Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 54, 2024 - Issue 10
65
Views
0
CrossRef citations to date
0
Altmetric
Articles

Novel annulated chromeno[3',2':5,6]pyrido[2,3-d][1,3,4]thiadiazolo[3,2-a] pyrimidines and chromeno[3'',2'':5',6']pyrido[2',3':4,5]pyrimido[2,1-b][1,3,4] thiadiazines: Synthetic approaches and antimicrobial efficiency

, , , &
Pages 843-852 | Received 10 Feb 2024, Published online: 01 May 2024

References

  • Dey, S.; Bajaj, S. O. Promising Anticancer Drug Thapsigargin: A Perspective toward the Total Synthesis. Synth. Commun. 2018, 48, 1–13. DOI: 10.1080/00397911.2017.1386789.
  • Kirishnamaline, G.; Magdaline, J. D.; Chithambarathanu, T. Structural Elucidation, Spectroscopic Investigation, in Silico Docking, and in Vitro Cytotoxicity Studies of Chromone Derivatives as Potential anti-Breast Cancer Agents. J. Mol. Struct. 2023, 1284, 135306. DOI: 10.1016/j.bmcl.2022.128799.
  • Xing, T.; Yu, S.; Qin, M.; Zhang, M.; Ma, Y.; Xiao, Z. Synthesis, anti-Inflammatory Activity, and Conformational Relationship Studies of Chromone Derivatives Incorporating Amide Groups. Bioorg. Med. Chem. Lett. 2023, 96, 129539. DOI: 10.1016/j.bmcl.2023.129539.
  • Fu, Y.-H.; Guo, J.-M.; Xie, Y.-T.; Yu, X.-M.; Su, Q.-T.; Qiang, L.; Kong, L.-Y.; Liu, Y.-P. Prenylated Chromones from the Fruits of Artocarpus Heterophyllus and Their Potential anti-HIV-1 Activities. J. Agric. Food Chem. 2020, 68, 2024–2030. DOI: 10.1021/acs.jafc.9b06417.
  • Boya, B. R.; Lee, J.-H.; Lee, J. Antimicrobial and Antibiofilm Activities of Chromone Derivatives against Uropathogenic Escherichia coli. Microbiol. Res. 2024, 278, 127537. DOI: 10.1016/j.micres.2023.127537.
  • T. N. , M. M.; K. , S.; Asiri, A. M.; Sobahi, T. R.; Asad, M. Green Synthesis of Chromonyl Chalcone and Pyrazoline as Potential Antimicrobial Agents– DFT, Molecular Docking and Antimicrobial Studies. J. Mol. Struct. 2023, 1271, 133993. DOI: 10.1016/j.molstruc.2022.133993.
  • Maicheen, C.; Ungwitayatorn, J. Antimalarial and β-Hematin Formation Inhibitory Activities of Chromone Derivatives. Sci. Asia 2019, 45, 221–228. DOI: 10.2306/scienceasia1513-1874.2019.45.221.
  • Al-Majedy, Y. K.; Ibraheem, H. H.; Issa, A. A.; Jabir, M. S.; Hasoon, B. A.; Al-Shmgani, H. S.; Sulaiman, G. M. Synthesis, Biomedical Activities, and Molecular Docking Study of Novel Chromone Derivatives. J. Mol. Struct. 2024, 1295, 136647. DOI: 10.1016/j.molstruc.2023.136647.
  • Fan, M.; Yang, W.; Liu, L.; Peng, Z.; He, Y.; Wang, G. Design, Synthesis, Biological Evaluation, and Docking Study of Chromone-Based Phenylhydrazone and Benzoylhydrazone Derivatives as Antidiabetic Agents Targeting α-Glucosidase, Bioorg. Bioorg. Chem. 2023, 132, 106384. DOI: 10.1016/j.bioorg.2023.106384.
  • Zhang, C.; Zhang, Y.; Lv, Y.; Guo, J.; Gao, B.; Lu, Y.; Zang, A.; Zhu, X.; Zhou, T.; Xie, Y. Chromone-Based Monoamine Oxidase B Inhibitor with Potential Iron-Chelating Activity for the Treatment of Alzheimer’s Disease. J. Enzyme Inhib. Med. Chem. 2023, 38, 100–117. DOI: 10.1080/14756366.2022.2134358.
  • Farag, A. A. M.; Roushdy, N.; Abdel Halim, S.; El-Gohary, N. M.; Ibrahim, M. A.; Said, S. 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, Spectrochim. Spectrochim. Acta. A Mol. Biomol. Spectrosc. 2018, 191, 478–490. DOI: 10.1016/j.saa.2017.10.014.
  • Abozeid, M. A.; El-Kholany, M. R.; Abouzeid, L. A.; Abdel-Rahman, A. H.; El-Desoky, E. I. Synthesis and Computational Analysis of New Antioxidant and Antimicrobial Angular Chromenopyrimidines. J. Heterocy. Chem. 2019, 56, 2922–2933. DOI: 10.1002/jhet.3686.
