European Journal of Chemistry 2011, 2(4), 514-518 | doi: https://doi.org/10.5155/eurjchem.2.4.514-518.479 | 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 reactions of 3-aminotetrachloroquinazolin-2,4-dione


Mamdouh Adly Hassan (1) , Ahmed Mohamed Mosalem Younes (2) , Mohamed Mobark Taha (3) , Abou-Bakr Haredy Abdel-Monsef (4,*)

(1) Chemistry Department, Faculty of Science, South Valley University, Qena-83523, Egypt
(2) Chemistry Department, Faculty of Science, South Valley University, Qena-83523, Egypt
(3) Chemistry Department, Faculty of Science, South Valley University, Qena-83523, Egypt
(4) Chemistry Department, Faculty of Science, South Valley University, Qena-83523, Egypt
(*) Corresponding Author

Received: 21 Jun 2011 | Accepted: 31 Jul 2011 | Published: 31 Dec 2011 | Issue Date: December 2011

Abstract


N-phenylsulphonyloxytetrachlorophthalimide was obtained by treatment of N-hydroxy tetrachlorophthalimide with benzenesulphonyl chloride. Also, the titled compound 3 was obtained by reaction of compound 2 with hydrazine hydrate via Lossen rearrangement. Compound 3 used as starting material for the synthesis of new pyrimidine and quinazolinedione derivatives containing four chlorine atoms which have pharmacological activity.

2_4_514_518_800


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Quinazolinedione; Hydrazine hydrate; Anti-inflammatory; Tetrachloroquinazolindione; N-Phenylsulphonyloxytetrachlorophthalimide; 3-(N-acetylamino)tetrachloroquinazolindione

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.2.4.514-518.479

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1282 times | icon graph PDF Article downloaded 584 times


Citations

/


[1]. Nader M. Boshta, Farag A. El-Essawy, Mohammed B. Alshammari, Safaa G. Noreldein, Osama M. Darwesh
Discovery of Quinazoline-2,4(1H,3H)-Dione Derivatives as Potential Antibacterial Agent: Design, Synthesis, and Their Antibacterial Activity
Molecules  27(12), 3853, 2022
DOI: 10.3390/molecules27123853
/


[2]. Huda R. M. Rashdan, Aboubakr H. Abdelmonsef, Mortaga M. Abou-Krisha, Tarek A. Yousef
Synthesis, Identification, Computer-Aided Docking Studies, and ADMET Prediction of Novel Benzimidazo-1,2,3-triazole Based Molecules as Potential Antimicrobial Agents
Molecules  26(23), 7119, 2021
DOI: 10.3390/molecules26237119
/


[3]. M. A. Hassan, A. M. M. Younes, M. M. Taha, A. Abdel-Monsef
Synthesis and Reactions of 3-(2-Chloromethyl-carbonylamino)tetrachloroquinazolin-2,4-dione
Organic Chemistry International  2012, 1, 2012
DOI: 10.1155/2012/284947
/


[4]. Eduardo Enciso, Juan I. Sarmiento-Sánchez, Héctor S. López-Moreno, Adrián Ochoa-Terán, Ulises Osuna-Martínez, Evangelina Beltrán-López
Synthesis of new quinazolin-2,4-diones as anti-Leishmania mexicana agents
Molecular Diversity  20(4), 821, 2016
DOI: 10.1007/s11030-016-9693-8
/


[5]. Lumadhar Santos-Ballardo, Fernando García-Páez, Lorenzo A Picos-Corrales, Adrián Ochoa-Terán, Pedro Bastidas, Loranda Calderón-Zamora, Guadalupe Rendón-Maldonado, Ulises Osuna-Martínez, Juan I Sarmiento-Sánchez
Synthesis, biological evaluation and molecular docking of 3-substituted quinazoline-2,4(1H, 3H)-diones
Journal of Chemical Sciences  132(1), , 2020
DOI: 10.1007/s12039-020-01813-1
/


[6]. Gülay Akyüz, Emre Menteşe
Synthesis and Characterization of New Bistriazole Quinazolinediones and their Urease Inhibition Activities
Letters in Organic Chemistry  20(3), 258, 2023
DOI: 10.2174/1570178619666220816121312
/


