European Journal of Chemistry 2015, 6(1), 21-30 | doi: https://doi.org/10.5155/eurjchem.6.1.21-30.1137 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene


Enis Ben Bnina (1) , Anis Romdhane (2) , Majda Daami-Remadi (3) , Hichem Ben Jannet (4,*)

(1) Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
(2) Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
(3) UR13AGR09, Production Horticole Intégrée au Centre Est Tunisien, Centre Régional des Recherches en Horticulture et Agriculture Biologique de Chott-Mariem, Université de Sousse, 4042, Chott-Mariem, Tunisie
(4) Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Equipe: Chimie Médicinale et Produits Naturels, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisie
(*) Corresponding Author

Received: 22 Aug 2014 | Accepted: 19 Sep 2014 | Published: 31 Mar 2015 | Issue Date: March 2015

Abstract


We report herein the convenient procedures for the efficient and easy synthesis, and the antimicrobial and the anti-acetylcholinesterase evaluation of two new series of (R)-limonene derivatives. A substantial modification aimed at targeting to discover novel structures with a better antimicrobial and anti-acetylcholinesterase (anti-AChE) activities. The condensation of (R)-limonene (1) with various arylnitrile oxides led, via the 1,3-dipolar cycloaddition reaction, conducted with complete region-specificity, to a series of new limonene-dihydroisoxazoles, 2a-h. On the other hand, N-alkylation of the previously prepared limonene-lactam derivative (3) yielded the corresponding dipolarophile (4), which affords by condensation with arylnitrile oxides the expected new dihydroisoxazoles, 5a-h. The target compounds were completely characterized by 1H NMR, 13C NMR and MS. All the synthesized heterocyclic compounds were tested for their antimicrobial and anti-acetylcholinesterase activities. The dihydroisoxazoles 2a (IZ = 13.25 mm, cc = 1 mg/mL) and 5b (IZ = 13.75 mm, cc = 1 mg/mL) exhibited the highest antifungal activity. The greatest anti-acetylcolinesterase activity was exhibited by 2f (IC50 = 82±3 µg/mL) and by 5a (IC50 = 99±1 µg/mL).


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and May 31, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Lactam; (R)-Limonene; Antimicrobial; Cycloaddition; Dihydroisoxazoles; Anti-acetylcholinesterase

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.6.1.21-30.1137

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1683 times | icon graph PDF Article downloaded 580 times

Funding information


The Ministry of Higher Education, Scientific Research and Technology, Tunisia

Citations

/


[1]. Abdel-Zaher Abdel-Aziz Elassar
An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity
European Journal of Chemistry  6(4), 387, 2015
DOI: 10.5155/eurjchem.6.4.387-393.1306
/


References


[1]. Guenther, A.; Geron, C.; Pierce, T.; Brian, L.; Harley, P.; Fall, R. Atmos. Environ. 2000, 234, 2205-2230.
http://dx.doi.org/10.1016/S1352-2310(99)00465-3

[2]. Crowell, P. L. J. Nutr. 1999, 129, 775S-778S.

[3]. Singh, P.; Shukla, R.; Prakash, B.; Kumar, A.; Singh, S.; Mishra, P. K.; Dubey, N. K. Food Chem. Toxicol. 2010, 48, 1734-1740.
http://dx.doi.org/10.1016/j.fct.2010.04.001

[4]. Ferrarini, S. R.; Duarte, M. O.; DaRosa, R. G.; Rolim, V.; EiflerLima, V. L.; VonPose, G.; Ribeiro, V. L. S. Vet. Parasitol. 2008, 157, 149-153.
http://dx.doi.org/10.1016/j.vetpar.2008.07.006

[5]. Elson, C. E.; Maltzman, T. H.; Boston, J. L.; Tanner, M. A.; Gould, M. N. Carcinogenesis 1988, 9, 331-332.
http://dx.doi.org/10.1093/carcin/9.2.331

[6]. Elegbede, J. A.; Maltzman, T. H.; Verma, A. K.; Tanner, M. A.; Elson, C. E.; Gould, M. N. Carcinogenesis 1999, 7, 2047-2049.
http://dx.doi.org/10.1093/carcin/7.12.2047

[7]. Dietrich, D. R.; Swenberg, J. A. Cancer. Re.s 1991, 51, 3512-3521.

