Clove (Eugenia Caryophyllata) Extraction and Synthesis of New Pyrazole Derivatives from Eugenol

§ Faculty Science and Technology, University Sultan Mo...

Send Message

To: Author

Clove (Eugenia Caryophyllata) Extraction and Synthesis of New Pyrazole Derivatives from Eugenol

Article Fingerprint

ReserarchID

1ZAN4

Clove (Eugenia Caryophyllata) Extraction and Synthesis of New Pyrazole Derivatives from Eugenol Banner

Key Research Insights

Synthesized scholarly intelligence & interactive research assistant
  • English
  • Afrikaans
  • Albanian
  • Amharic
  • Arabic
  • Armenian
  • Azerbaijani
  • Basque
  • Belarusian
  • Bengali
  • Bosnian
  • Bulgarian
  • Catalan
  • Cebuano
  • Chichewa
  • Chinese (Simplified)
  • Chinese (Traditional)
  • Corsican
  • Croatian
  • Czech
  • Danish
  • Dutch
  • Esperanto
  • Estonian
  • Filipino
  • Finnish
  • French
  • Frisian
  • Galician
  • Georgian
  • German
  • Greek
  • Gujarati
  • Haitian Creole
  • Hausa
  • Hawaiian
  • Hebrew
  • Hindi
  • Hmong
  • Hungarian
  • Icelandic
  • Igbo
  • Indonesian
  • Irish
  • Italian
  • Japanese
  • Javanese
  • Kannada
  • Kazakh
  • Khmer
  • Korean
  • Kurdish (Kurmanji)
  • Kyrgyz
  • Lao
  • Latin
  • Latvian
  • Lithuanian
  • Luxembourgish
  • Macedonian
  • Malagasy
  • Malay
  • Malayalam
  • Maltese
  • Maori
  • Marathi
  • Mongolian
  • Myanmar (Burmese)
  • Nepali
  • Norwegian
  • Pashto
  • Persian
  • Polish
  • Portuguese
  • Punjabi
  • Romanian
  • Russian
  • Samoan
  • Scots Gaelic
  • Serbian
  • Sesotho
  • Shona
  • Sindhi
  • Sinhala
  • Slovak
  • Slovenian
  • Somali
  • Spanish
  • Sundanese
  • Swahili
  • Swedish
  • Tajik
  • Tamil
  • Telugu
  • Thai
  • Turkish
  • Ukrainian
  • Urdu
  • Uzbek
  • Vietnamese
  • Welsh
  • Xhosa
  • Yiddish
  • Yoruba
  • Zulu
Reading Preferences
Font Size
Line Spacing
Background
This converted HTML version may contain rendering inconsistencies. Please refer to the PDF for the authoritative version, or click here to provide feedback.

Abstract

An efficient method for the preparation of novel 1,3,4-trisubstituted 4,5-dihydro-1H- pyrazoles via 1,3-dipolar cycloaddition has been described. Using this method, various pyrazole were synthesized from eugenol, a major phenolic constituent of clove bud essential oil, as dipolarophilic system and N-aryl-C-ethoxycarbonitrilimine: the (Z)-ethyl 2-bromo-2-(2-(4chlorophenyl)-hydrazono) acetate.