[7]. B. A. Selivanov, A. Y. Tikhonov, E. F. Belanov, N. I. Bormotov, A. S. Kabanov, O. Yu. Mazurkov, O. A. Serova, L. N. Shishkina, A. P. Agafonov, A. N. Sergeev
Synthesis and Antiviral Activity of 1-Aryl-3-(3,5-Dioxo-4-Azatetracyclo-[5.3.2.02,6.08,10]Dodec-11-EN-4-YL)Ureas
Pharmaceutical Chemistry Journal  51(6), 439, 2017
DOI: 10.1007/s11094-017-1629-9
/


[8]. Iwona E. Głowacka, Katarzyna Gawron, Dorota G. Piotrowska, Mirthe Graus, Graciela Andrei, Dominique Schols, Robert Snoeck, Anita Camps, Emiel Vanhulle, Kurt Vermeire
Design and synthesis of a new series of hybrids of functionalised N1-[(1H-1,2,3-triazol-4-yl)methyl]quinazoline-2,4-dione with antiviral activity against Respiratory Syncytial Virus
Antiviral Research  209, 105518, 2023
DOI: 10.1016/j.antiviral.2022.105518
/


[9]. Mamdouh Adly Hassan, Maghrabi Ali Seleem, Ahmed Mohamed Mosallem Younes, Mohamed Mobark Taha, Abou-Bakr Haredi Abdel-Monsef
Synthesis and spectral characterization of some heterocyclic nitrogen compounds
European Journal of Chemistry  4(2), 121, 2013
DOI: 10.5155/eurjchem.4.2.121-123.740
/


[10]. Aboubakr H. Abdelmonsef, Ahmed M. Mosallam
Synthesis, in vitro biological evaluation and in silico docking studies of new quinazolin‐2,4‐dione analogues as possible anticarcinoma agents
Journal of Heterocyclic Chemistry  57(4), 1637, 2020
DOI: 10.1002/jhet.3889
/


[11]. Aboubakr H. Abdelmonsef, Mohamed A. Abdelhakeem, Ahmed M. Mosallam, Hussain Temairk, Mohamed El‐Naggar, Hend Okasha, Huda R. M. Rashdan
A search for antiinflammatory therapies: Synthesis, in silico investigation of the mode of action, and in vitro analyses of new quinazolin‐2,4‐dione derivatives targeting phosphodiesterase‐4 enzyme
Journal of Heterocyclic Chemistry  59(3), 474, 2022
DOI: 10.1002/jhet.4395
/


[12]. Galal H. Elgemeie, Rasha A. Azzam, Rasha E. Elsayed
Sulfa drug analogs: new classes of N-sulfonyl aminated azines and their biological and preclinical importance in medicinal chemistry (2000–2018)
Medicinal Chemistry Research  28(8), 1099, 2019
DOI: 10.1007/s00044-019-02378-6
/


[13]. Ahmed M. Abo-Bakr, Hesham M. Alsoghier, Aboubakr H. Abdelmonsef
Molecular docking, modeling, semiempirical calculations studies and in vitro evaluation of new synthesized pyrimidin-imide derivatives
Journal of Molecular Structure  1249, 131548, 2022
DOI: 10.1016/j.molstruc.2021.131548
/


References


[1]. Agrawal, J. P.; Chouk M. P. Res. Ind. J. 1982, 27, 19-21.

[2]. Sou, S.; Mayumi, S.; Takahashi, H.; Yamasaki, R.; Kadoya, S.; Sodeoka, M.; Hashimoto, Y. Bioorg. Med. Chem. Lett. 2000, 10, 1081-1086.
http://dx.doi.org/10.1016/S0960-894X(00)00161-X

[3]. Valencia, R.; Mason M. J.; Woodruff C. R.; Zimmering, S. Environ. Mutagen. 1985, 7, 325-348.
http://dx.doi.org/10.1002/em.2860070309
PMid:3930234

[4]. Wenzel, D. G. J. Am. Pharm. Assoc. 1995, 44, 550-553.
http://dx.doi.org/10.1002/jps.3030440911

[5]. Hansen, P.; Pederesen, E. B. Acta Chem. Scand. 1990, 44, 522-523.
http://dx.doi.org/10.3891/acta.chem.scand.44-0522

[6]. Maillard, J.; Vincent M.; Benard, M. Chem. Ther. 1968, 3, 100-106.

