Scholar
• T. Zhou, Q. Shi, C.-H. Chen, H. Zhu, L. Huang, P. Ho, and K.-H. Lee, “Anti-AIDS Agents 79. Design, Synthesis, Molecular Modeling and Structure–Activity Relationships of Novel Dicamphanoyl-2′,2′-Dimethyldihydropyranochromone (DCP) Analogs as Potent anti-HIV Agents,” Bioorganic & Medicinal Chemistry 18, no. 18 (2010): 6678–89. doi:10.1016/j.bmc.2010.07.065
   PubMed Web of Science ®Google Scholar
• Y. Saito, Y. Taniguchi, S. Hirazawa, Y. Miura, H. Tsurimoto, T. Nakayoshi, A. Oda Hamel, K. Yamashita, M. Goto, et al, “Effects of Substituent Pattern on the Intracellular Target of Antiproliferative Benzo[b,]Thiophenyl Chromone Derivatives,” European Journal of Medicinal Chemistry 222 (2021): 113578.
   PubMed Web of Science ®Google Scholar
• A. Shanmugapriya, G. Kalaiarasi, M. Ravi, H. A. Sparkes, P. Kalaivani, and R. Prabhakaran, “Palladium-mediated C-O Bond Activation of Benzopyrone in 4-Oxo-4H-Chromene-3-Carbaldehyde-4(N)-Substituted Thiosemicarbazone: Synthesis, Structure, Nucleic Acid/Albumin Interaction, DNA Cleavage, Antioxidant and Cytotoxic Studies,” New Journal of Chemistry 45, no. 43 (2021): 20227–40. doi:10.1039/D1NJ04076F
   Web of Science ®Google Scholar
• Fang-Zheng Liu, Hao Wang, Wei Li, Li Yang, Jin-Ling Yang, Jing-Zhe Yuan, Yan-Mei Wei, Bei Jiang, Wen-Li Mei, and Hao-Fu Dai, “Filarones a and B, New Anti-inflammatory Dimeric 2-(2-Phenethyl) Chromones from Agarwood of Aquilaria filaria,” Phytochemistry Letters. 46 (2021): 11–14. doi:10.1016/j.phytol.2021.09.008
   Web of Science ®Google Scholar
• U. Albrecht, M. Lalk, and P. Langer, “Synthesis and Structure–Activity Relationships of 2-Vinylchroman-4-Ones as Potent Antibiotic Agents,” Bioorganic & Medicinal Chemistry 13, no. 5 (2005): 1531–36.
   PubMed Web of Science ®Google Scholar
• P.-L. Zhao, J. Li, and G. Fu, “Yang, Synthesis and Insecticidal Activity of Chromanone and Chromone Analogues of Diacylhydrazines,” Bioorganic & Medicinal Chemistry 15, no. 5 (2007): 1888–95.
   PubMed Web of Science ®Google Scholar
• G. F. Makhaeva, N. P. Boltneva, S. V. Lushchekina, E. V. Rudakova, O. G. Serebryakova, L. N. Kulikova, A. A. Beloglazkin, R. S. Borisov, and R. J. Richardson, “Synthesis, Molecular Docking, and Biological Activity of 2-Vinyl Chromones: Toward Selective Butyrylcholinesterase Inhibitors for Potential Alzheimer’s Disease Therapeutics,” Bioorganic & Medicinal Chemistry 26, no. 16 (2018): 4716–25.