References

60 Cites in Article
  1. 1. G Gilbertson,R Koenig (1981). Unknown Title. Anal. Chem, 53, 61R-77R.
  2. 2. Mauro Marotti,Roberta Piccaglia,Enrico Giovanelli (1996). Differences in Essential Oil Composition of Basil (Ocimum basilicum L.) Italian Cultivars Related to Morphological Characteristics. Journal of Agricultural and Food Chemistry, 44(12), 3926-3929.
  3. 3. Kenneth Markowitz,Michael Moynihan,Mintsai Liu,Syngcuk Kim (1992). Biologic properties of eugenol and zinc oxide-eugenol. Oral Surgery, Oral Medicine, Oral Pathology, 73(6), 729-737.
  4. 4. M Asha,D Prashanth,B Murali,R Padmaja,A Amit (2001). Anthelmintic activity of essential oil of Ocimum sanctum and eugenol. Fitoterapia, 72(6), 669-670.
  5. 5. G Kamatou,I Vermaak,A Viljoen (2012). Unknown Title. Molecules, 17, 6953.
  6. 6. G Delogu,D Fabbri,M Dettori,A Forni,G Casalone (2004). Unknown Title. Tetrahedron: Asymmetry, 15, 275.
  7. 7. J Usta,S Kreydiyyeh,P Barnabe,Y Bou-Moughlabay,H Nakkash-Chmaisse (2003). Unknown Title. Hum. Exp. Toxicol, 22, 355.
  8. 8. M Hattori,S Hada,A Watahiki,H Ihara,Y.-Z Shu,N Kakiuchi,T Mizuno,T Namba (1986). Unknown Title. Chem. Pharm. Bull, 34, 3885.
  9. 9. M Himejima,I Kubo (1992). Unknown Title. J. Nat. Prod, 55, 620.
  10. 10. S Fujisawa,T Atsumi,K Satoh,H Sakagami (2003). Unknown Title. J. Dent. Res, 82, 43.
  11. 11. T Ohkubo,M Shibata (1997). The Selective Capsaicin Antagonist Capsazepine Abolishes the Antinociceptive Action of Eugenol and Guaiacol. Journal of Dental Research, 76(4), 848-851.
  12. 12. Nedyalka Yanishlieva,Emma Marinova (2001). Stabilisation of edible oils with natural antioxidants. European Journal of Lipid Science and Technology, 103(11), 752-767.
  13. 13. P Suppakul,J Miltz,K Sonneveld,S Biger (2003). Unknown Title. J. Agric. Food Chem, 51, 3197.
  14. 14. Seiichiro Fujisawa,Toshiko Atsumi,Yoshinori Kadoma,Hiroshi Sakagami (2002). Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology, 177(1), 39-54.
  15. 15. Myung-Bok Wie,Moo-Ho Won,Keun-Ho Lee,Joon-Hyun Shin,Jae-Chul Lee,Hong-Won Suh,Dong-Keun Song,Yung-Hi Kim (1997). Eugenol protects neuronal cells from excitotoxic and oxidative injury in primary cortical cultures. Neuroscience Letters, 225(2), 93-96.
  16. 16. M Sayyah,J Valizadeh,M Kamalinejad (2002). Anticonvulsant activity of the leaf essential oil of Laurus nobilis against pentylenetetrazole- and maximal electroshock-induced seizures. Phytomedicine, 9(3), 212-216.
  17. 17. Moo Won,Jae Lee,Yung Kim,Dong Song,Hong Suh,Yang Oh,Jung Kim,Tae Shin,Young Lee,Myung Wie (1998). Postischemic hypothermia induced by eugenol protects hippocampal neurons from global ischemia in gerbils. Neuroscience Letters, 254(2), 101-104.
  18. 18. Y Irie,W Keung (2003). Unknown Title. Brain Res, 963, 282.
  19. 19. Yoshifumi Irie,Nanae Itokazu,Naoko Anjiki,Atsushi Ishige,Kenji Watanabe,Wing Keung (1011). Eugenol exhibits antidepressant-like activity in mice and induces expression of metallothionein-III in the hippocampus. Brain Research, 1011(2), 243-246.
  20. 20. K Sumeet,K Vivek,V Raksh (2006). Contents. Journal of Molecular Catalysis A: Chemical, 245(1-2), v-xiv.
  21. 21. J Nicholas,A Narbad,B Craig,G Williamson (2000). Unknown Title. Current Opinion in Biotechnology, 11, 490.
  22. 22. B Souza,P Dayse,T Alini,M Heiddy,C Gisele,H Olsen Mara,C Lucio,O Antunes (2007). Unknown Title. Catalysis Communications, 8, 1041.
  23. 23. S Kei,K Yoko,N Tomohisa,H Hatsuyuki,N Nobuyoshi,H Hiroki (2006). Unknown Title. Phytochemistry, 7, 2256.
  24. 24. M Camacho,J Leon,A Entrena,G Velasco,M Carrion,G Escames,A Vivo,D Castroviejo,M Gallo,A Espinosa (2004). Unknown Title. J. Med. Chem, 47, 5641.
  25. 25. John Goodell,Francesc Puig-Basagoiti,Brett Forshey,Pei-Yong Shi,David Ferguson (2006). Identification of Compounds with Anti-West Nile Virus Activity. Journal of Medicinal Chemistry, 49(6), 2127-2137.
  26. 26. S Schenone,C Brullo,O Bruno,F Bondavalli,L Mosti,G Maga,E Crespan,F Carraro,F Manetti,C Tintori,M Botta,Eur (2008). Unknown Title. J. Med. Chem, 43, 2665.
  27. 27. Bertrand Cottineau,Patrick Toto,Christophe Marot,Aline Pipaud,Jacques Chenault (2002). Synthesis and hypoglycemic evaluation of substituted pyrazole-4-carboxylic acids. Bioorganic & Medicinal Chemistry Letters, 12(16), 2105-2108.
  28. 28. Ka Lee,Jeong Kim,Jae Kim (2003). Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis–Hillman adducts. Tetrahedron Letters, 44(35), 6737-6740.