[7]. Hong, E. U. S. Patent 3726979. Chem. Abstract. 1973, 79, 27560a.

[8]. Akgun, H.; Hollstein, U.; Hrwitz L. J. Pharm. Sci. 1988, 77, 735-739.
http://dx.doi.org/10.1002/jps.2600770902

[9]. Havera, H. J.; Vidiro H. J. Med. Chem. 1979, 22, 1548-1550.
http://dx.doi.org/10.1021/jm00198a024
PMid:231656

[10]. Havera H. J. Ger. Patent 242858, (1979). Chem. Abstract 1975, 82, 171029p.

[11]. Fahmy, A. F. M.; Youssef, M. S. K.; Abdel Halim, M. S.; Hassan M. A.; Saur, J. Heterocycles 1986, 24, 2201-2213.
http://dx.doi.org/10.3987/R-1986-08-2201

[12]. Fahmy, A. F. M.; Aly, N. F.; Nada A.; Aly N. Y. Bull. Chem. Soc. Jpn. 1977, 50, 2678-2681.
http://dx.doi.org/10.1246/bcsj.50.2678

[13]. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, John Wiley, 1916, 35.

[14]. Seeley, H. W.; VanDemank, P. J. Selected Exercises from Microbes in Action A laboratory Manual of Microbiology, 3rd Ed., W.H. Freeman & Co Ltd., 1981.

[15]. Ryan, K. J; Ray, C. G. Sherris Medical Microbiology (4th edn), McGraw Hill. ISBN 0-8385-8529-9, 2004.

[16]. Selassie, C. D.; Li, R.; Poe, M.; Hansch, C. J. Med. Chem. 1991, 34, 46-54.
http://dx.doi.org/10.1021/jm00105a008

[17]. Cheng, C. C. Prog. Med. Chem. 1969, 6, 67-134.
http://dx.doi.org/10.1016/S0079-6468(08)70197-8

[18]. Nair-Scott, D. B. M.; Ulbrich, T. L. V.; Rogers, M. L.; Chu, E.; Rose, C. Cancer Res. 1959, 19, 15-19.
PMid:13638986

[19]. Narla, R. K.; Myres, D. E. Clin. Cancer Res. 1998, 4, 1405-1414.
PMid:9626456


How to cite


Hassan, M.; Younes, A.; Taha, M.; Abdel-Monsef, A. Eur. J. Chem. 2011, 2(4), 514-518. doi:10.5155/eurjchem.2.4.514-518.479
Hassan, M.; Younes, A.; Taha, M.; Abdel-Monsef, A. Synthesis and reactions of 3-aminotetrachloroquinazolin-2,4-dione. Eur. J. Chem. 2011, 2(4), 514-518. doi:10.5155/eurjchem.2.4.514-518.479
Hassan, M., Younes, A., Taha, M., & Abdel-Monsef, A. (2011). Synthesis and reactions of 3-aminotetrachloroquinazolin-2,4-dione. European Journal of Chemistry, 2(4), 514-518. doi:10.5155/eurjchem.2.4.514-518.479
Hassan, Mamdouh, Ahmed Mohamed Mosalem Younes, Mohamed Mobark Taha, & Abou-Bakr Haredy Abdel-Monsef. "Synthesis and reactions of 3-aminotetrachloroquinazolin-2,4-dione." European Journal of Chemistry [Online], 2.4 (2011): 514-518. Web. 3 Jun. 2023
Hassan, Mamdouh, Younes, Ahmed, Taha, Mohamed, AND Abdel-Monsef, Abou-Bakr. "Synthesis and reactions of 3-aminotetrachloroquinazolin-2,4-dione" 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.2.4.514-518.479


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), 514-518 | doi: https://doi.org/10.5155/eurjchem.2.4.514-518.479 | 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.