European Journal of Chemistry 2011, 2(4), 539-543 | doi: https://doi.org/10.5155/eurjchem.2.4.539-543.55 | Get rights and content

Issue cover





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

Synthesis and biological activity of functionalized phosphorus derivatives of isatin imines


Emtithal Ahmed El-Sawi (1,*) , Tahia Bayoumy Mostafa (2) , Hyam Ali Radwan (3)

(1) Chemistry Department, Faculty of Girls for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, 11757, Egypt
(2) Chemistry Department, Faculty of Girls for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, 11757, Egypt
(3) Chemistry Department, Faculty of Girls for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, 11757, Egypt
(*) Corresponding Author

Received: 11 Apr 2010 | Revised: 07 May 2010 | Accepted: 05 Jun 2010 | Published: 31 Dec 2011 | Issue Date: December 2011

Abstract


Isatin-3-imine derivatives (1a-d) have been synthesized. These compounds were then converted into phosphorylated products 2a, 2c with triethylphosphite and 3a-d with triphenylphosphine. The structures of the new compounds were confirmed by elemental analyses, IR, UV/VIS, 1H NMR, 13C NMR and MS studies. The structure of compound 1a was also confirmed by single crystal X-ray diffraction studies. Compounds 1b-d and 3c-d exhibited potent antibacterial activity against Bacillus subtilis and Escherichia Coli. Compound 3a was found to exhibit antifungal activity against the tested organisms.

2_4_539_543_800


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).


Editor-in-Chief
European Journal of Chemistry

Keywords


Mass spectroscopy; Phosphorylation; Triphenylphosphine; Schiff bases; X-ray crystallography; Antimicrobial activity

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.2.4.539-543.55

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1681 times | icon graph PDF Article downloaded 827 times


Citations

/


[1]. V. U. Bhaskara Rao, Amol P. Jadhav, Dnyaneshwar Garad, Ravi P. Singh
Asymmetric Vinylogous Mannich Reaction of Silyloxy Furans with N-tert-Butanesulfinyl Ketimines
Organic Letters  16(3), 648, 2014
DOI: 10.1021/ol4037117
/


[2]. Pedro Henrique do Nascimento Pereira, Jackelinne Camargo Lima, Victor Marcelo Deflon, Geoffroy Roger Pointer Malpass, Ronaldo Junio De Oliveira, Pedro Ivo Da Silva Maia
Nitroisatin dithiocarbazate: Synthesis, structural characterization, DFT, and docking studies
European Journal of Chemistry  12(3), 235, 2021
DOI: 10.5155/eurjchem.12.3.235-241.2106
/


[3]. Mona Hizkial Nasr Arsanious, Soher Said Maigali
Isatin Imines in the Reaction with Iminophosphine: X-Ray Structure of Phospholane Derivatives
Synthetic Communications  44(2), 202, 2014
DOI: 10.1080/00397911.2013.800210
/


[4]. Ivan Hameed Rouil Tomi, Amer Hasan Abdullah, Ali Hussein Raheemah Al-Daraji, Selma Abdul Rudha Abbass
Synthesis, characterization and comparative study the antibacterial activities of some imine-amoxicillin derivatives
European Journal of Chemistry  4(2), 153, 2013
DOI: 10.5155/eurjchem.4.2.153-156.751
/


[5]. Muhammad Islam, Zahid Shafiq, Mazhar Hussain, Hafiz Badaruddin Ahmad, Muhammad Ajaz Hussain
Synthesis, characterization and antimicrobial studies of imine derivatives of amoxicillin
European Journal of Chemistry  6(4), 417, 2015
DOI: 10.5155/eurjchem.6.4.417-421.1310
/


References


[1]. Huber, S. M.; Hennig, A.; Puhlhofer, F. G.; Weiss R. J. Heterocycl. Chem. 2009, 46, 421-427.
http://dx.doi.org/10.1002/jhet.8

[2]. Raghunathan, R.; Ramesh, E.; Elamparuthi, E. Lett. Org. Chem. 2008, 5, 82-86.
http://dx.doi.org/10.2174/157017808783743948

[3]. Un, R.; Ikizler, A. A. Chim. Acta Turc. 1975, 3, 1-22.

[4]. Milcent, R.; Redeuilh, C. J. Heterocycl. Chem. 1979, 16, 403-407.
http://dx.doi.org/10.1002/jhet.5570160245

[5]. Islam, M. R.; Abedin, M. J.; Hossain M. M.; Duddeck, H. J. Bangladesh Chem. Soc. 1998, 11, 71-78.

[6]. Sarangapani, M.; Reddy, V. M. Indian J. Pharm. Sci. 1994, 56, 174-177.

[7]. Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Pharm. Acta Helv. 1999, 74, 11-17.
http://dx.doi.org/10.1016/S0031-6865(99)00010-2

[8]. Popp, F. D.; Parson, R.; Donigan, B. E. J. Heterocycl. Chem. 1980, 17, 1329-1330.
http://dx.doi.org/10.1002/jhet.5570170639

[9]. Pandeya, S. N.; Sriram, D.; DeClercq, E.; Nath, G. Eur. J. Pharm. Sci. 1999, 9, 25-31.
http://dx.doi.org/10.1016/S0928-0987(99)00038-X

[10]. Singh, G. S.; Singh, T.; Lakhan, R. Indian J. Chem. 1997, 36B, 951-954.