   PubMed Web of Science ®Google Scholar
• M. A. Ibrahim, A. A. M. Farag, N. Roushdy, and N. M. El-Gohary, “Synthesis and Photosensitivity Characterizations of 9-(6-Bromo-4-Oxo-4H-Chromen-3-yl)-3,4,6,7-Tetrahydro-3,3,6,6-Tetramethyl-2H-Xanthene-1,8-(5H,9H)-Dione (BOCTTX),” Journal of Molecular Structure 1105 (2016): 370–80. doi:10.1016/j.molstruc.2015.10.060
   Web of Science ®Google Scholar
• A. A. M. Farag, N. Roushdy, S. Abdel Halim, N. M. El-Gohary, M. A. Ibrahim, and S. Said, “Synthesis, Molecular, Electronic Structure, Linear and Non-linear Optical and Phototransient Properties of 8-Methyl-1,2-Dihydro-4H-Chromeno[2,3-b]Quinoline-4,6(3H)-Dione (MDCQD): Experimental and DFT Investigations,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 191 (2018): 478–90. doi:10.1016/j.saa.2017.10.014
   PubMed Web of Science ®Google Scholar
• N. Tomer and R. Malhotra, “Schiff Base as a Fluorescent Sensor Derived from Chromone Moiety for the Effective Detection of Zn (II) Ions,” Journal of Molecular Structure 1252 (2022): 132124. doi:10.1016/j.molstruc.2021.132124
   Web of Science ®Google Scholar
• M. A. Ibrahim, “Ring Transformation of Chromone-3-Carboxamide,” Tetrahedron 65, no. 36 (2009): 7687–90. doi:10.1016/j.tet.2009.06.107
   Web of Science ®Google Scholar
• M. A. Ibrahim, “Studies on the Chemical Reactivity of 1H-Benzimidazol-2-Ylacetonitrile towards Some 3-Substituted Chromones: Synthesis of Some Novel Pyrido[1,2-a]Benzimidazoles,” Tetrahedron 69, no. 33 (2013): 6861–65. doi:10.1016/j.tet.2013.06.011
   Web of Science ®Google Scholar
• M. A. Ibrahim, “Ring Transformation of Chromone-3-Carboxamide under Nucleophilic Conditions,” Journal of the Brazilian Chemical Society 24 (2013): 1754–63.
   Web of Science ®Google Scholar
• M. A. Ibrahim and A. Badran, “Cascade Reactions between 2-Substituted-3-(4-Oxo-4H-Chromen-3-yl)Acrylonitriles with Benzylamine and p-Toluidine," ARKIVOC, vii (2018): 214–24.
   Google Scholar
• M. A. Ibrahim and A. M. El-Kazak, “Ring Opening and Recyclization Reactions with Chromone-3-Carbonitrile,” Journal of Heterocyclic Chemistry 56, no. 3 (2019): 1075–85. doi:10.1002/jhet.3495
   Web of Science ®Google Scholar
• M. A. Ibrahim, A. Badran, and S. H. Hashiem, “Heteroannulated Coumarins and Chromones from Chemical Transformations of 6,8‐Dimethylchromone‐3‐Carbonitrile,” Journal of Heterocyclic Chemistry 55, no. 12 (2018): 2844–51. doi:10.1002/jhet.3354
   Web of Science ®Google Scholar
• M. A. Ibrahim, N. M. El-Gohary, and S. Said, “Synthesis of Heteroannulated Chromeno[2,3-b]Pyridines: DBU Catalyzed Reactions of 2-Amino-6-Methylchromone-3-Carboxaldehyde with Some Heterocyclic Enols and Enamines,” Journal of Heterocyclic Chemistry 53, no. 1 (2016): 117–20. doi:10.1002/jhet.2285
   Web of Science ®Google Scholar
• M. A. Ibrahim, “Synthesis and Characterization of New Chromeno[2, 3-b]Pyridines via the Friedländer Reactions of 8-Allyl-2-Amino-4-Oxo-4H-Chromene-3-Carboxaldehyde,” European Journal of Chemistry 1, no. 2 (2010): 124–28. doi:10.5155/eurjchem.1.2.124-128.75.