[8]. Wattenberg, L. W.; Coccia, J. B. Carcinogenesis 1991, 12, 115-117.
http://dx.doi.org/10.1093/carcin/12.1.115

[9]. Nakaizumi, A.; Baba, M.; Uehara, H.; Iishi, H.; Tatsuta, M. Cancer Lett. 1997, 117, 99-103.
http://dx.doi.org/10.1016/S0304-3835(97)00207-3

[10]. Chen, J.; Lu, M.; Jing, Y.; Dong, J. J. Bioorg. Med. Chem. 2006, 14, 6539-6547.
http://dx.doi.org/10.1016/j.bmc.2006.06.013

[11]. Maltzman, T. H.; Hurt, L. M.; Elson, C. E.; Tanner, M. A.; Gould, M. N. Carcinogenesis 1989, 10, 781-783.
http://dx.doi.org/10.1093/carcin/10.4.781

[12]. Yang, Y. Q.; Zhao, G. Chem. Eur. J. 2008, 14, 10888-10891.
http://dx.doi.org/10.1002/chem.200801749

[13]. Cimarelli, C.; Fratoni, D.; Palmieri, G. Tetrahedron-Asymmetr. 2009, 20, 2234-2239.
http://dx.doi.org/10.1016/j.tetasy.2009.08.012

[14]. Hensen, K.; Mahaim, C.; Holderich, W. F. Appl. Catal. A-Gen. 1997, 149, 311-329.
http://dx.doi.org/10.1016/S0926-860X(96)00273-6

[15]. Chang, S. S.; Peterson, R. J. J. Food Sci. 1977, 42, 298-305.
http://dx.doi.org/10.1111/j.1365-2621.1977.tb01486.x

[16]. Midori, A. A.; Toshio, S.; Takayoshi, A.; Hiroaki, S. Yuki Gosei Kagaku Kyokaishi 2004, 62, 59-69.
http://dx.doi.org/10.5059/yukigoseikyokaishi.62.59

[17]. Quadrelli, P.; Scrocchi, R.; Caramella, P.; Rescifina, A.; Piperno, P. Tetrahedron 2004, 60, 3643-3651.
http://dx.doi.org/10.1016/j.tet.2004.02.057

[18]. Lam, P. Y. S.; Adams, J. J.; Clark, C. G.; Calhoun, W. J.; Luettgen, J. M.; Knabb, R. M.; Wexler, R. R. Bioorg. Med. Chem. Lett. 2003, 13, 1795-99.
http://dx.doi.org/10.1016/S0960-894X(03)00130-6

[19]. Kai, H.; Mastsumoto, H.; Hattori, N.; Takase, A.; Fujiwara, T.; Sugimoto, H. Bioorg. Med. Chem. Lett. 2001, 11, 1997-2000.
http://dx.doi.org/10.1016/S0960-894X(01)00362-6

[20]. Tangallapally, R. P.; Sun, D.; Rakesh; Budha, N.; Lee, R. E.; Lenaerts, A. J.; Meibohm, B.; Lee, R. E. Bioorg. Med. Chem. Lett. 2007, 17, 6638-6642.
http://dx.doi.org/10.1016/j.bmcl.2007.09.048

[21]. Jadhav, S. B.; Shastri; R. A.; Gaikwad, K. V.; Gaikwad, S. V. E-J. Chem. 2009, 6(S1), S183-S188.

[22]. Jayashankara, B.; LokanathaRai, K. M. Arkivoc 2008, 11, 75-85.
http://dx.doi.org/10.3998/ark.5550190.0009.b07

[23]. Prasad, Y. R.; Ravikumar, P.; Ramesh, B. Int. J. Chem. Sci. 2007, 5, 542-548.

[24]. Amici, M. D.; Conti, P.; Vistoli, G.; Carrea, G.; Ottolina, G.; DeMicheli, C. Med. Chem. Res. 2001, 10, 615-633.

[25]. Park, K. K.; Ko, D. H.; You, Z.; Khan, M. O.; Lee, H. J. Steroids 2006, 71, 183-188.
http://dx.doi.org/10.1016/j.steroids.2005.10.003

[26]. Hwang, I. T.; Kim, H. R.; Jeon, J. D.; Hong, K. S.; Song, J. H.; Cho, K. Y. J. Agric. Food Chem. 2005, 53, 8639-8643.
http://dx.doi.org/10.1021/jf051284f

[27]. Li, X. F.; Feng, Y. Q.; Xu, M. Acta. Crystallogr. E 2003, 59, O675-O676.
http://dx.doi.org/10.1107/S1600536803008134

[28]. Pedro, A. C.; Volker, J.; Albrecht, L.; Rodolfo, D. B. Tetrahedron 2003, 44, 1071-1074.
http://dx.doi.org/10.1016/S0040-4039(02)02665-5

[29]. Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247-12275.
http://dx.doi.org/10.1016/j.tet.2007.09.065

[30]. Pellissier, H. Tetrahedron 2007, 63, 3235-3285.
http://dx.doi.org/10.1016/j.tet.2007.01.009

[31]. Feddaoui, A.; AitItto, M. Y.; AitAli, M.; Hasnoui, A.; Riahi, A. Synth. Commun. 2006, 36, 3617-3624.