  29. 29. W John,R Patera,M Plummer,B Halling,D Yuhas (1994). Unknown Title. Pest. Sci, 42, 29.
  30. 30. L Goodman,A Gilman (1980). The Pharmacological Basis of Therpeutics. The Pharmacological Basis of Therpeutics
  31. 31. H Patel,K Vyas,P Fernandes (1990). ChemInform Abstract: Synthesis of Substituted 6‐(3′,5′‐Dimethyl‐1H‐pyrazol‐1′‐yl)quinolines and Evaluation of Their Biological Activities. ChemInform, 21(50), 966.
  32. 32. H Patel,K Vyas,P Fernandes (1990). ChemInform Abstract: Synthesis of Substituted 6‐(3′,5′‐Dimethyl‐1H‐pyrazol‐1′‐yl)quinolines and Evaluation of Their Biological Activities. ChemInform, 21(50), 836.
  33. 33. H Patel,K Vyas,P Fernandes,Indian (1989). Unknown Title. J. Chem, 28, 470.
  34. 34. H Patel,K Vyas,P Fernandes,Indian (1989). Care of low birth weight babies in slums. The Indian Journal of Pediatrics, 56(2), 231-237.
  35. 35. S Fadel,Y Rakib,E Khouili,M Pujol,M Guillaumet,G (2004). Unknown Title. Synth. Commun, 34.
  36. 36. S Fadel,S Hamri,Y Hajbi,F Suzenet,A Hafid,E Rakib,M Khouili,M Pujol,G Guillaumet,Arkivoc (2011). Unknown Title.
  37. 37. A Padwa,W Pearson (2003). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products
  38. 38. P Pérez,L Domingo,M Aurell,R Contreras (2003). Unknown Title. Tetrahedron, 59, 3117.
  39. 39. Qun Dang,Brian Brown,Mark Erion (1996). 5-Aminopyrazoles as Dienophiles in the Inverse Electron Demand Diels−Alder Reactions of 2,4,6-Tris(ethoxy- carbonyl)-1,3,5-triazine: Syntheses of Pyrazolopyrimidines. The Journal of Organic Chemistry, 61(16), 5204-5205.
  40. 40. Nuno Moura,F Giuntini,Maria Faustino,Maria Neves,Augusto Tomé,Artur Silva,E Rakib,A Hannioui,S Abouricha,Beate Röder,José Cavaleiro (2010). 1,3-Dipolar cycloaddition of nitrile imines to meso-tetraarylporphyrins. Arkivoc, 2010(5), 24-33.
  41. 41. Ahmad Shawali,Thoraya Farghaly,Ahmad Aldahshoury (2010). An efficient synthesis of functionalized 3-(hetaryl)pyrazoles. Arkivoc, 2010(9), 19-30.
  42. 42. D Babinski,H Aguilar,R Still,D Frantz (2011). Unknown Title. J. Org. Chem, 76, 5915.
  43. 43. A Shawali,N Samy (2009). The Open Bioactive. Compd. J, 2, 8.
  44. 44. A Shawali,Current (2010). Unknown Title. Org. Chem, 14, 784.
  45. 45. Tasir Haque,Seifu Tadesse,Jovita Marcinkeviciene,M Rogers,Christine Sizemore,Lisa Kopcho,Karen Amsler,Lisa Ecret,Dong Zhan,Frank Hobbs,Andrew Slee,George Trainor,Andrew Stern,Robert Copeland,Andrew Combs (2002). Parallel Synthesis of Potent, Pyrazole-Based Inhibitors of Helicobacter pylori Dihydroorotate Dehydrogenase. Journal of Medicinal Chemistry, 45(21), 4669-4678.
  46. 46. J Pfifferkorn (2008). Unknown Title. J. Med. Chem, 51, 31.
  47. 47. Z Sweeney (2008). Unknown Title. J. Med. Chem, 51, 7449.
  48. 48. J Bouali,K Rhazri,S Hamri,J Zaiter,H Ouchetto,A Hafid,H El Batal,A Hasib,M Khouili (2013). Unknown Title. Chemical and Process Engineering Research, 12, 19-27.
  49. 49. Dexter Sharp,Cliff Hamilton (1946). Derivatives of 1,2,4-Triazole and of Pyrazole. Journal of the American Chemical Society, 68(4), 588-591.
  50. 50. A Enayati,H Vatandoosty,H Ladonniy,H Townson,Hemingway (2003). Unknown Title. J. Medical and Veterinary Entomology, 17, 138.
  51. 51. A Lynd,H Ranson,P Mccall,N Randle,I Black,W Walker,E Donnelly,M (2005). Unknown Title. Malaria Journal, 4, 1.
  52. 52. Willem Takken (1022). Do insecticide‐treated bednets have an effect on malaria vectors?. Tropical Medicine & International Health, 7(12), 1022-1030.
  53. 53. Bhupinder Khambay,V Chandre,F Hougard,J (2002). Pyrethroid Insecticides. Pesticide Outlook, 13(2), 49-54.
  54. 54. R Gazzaeva,S Mochalov,B Archegov,N Zefirov (2005). Isoxazolines from Benzyl Cyclopropanes. Chemistry of Heterocyclic Compounds, 41(2), 272-272.
  55. 55. Frieder Gnad,Oliver Reiser (2003). Synthesis and Applications of β-Aminocarboxylic Acids Containing a Cyclopropane Ring. Chemical Reviews, 103(4), 1603-1624.
  56. 56. Pietruszka (2003). Unknown Title. J. Chem. Rev, 103, 1051.
  57. 57. S Bakunov,A Rukavishnikov,A Tkachev (1994). Unknown Title. Synthesis, 935.
  58. 58. P Lee,J Kim,Y Kim,S Kim (1993). Unknown Title. Tetrahedron Letters, 34, 7583.
  59. 59. Gerald Hammond,Marilyn Cox,David Wiemer (1990). Sterocontrol in Horner-Wadsworth-Emmons condensations of a gem-dimethylcyclopropyl aldehyde with .alpha.-substituted phosphono acetates. The Journal of Organic Chemistry, 55(1), 128-132.
  60. 60. Dieter Arlt,Manfred Jautelat,Reinhard Lantzsch (1981). Syntheses of Pyrethroid Acids. Angewandte Chemie International Edition in English, 20(9), 703-722.