  • Tomer, N.; Malhotra, R. Schiff Base as a Fluorescent Sensor Derived from Chromone Moiety for the Effective Detection of Zn(II) Ions. J. Mol. Struct. 2022, 1252, 132124. DOI: 10.1016/j.molstruc.2021.132124.
  • Gomha, S. M.; Edrees, M. M.; Muhammad, Z. A.; Kheder, N. A.; Abu- Melha, S.; Saad, A. M. Synthesis, Characterization, and Antimicrobial Evaluation of Some New 1,4-Dihydropyridines-1,2,4-Triazole Hybrid Compounds. Polycyc. Arom. Compds 2022, 42, 173–185. DOI: 10.1080/10406638.2020.1720751.
  • Kamel, M. M.; Abdo, N. Y. M. Synthesis of Novel 1,2,4-Triazoles, Triazolothiadiazines and Triazolothiadiazoles as Potential Anticancer Agents. Eur. J. Med. Chem. 2014, 86, 75–80. DOI: 10.1016/j.ejmech.2014.08.047.
  • Ullah, S.; Waqas, M.; Halim, S. A.; Khan, I.; Khalid, A.; Abdalla, A. N.; Makeen, H. A.; Ibrar, A.; Khan, A.; Al-Harras, A. Triazolothiadiazoles and Triazolothiadiazines as Potent α-Glucosidase Inhibitors: Mechanistic Insights from Kinetics Studies, Molecular Docking and Dynamics Simulations. Int. J. Biol. Macromol. 2023, 250, 126227. DOI: 10.1016/j.ijbiomac.2023.12622.
  • Alshareef, F. M.; Al-Harbi, S. A.; Allehyani, E. S.; Abdullah, O.; Ibrahim, M. A. Design, Synthesis and Antimicrobial Activity of Heteroannulated Chromeno[3′,2′:5,6] Pyrido[2,3-d][1,3]Thiazolo[3,2-a]Pyrimidines. Synth. Commun. 2024, 54, 133–143. DOI: 10.1080/00397911.2023.2287654.
  • Badran, A.; Ahmed, A.; Nabeel, A. I.; Ibrahim, M. A. Ring Opening Ring Closure Reactions with 5,9-Diethyl-7-(Chromon-3-yl)-7-Hydroquinolino[3′,4′:5,6]Pyrano[3,2-c]Quinoline-6,8(5H,9H)-Dione with Some 1,2-Binucleophiles: Synthesis, Characterization, DFT Study and Biological Activity. J. Mol. Struct. 2024, 1298, 137030. DOI: 10.1016/j.molstruc.2023.137030.
  • Alshaye, N. A.; Ibrahim, M. A.; Badran, A. Nucleophilic Transformation of 3-Substituted-6,8-Dimethylchromones with Phenylhydrazine under Various Reaction Conditions: Theoretical, Spectroscopic Characterization and in Silico ADME Studies. J. Mol. Struct. 2024, 1297, 137006. DOI: 10.1016/j.molstruc.2023.137006.
  • Nohara, A.; Ishiguro, T.; Ukawa, K.; Sugihara, H.; Maki, Y.; Sanno, Y. Studies on Antianaphylactic Agents. 7. Synthesis of Antiallergic 5-Oxo-5H-[1]Benzopyrano[2,3-b]Pyridines. J. Med. Chem. 1985, 28, 559–568. DOI: 10.1021/jm50001a005.
  • Ibrahim, M. A.; El-Gohary, N. M.; Ibrahim, S. S.; Said, S. Synthesis of Some Novel Heteroannelated Chromones by Basic Rearrangement of 6-Methylchromone-3-Carbonitrile. Chem. Heterocycl. Comp. 2015, 50, 1624–1633. DOI: 10.1007/s10593-014-1632-y.
  • Abdel Hamid, A. M.; Hamed, E. O. Synthesis and Fluorescent Properties of Some Furan-Tagged Thieno[2,3-d]Pyrimidines and Thieno[2,3-d,4,5-d’]Dipyrimidines. J. Heterocy. Chem. 2020, 57, 2194–2202. DOI: 10.1002/jhet.3939.
  • Ibrahim, M. A.; Al-Harbi, S. A.; Allehyani, E. S.; Alqurashi, E. A.; Alshareef, F. M. First Synthesis of the Novel Triazolo[3,4-b][1,3,4]Thiadiazoles and Triazolo[3,4-b][1,3,4]Thiadiazines Linked Chromeno[2,3-b]Pyridine. Polycyclic Arom. Compds 2024, 44, 361–374. DOI: 10.1080/10406638.2023.2173621.
  • El-Wakil, M. H.; El-Yazbi, A. F.; Ashour, H. M. A.; Khalil, M. A.; Ismail, K. A.; Labouta, I. M. Discovery of a Novel DNA Binding Agent via Design and Synthesis of New Thiazole Hybrids and Fused 1,2,4-Triazines as Potential Antitumor Agents: Computational, Spectrometric and in Silico Studies. Bioorg. Chem. 2019, 90, 103089. DOI: 10.1016/j.bioorg.2019.103089.
  • Gould, J. C.; Bowie, J. M. The Determination of Bacterial Sensitivity to Antibiotics. Edinb. Med. J. 1952, 59, 178–199.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.