[11]. Bhattacharya, S. K.; Chakrabarti S. Indian J. Exp. Biol. 1998, 36, 118-121.
PMid:9536661

[12]. Sridhar. S. K.; Pandeya. S. N.; De Clercq, E. Boll. Chim. Farm. 2001, 140, 302-305.
PMid:11680082

[13]. El-Sawi. E. A.; Mostafa, T. B.; Mostafa, B. B. J. Egypt Soc. Parasitol. 1998, 28, 481-486.
PMid:9707676

[14]. Khan, K. M.; Mughal, U. R.; Samreen, P. S.; Choudhary, M. I. Lett. Drug Des. Discovery 2008, 5, 243-249.
http://dx.doi.org/10.2174/157018008784619915

[15]. Imran, M.; Alam, O.; Kaushik, D.; Khan, S. A. Indian J. Heterocycl. Chem. 2007, 16, 251-254.

[16]. Gonzalez, A.; Quirante, J.; Nieto, J.; Almeida, M. R.; Saraiva, M. J.; Arsequell, G.; Valancia, G. Bioorg. Med. Chem. Lett. 2009, 19, 5270-5273.
http://dx.doi.org/10.1016/j.bmcl.2009.03.004

[17]. Pandey, V. K.; Dwivedi, A.; Pandey, O. P.; Sengupta, S. K. J. Agric. Food Chem. 2008, 56, 10779-10784.
http://dx.doi.org/10.1021/jf801975z
PMid:18954075

[18]. Bekircan, O.; Bektas, H. Molecules 2008, 13, 2126-2135.
http://dx.doi.org/10.3390/molecules13092126
PMid:18830145

[19]. Turan-Zitouni, G.; Kaplancikli, Z. A.; Yildiz, M. T.; Chevallet, P.; Kaya, D. Eur. J. Med. Chem. 2005, 40, 607-613.
http://dx.doi.org/10.1016/j.ejmech.2005.01.007
PMid:15922844

[20]. Chen, J.; Sun, X. Y.; Chai, K. Y.; Lee, J. S.; Song, M. S.; Quan, Z. S. Bioorg. Med. Chem. 2007, 15, 6775-6781.
http://dx.doi.org/10.1016/j.bmc.2007.08.004

[21]. Bekircan, O.; Gumrukcuoglu, N. Indian J. Chem. 2005, 44B, 2107-2113.

[22]. Turan-Zitouni, G.; Kaplancikli, Z. A.; Erol, K.; Kilic, F. S. Farmaco 1999, 54, 218-223.
http://dx.doi.org/10.1016/S0014-827X(99)00016-6

[23]. Akhtar, T.; Hameed, S.; Al-Masoudi, N. A.; Khan, K. M. Heteroat. Chem. 2007, 18, 316-322.
http://dx.doi.org/10.1002/hc.20282

[24]. Turan-Zitouni, G.; Kaplancikli, Z. A.; Ozdemir, A.; Chevallet, P.; Kandilci, H. B.; Gamusel, B. Arch. Pharm. Chem. Life Sci 2007, 340, 586-590.
http://dx.doi.org/10.1002/ardp.200700134
PMid:17994651

[25]. Williams, D.; Fleming, I. Spectroscopic methods in organic chemistry, 2nd Ed. McGraw-Hill Book Company (UK), 1973.

[26]. Jawetz, E.; Melnick, J. L.; Adelberg, E. A. Review of Medica Microbiology, Lang Medical Publication, Los Altos, California 1974.

[27]. Grayer, R. J.; Harbone, J. B. Phytochem. 1994, 37, 19-42.
http://dx.doi.org/10.1016/0031-9422(94)85005-4

[28]. Muanza, D. N.; Kim, B. W.; Euler, L. L.; Williams, L. J. Pharmacol. 1994, 32, 337-345.

[29]. Irob, O. N.; Moo-Young, M.; Aperson, W. A. Inter. J. Pharmacol. 1996, 34, 87-90.

[30]. Varma, R. S.; Khan, I. A. J. Indian Chem. Soc. 1979, 56, 1038-1040.

[31]. Riisalu, H.; Vasilev, V. V.; Ionin, B. I. Zh. Obshch. Khim. 1984, 54, 563-569.

[32]. Riisalu H.; VasiIev V. V.; Ionin B. I. Zh. Obshch. Khim. 1985, 55, 2237-2243.

[33]. Sharma, D.; Bansal, R. K. J. Indian Chem. Soc. 1990, 67, 29-32.


Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


El-Sawi, E.; Mostafa, T.; Radwan, H. Eur. J. Chem. 2011, 2(4), 539-543. doi:10.5155/eurjchem.2.4.539-543.55
El-Sawi, E.; Mostafa, T.; Radwan, H. Synthesis and biological activity of functionalized phosphorus derivatives of isatin imines. Eur. J. Chem. 2011, 2(4), 539-543. doi:10.5155/eurjchem.2.4.539-543.55
El-Sawi, E., Mostafa, T., & Radwan, H. (2011). Synthesis and biological activity of functionalized phosphorus derivatives of isatin imines. European Journal of Chemistry, 2(4), 539-543. doi:10.5155/eurjchem.2.4.539-543.55
El-Sawi, Emtithal, Tahia Bayoumy Mostafa, & Hyam Ali Radwan. "Synthesis and biological activity of functionalized phosphorus derivatives of isatin imines." European Journal of Chemistry [Online], 2.4 (2011): 539-543. Web. 10 Dec. 2023
El-Sawi, Emtithal, Mostafa, Tahia, AND Radwan, Hyam. "Synthesis and biological activity of functionalized phosphorus derivatives of isatin imines" European Journal of Chemistry [Online], Volume 2 Number 4 (31 December 2011)

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.2.4.539-543.55


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 2011, 2(4), 539-543 | doi: https://doi.org/10.5155/eurjchem.2.4.539-543.55 | 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.