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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 53, 2023 - Issue 18
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Articles

Synthetic strategies, characterization and antimicrobial evaluation of novel angular heteroannulated furo[3,2-g]chromenes

Pages 1568-1578 | Received 08 Jun 2023, Published online: 24 Jul 2023

References

  • Balbaa, S. I.; Zaki, A. Y.; Abdel-Wahab, S. M. A Micro-Method for the Estimation of Khellin in Presence of Other Constituents of Ammi visnaga Fruits. Planta Med. 1968, 16, 329–334. DOI: 10.1055/s-0028-1099916.
  • Abu-Hashem, A. A.; El-Shazly, M. Synthesis, Reactions and Biological Activities of Furochromones: A Review. Eur. J. Med. Chem. 2015, 90, 633–665. DOI: 10.1016/j.ejmech.2014.12.001.
  • Vanachayangkul, P.; Byer, K.; Khan, S.; Butterweck, V. An Aqueous Extract of Ammi visnaga Fruits and Its Constituents Khellin and Visnagin Prevent Cell Damage Caused by Oxalate in Renal Epithelial Cells. Phytomedicine 2010, 17, 653–658. DOI: 10.1016/j.phymed.2009.10.011.
  • Abu Shady, H. A.; Hassib, S. T.; Mikhael, A. N.; El Ansary, S. L. Synthesis of Some Chromones and Angular Furochromones of Expected Pharmacological Activities. Egypt. J. Pharm. Sci. 1988, 29, 393–407.
  • Abdel-Aal, E. A.; Daosukho, S.; El-Shall, H. Effect of Supersaturation Ratio and Khella Extract on Nucleation and Morphology of Kidney Stones. J. Cryst. Growth 2009, 311, 2673–2681. DOI: 10.1016/j.jcrysgro.2009.02.027.
  • Anrep, G. V.; Kenawy, M. R.; Barsoum, G. S. The Coronary Vasodilator Action of Khellin. Am. Heart J. 1949, 37, 531–542. DOI: 10.1016/0002-8703(49)91131-X.
  • Ibrahim, M. A.; Al-Harbi, S. A.; Allehyani, E. S. Synthesis and Antimicrobial Evaluation of the Novel Heteroannulated Furo[3`,2`:6,7]Chromeno[2,3-b]Pyridines: Part 1. J. Heterocyclic Chem. 2020, 57, 3632–3641. DOI: 10.1002/jhet.4082.
  • Ibrahim, M. A.; Al-Harbi, S. A.; Allehyani, E. S.; Alqurashi, E. A.; Alqarni, A. O. Utility of 3-Chloro-3-(4,9-Dimethoxy-5-Oxo-5H-Furo[3,2-g]Chromen-6-yl)Prop-2-Enal for Construction of Novel Heterocyclic Systems: Synthesis, Characterization, Antimicrobial and Anticancer Evaluation. Synth. Commun. 2022, 52, 608–621. DOI: 10.1080/00397911.2022.2039712.
  • Abu-Hashem, A. A.; Youssef, M. M. Synthesis of New Visnagen and Khellin Furochromone Pyrimidine Derivatives and Their Anti-inflammatory and Analgesic Activity. Molecules 2011, 16, 1956–1972. DOI: 10.3390/molecules16031956.
  • Ragab, F. A.; El-Sayed, N. A.; Eissa, A. A. M.; El Kerdawy, A. M. Synthesis and Anticonvulsant Activity of Certain Substituted Furochromone, Benzofuran and Flavone Derivatives. Chem. Pharm. Bull (Tokyo) 2010, 58, 1148–1156. DOI: 10.1248/cpb.58.1148.
  • Trabalzini, L.; Martelli, P.; Bovalini, L.; Dall’Acqua, F.; Sage, E. Photosensitization of DNA of Defined Sequence by Furochromones, Khellin and Visnagin. J. Photochem. Photobiol. B 1990, 7, 317–336. DOI: 10.1016/1011-1344(90)85165-S.
  • Vedaldi, D.; Caffieri, S.; Dall’Acqua, F.; Andreassi, L.; Bovalini, L.; Martelli, P. Khellin, a Naturally Occurring Furochromone, Used for the Photochemotherapy of Skin Diseases: Mechanism of Action. Farmaco. Sci. 1988, 43, 333–346.
  • Abdel-Fattah, A.; Aboul-Enein, M. N.; Wassel, G. M.; El-Menshawi, B. S. An Approach to the Treatment of Vitiligo by Khellin. Dermatologica 1982, 165, 136–140. DOI: 10.1159/000249932.
  • Abdel-Fattah, A.; Aboul-Enein, M. N.; Wassel, G.; El-Menshawi, B. Preliminary Report on the Therapeutic Effect of Khellin in Psoriasis. Dermatologica 1983, 167, 109–110. DOI: 10.1159/000249760.