   Google Scholar
• K. M. Elattar, R. Ramy, and M. M. Hammouda, “Recent Progress in the Chemistry of Bicyclic 6–6 Systems: Chemistry of Pyrido[1,2-a]Pyrimidines,” Monatshefte für Chemie - Chemical Monthly 148, no. 4 (2017): 601–27. doi:10.1007/s00706-016-1852-1
   Google Scholar
• K. M. Elattar, and B. D. Mert, “Recent Developments in the Chemistry of Bicyclic 6-6 Systems: Chemistry of Pyrido[4,3-d]Pyrimidines,” RSC Advances 6, no. 76 (2016): 71827–51. doi:10.1039/C6RA12364C
   Web of Science ®Google Scholar
• K. M. Elattar, R. Ramy, and M. M. Hammouda, “Recent Developments in the Chemistry of Bicyclic 6-6 Systems: Chemistry of Pyrido[1,2-c]Pyrimidines,” Synthetic Communications 46, no. 18 (2016): 1477–98. doi:10.1080/00397911.2016.1211702
   Google Scholar
• A. Nohara, T. Ishiguro, K. Ukawa, H. Sugihara, Y. Maki, and Y. Sanno, “Studies on Antianaphylactic Agents. 7. Synthesis of Antiallergic 5-Oxo-5H-[1]Benzopyrano[2,3-b]Pyridines,” Journal of Medicinal Chemistry 28, no. 5 (1985): 559–68. doi:10.1021/jm50001a005
   PubMed Web of Science ®Google Scholar
• M. I. Atta-Ur-Rahman, Choudhary  , and W. J. Thomsen, Bioassay Techniques for Drug Development (The Netherlands: Harwood Academic Publishers, 2001), 16.
   Google Scholar
• M. A. Ibrahim, S. A. Al-Harbi, and E. S. Allehyani, “Construction, Characterization, and Antimicrobial Evaluation of the Novel Heteroannulated Chromeno[2′′,3′′:6′,5′]Pyrido[2′,3′-d][1,3,]Thiazolo[3,2-a]Pyrimidines,” Journal of Heterocyclic Chemistry 58, no. 1 (2021): 241–49. doi:10.1002/jhet.4163
   Web of Science ®Google Scholar
• K. Hirota, Y. Kitade, H. Sajiki, and Y. Maki, “A Facile Synthesis of 7-Substituted Pyrimido[4,5-d]-Pyrimidine-2,4-Diones,” Communications 1984, no. 07 (1984): 589–90.
   Google Scholar
• S. S. Ibrahim, H. A. Allimony, A. M. Abdel-Halim, and M. A. Ibrahim, “Synthesis and Reactions of 8-Allylchromone-3-Carboxaldehyde,” Arkivoc 2009, no. 14 (2010): 28–38. doi:10.3998/ark.5550190.0010.e03
   Google Scholar
• Z. Hussain, M. A. Ibrahim, N. M. El-Gohary, and A. Badran, “Synthesis, Characterization, DFT, QSAR, Antimicrobial, and Antitumor Studies of Some Novel Pyridopyrimidines,” Journal of Molecular Structure 1269 (2022): 133870. doi:10.1016/j.molstruc.2022.133870
   Web of Science ®Google Scholar
• N. A. Alshaye and M. A. Ibrahim, “4-Amino-3-Formylcoumarin as Building Block for Construction of Novel Heteroannulated Coumarins: Synthesis, Characterization and Antimicrobial Evaluation,” Heterocycles 104, no. 12 (2022): 2179–94. doi:10.3987/COM-22-14748
   Google Scholar
• E. Abdel-Latif, A. S. Almatari, and G. E. Abd-ElGhani, “Synthesis and Antibacterial Evaluation of Some New Thiazole‐based Polyheterocyclic Ring Systems,” Journal of Heterocyclic Chemistry 56, no. 7 (2019): 1978–85. doi:10.1002/jhet.3577
   Web of Science ®Google Scholar
• M. S. Behalo, “Synthesis of Some Novel Thiazolo[3,2‐a]Pyrimidine and Pyrimido[2,1‐b][1,3]Thiazine Derivatives and their Antimicrobial Evaluation,” Journal of Heterocyclic Chemistry 55, no. 6 (2018): 1391–97. doi:10.1002/jhet.3174
   Web of Science ®Google Scholar
• S. K. Borthakur, P. K. Kalita, and S. Borthakur, “Synthesis and Antifungal Activities of 3,5‐Diphenyl‐7‐Amino[1,3]Thiazolo[3,2‐a]Pyrimidine‐6‐Nitrile Derivatives,” Journal of Heterocyclic Chemistry 57, no. 3 (2020): 1261–65. doi:10.1002/jhet.3863
   Web of Science ®Google Scholar