Funding

No external funding was declared for this work.

Conflict of Interest

The authors declare no conflict of interest.

Ethical Approval

No ethics committee approval was required for this article type.

Data Availability

Not applicable for this article.

How to Cite This Article

M. Khouili. 2013. "Clove (Eugenia Caryophyllata) Extraction and Synthesis of New Pyrazole Derivatives from Eugenol". Global Journal of Science Frontier Research - B: Chemistry GJSFR-B Volume 13 (GJSFR Volume 13 Issue B7).

More Citation Formats

Download Citation

Journal Specifications

Crossref Journal DOI 10.17406/GJSFR

Print ISSN 0975-5896

e-ISSN 2249-4626

Keywords
Classification
GJSFR-B Classification FOR Code: 640402
030306
Version of record

v1.2

Issue date
December 25, 2013

Language
English
Order Article Reprint
Experience in AR

Explore published articles in an immersive Augmented Reality environment. Our platform converts research papers into interactive 3D books, allowing readers to view and interact with content using AR and VR compatible devices.

Read in 3D

Your published article is automatically converted into a realistic 3D book. Flip through pages and read research papers in a more engaging and interactive format.

Article Matrices
Total Views: 1.7K
Total Downloads: 104
All Trends

Request Access

Please fill out the form below to request access to this research paper. Your request will be reviewed by the editorial or author team.
X

This is the heading

Lorem ipsum dolor sit amet, consectetur adipiscing elit. Ut elit tellus, luctus nec ullamcorper mattis, pulvinar dapibus leo.

High-quality academic research articles on global topics and journals.

Clove (Eugenia Caryophyllata) Extraction and Synthesis of New Pyrazole Derivatives from Eugenol

M. Khouili
M. Khouili Faculty Science and Technology, University Sultan Moulay Slimane