  • Akchurin, I. O.; Yakhutina, A. I.; Bochkov, A. Y.; Solovjova, N. P.; Medvedev, M. G.; Traven, V. F. Novel Push-Pull Fluorescent Dyes–7-(Diethylamino)Furo-and Thieno[3,2-c]Coumarins Derivatives: Structure, Electronic Spectra and TD-DFT Study. J. Mol. Struct. 2018, 1160, 215–221. DOI: 10.1016/j.molstruc.2018.01.086.
  • Halim, A.; Ibrahim, S.; Synthesis, M. A. FT-IR, Structural, Thermochemical, Electronic Absorption Spectral, and NLO Analysis of the Novel 10-Methoxy-10H-Furo[3,2-g]Chromeno[2,3-b][1,3]Thiazolo[5,4-e]Pyridine-2,10(3H)-Dione (MFCTP): a DFT/TD-DFT Study. RSC Adv. 2021, 11, 32047–32066., DOI: 10.1039/D1RA06134H.
  • Halim, A.; Ibrahim, S.; Synthesis, M. A. Spectral Analysis, Quantum Studies, NLO, and Thermodynamic Properties of the Novel 5-(6-Hydroxy-4-Methoxy-1-Benzofuran-5-Ylcarbonyl)-6-Amino-3-Methyl-1H-Pyrazolo[3,4-b]Pyridine (HMBPP). RSC Adv. 2022, 12, 13135–13153. DOI: 10.1039/D2RA01469F.
  • Ibrahim, M. A.; Badran, A.; El-Gohary, N. M.; Abdel-Fatah, N. A. Chemical Reactions of Furochromones, Visnagin and Khellin. Heterocycles 2017, 94, 389–440. DOI: 10.3987/REV-16-852.
  • Ibrahim, M. A.; El-Gohary, N. M. Construction and Biological Evaluations of Some Novel Chromeno[2,3-b]Pyridines and Chromeno[2,3-b]Quinolines Using 6-Methylchromone-3-Carbonitrile. Heterocycles 2021, 102, 489–505. DOI: 10.3987/COM-20-14388.
  • Ibrahim, M. A.; Al-Harbi, S. A.; Allehyani, E. S. Synthetic Approach for Building Heteroannulated Furo[3,2-g]Chromenes Using 4,9-Dimethoxy-5-Oxo-5H-Furo[3,2-g]Chromene-6-Carbonitrile and Cyclic Carbon Nucleophiles. Heterocycles 2020, 100, 1450–1462. DOI: 10.3987/COM-20-14294.
  • Ibrahim, M. A.; Al-Harbi, S. A.; Allehyani, E. S. Chemical Transformations with 4,9-Dimethoxy-5-Oxo-5H-Furo[3,2-g]Chromene-6-Carbonitrile: Construction and Antimicrobial Evaluation of the Novel Heteroannulated Furochromenopyridines. Heterocycles 2020, 100, 1172–1188. DOI: 10.3987/COM-20-14273.
  • Ibrahim, M. A.; Al-Harbi, S. A.; Allehyani, E. S. Reactivity of 4,9-Dimethoxy-5-Oxo-5H-Furo[3,2-g]Chromene-6-Carbonitrile Towards Some Nitrogen Nucleophilic Reagents. Heterocycles 2020, 100, 2091–2107. DOI: 10.3987/COM-20-14347.
  • -Gohary, N. M.; Ibrahim, M. A.; El-Sawy, E. R.; Abdel-Fatah, N. A. Chemical Reactivity of 4,9-Dimethoxy-5-Oxo-5H-Furo[3,2-g]Chromene-6-Carboxaldehyde Toward Some Nucleophilic Reagents. J. Heterocyclic Chem. 2017, 54, 1467–1478. DOI: 10.1002/jhet.2733.
  • , M. S.; Deki, B. R.; Deki, V. S.; Deki, S. V. Synthesis and Structure of Novel 3,4-Annelated Coumarin Derivatives. J. Heterocycl. Chem. 2008, 45, 295–297. DOI: 10.1002/jhet.5570450137.
  • El-Sayed, O. A.; Aboul-Enein, H. Y. Synthesis and Antimicrobial Activity of Novel Pyrazolo[3,4-b]Quinoline Derivatives. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 117–120. DOI: 10.1002/1521-4184(200104)334:4<117::AID-ARDP117>3.0.CO;2-9.
  • El-Dean, A. M. K.; 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. Bioorg. Chem. 2013, 39, 553–564. DOI: 10.1134/S1068162013040079.
  • Chandra, A.; Upadhyay, S.; Singh, B.; Sharma, N.; Singh, R. M. Base-Catalyzed Cyclization Reaction of 2-Chloroquinoline-3-Carbonitriles and Guanidine Hydrochloride: A Rapid Synthesis of 2-Amino-3H-Pyrimido[4,5-b]Quinolin-4-Ones. Tetrahedron 2011, 67, 9219–9224. DOI: 10.1016/j.tet.2011.09.032.
  • Gould, J. C.; Bowie, J. M. The Determination of Bacterial Sensitivity to Antibiotics. Edinb. Med. J. 1952, 59, 178–199.

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