[32]. Clemett, D.; Markham, A. Drugs 2000, 59, 815-827.
http://dx.doi.org/10.2165/00003495-200059040-00007

[33]. GarciaMoreno, M. I.; DiazPérez, P.; Ortiz, M. C.; Garcia, F. J. M. J. Org. Chem. 2003, 68, 8890-8901.

[34]. Dighade, S. R.; Patil, S. D.; Chincholkar, M. M.; Dighade, N. R. Asian J. Chem. 2003, 15, 450-454.

[35]. Barbachyn, M. R.; Cleek, G. J.; Dolak, L. A.; Garmon, S. A.; Morris, J.; Seest, E. P.; Thomas, R. C.; Toops, D. S.; Watt, W.; Wishka, D. G.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H.; Adams, W. J.; Friis, J. M.; Slatter, J. P.; Oien, N. L.; Zaya, M. J.; Wienkers, L. C.; Wynalda, M; A. J. Med. Chem. 2003, 46, 284-302.
http://dx.doi.org/10.1021/jm020248u

[36]. Basappa, Sadashiva, M. P.; Mantelingu, K.; Nanjunda, S. S.; Rangappa, K. S. Bioorg. Med. Chem 2003, 11, 4539-4544.
http://dx.doi.org/10.1016/j.bmc.2003.08.007

[37]. Gyonfalvi, S.; Szakonyi; Z.; Fulop, F. Tetrahedron-Asymmetr. 2003, 14, 3965-3972.

[38]. Woznica, M.; Butkiewicz, A.; Grzywacz, A.; Kowalska, P.; Masnyk, M.; Michalak, K.; Luboradzki, R.; Furche, F.; Kruse, H.; Grimme, S.; frelek, J. J. Org. Chem. 2011, 76, 3306-3319.

[39]. Alcontres, G. S.; Caristi, C.; Ferlazzo, A.; Gattuso, M. J. Chem. Soc. Perkin Trans. 1976, 1, 1694-1696.
http://dx.doi.org/10.1039/p19760001694

[40]. Harhash, A. H.; Elnagdi, M. H.; Kassab, N. A. L.; Negm, A. M. J. Chem. Eng. Data 1975, 20, 120-122.
http://dx.doi.org/10.1021/je60064a018

[41]. Fale, P. L.; Borges, C.; AmorimMadeira, P. J.; Ascensao, L.; Araujo, M. E. M.; Florencio, M. H.; Serralheiro, M. L. M. Food Chem. 2009, 114, 798-805.

[42]. Orhan, G.; Orhan, I.; Sener, B. Lett. Drug. Des. Discov. 2003, 3, 268-274.
http://dx.doi.org/10.2174/157018006776743215

[43]. Howes, M. J.; Houghton, P. J. Pharmacol. Biochem. Behav. 2003, 75, 513-527.
http://dx.doi.org/10.1016/S0091-3057(03)00128-X


How to cite


Bnina, E.; Romdhane, A.; Daami-Remadi, M.; Jannet, H. Eur. J. Chem. 2015, 6(1), 21-30. doi:10.5155/eurjchem.6.1.21-30.1137
Bnina, E.; Romdhane, A.; Daami-Remadi, M.; Jannet, H. Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene. Eur. J. Chem. 2015, 6(1), 21-30. doi:10.5155/eurjchem.6.1.21-30.1137
Bnina, E., Romdhane, A., Daami-Remadi, M., & Jannet, H. (2015). Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene. European Journal of Chemistry, 6(1), 21-30. doi:10.5155/eurjchem.6.1.21-30.1137
Bnina, Enis, Anis Romdhane, Majda Daami-Remadi, & Hichem Ben Jannet. "Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene." European Journal of Chemistry [Online], 6.1 (2015): 21-30. Web. 29 May. 2023
Bnina, Enis, Romdhane, Anis, Daami-Remadi, Majda, AND Jannet, Hichem. "Novel antimicrobial and anti-acetylcholinesterase dihydroisoxazoles from (R)-limonene" European Journal of Chemistry [Online], Volume 6 Number 1 (31 March 2015)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.6.1.21-30.1137


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2015, 6(1), 21-30 | doi: https://doi.org/10.5155/eurjchem.6.1.21-30.1137 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2023  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.