Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties

Hany Mahmoud Dalloul; Khaled A. El-nwairy; Ali Zayed Shorafa; Ahmed Sulyman Abu Samaha

doi:doi:10.11648/j.ajhc.20170301.11

| Peer-Reviewed

Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties

Hany Mahmoud Dalloul, Khaled A. El-nwairy, Ali Zayed Shorafa, Ahmed Sulyman Abu Samaha

Published in American Journal of Heterocyclic Chemistry (Volume 3, Issue 1)

Received: 28 October 2016 Accepted: 10 February 2017 Published: 1 March 2017

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

Abstract

A new series of 1,2,4,8-tetraazaspiro[4.5]dec-2-enes containing 1,2,4-triazole, piperidine and sulfonamide moieties have been synthesized from the reaction of 4-piperidone benzoylhydrazones having 1-methyl, 1-benzyl, and 1-isopropyl groups with appropriate nitrilimines. The microanalysis and spectral data (IR, ¹H NMR, ¹³C NMR and MS) of the synthesized compounds are in full agreement with their molecular structure. The microbial features of the synthesized compounds were studied by a known method. Some of titled compounds exhibited significant antimicrobial activity on several strains of microbes.

Published in	American Journal of Heterocyclic Chemistry (Volume 3, Issue 1)
DOI	10.11648/j.ajhc.20170301.11
Page(s)	1-7
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Nitrilimines, Piperidine, Sulfonamide, 1,2,4,8-tetraazaspiro[4.5]dec-2-ene

References

[1]	Sayed, A. R. Tetrahedron 2012, 68(13), 2784-2789.
[2]	Sayed, A. R.; Wiggins, J. S. J. Appl. Poly. Sci. 2011, 120(2), 623-630.
[3]	Sayed, A. R. Tetrahedron Lett. 2010, 51, 4490-4493.
[4]	Sayed, A. R.; Wiggins, J. S. Polymer 2008, 49(9), 2253-2259.
[5]	G. Periyasami, R. Raghunathan, G. Surendiran, N. Mathivanan, Eur. J. Med. Chem., 2009, 44, 959.
[6]	K. Amin, M. Kamel, M. Anwar, M. Khedr, Y. M. Syamb, Eur. J. Med. Chem., 2010, 45, 2117.
[7]	R. R. Kumar, S. Perumal, S. C. Manju, P. Bhatt, P. Yogeeswari and D. Sriram, Bioorg. Med. Chem. Lett., 2009, 19, 3461.
[8]	A. Dandia, R. Singh, S. Khaturia, C. Merienne, G. Morgant and A. Loupy, Bioorg. Med. Chem., 2006, 14, 2409.
[9]	G. Lang, A. Pinkert, J. W. Blunt and M. H. G. Munro, J. Nat. Prod., 2005, 68,1796.
[10]	C. A. Maier and B. Wuensch, J. Med. Chem., 2002, 45, 438.
[11]	M. Wolf, A. A. Masciffi, US Patent, 1968, 395, 156; Chem. Abstr., 1988, 69, 96504r.
[12]	H. C. Rohm, British Patent, 1962, 913, 937; Chem. Abstr. 1963, 59, 577f.
[13]	G. Winters and N. D. Mola, German Patent, 1975, 2442, 667; Chem. Abstr. 1975, 83, 28096.
[14]	M. J. Kornet and A. P. Thio, J. Med. Chem., 1976, 19, 892.
[15]	S. Gurvinder, Maninderjit K., Mohan C., Int Res J Pharm. 2013, 4, 82
[16]	H. C. Patil, Patil I. M., Brose S. L, Pawar S. P, World J Pharm Pharmaceut Sci. 2015, 4:532
[17]	P. B. Mohite, Bhaskar V. H, Int J PharmTech Res., 2011, 3, 1557
[18]	N. A. Kheder, S. M. Riyadh, A. M. Asiry, Chem. Pharm. Bull. 2013, 61 (5) 504–510.
[19]	Y. Naito, F. Akahoshi, S. Takeda, T. Okada, M. Kajii, H. Nishimura, M. Sugiura, C. Fukaya, Y. Kagitani, J. Med. Chem., 1996, 39, 3019.
[20]	K. Okonogi and A. Tasaka, Can. Pat. Appl. CA 2 132 791 (Chem. Abstr., 1996, 124, 8821t).
[21]	S. M. Kudari, S. M. Beede, W. Munera, Asian J. Chem., 1997, 9, 20.
[22]	T. Denzel and H. Hoehn, U. S. Patent 1976, 3 971 801 (Chem. Abstr., 1977, 86, P16675k).
[23]	A. H. El-Masry, H. H. Fahmy, S. H. Ali and A. S. Waheed, Molecules, 2000, 5, 1429.
[24]	A. S. Orabi, M. A. Moneim, E. E. Salem, M. E. Abdel-Fattah, Polish J. Chem., 2000, 74, 1675.
[25]	A. Almasirad, S. A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi and A. Shafiee, Bioorg. Med. Chem Lett., 2004, 14, 6057.
[26]	T. George, D. Mehta, R. Tahilramani, J. David, P. Talwalker, J. Med. Chem., 1971, 14, 335.
[27]	J. Bailey, J. Chem. Soc. Perkin Trans. 1, 1977, 2047.
[28]	T. Farghaly, M. Abdallah, G. Masaret, Z. Muhammad, Eur. J. Med. Chem., 2015, 97, 320.
[29]	N. Abdel Hafez, T. Farghaly, M. Al-Omar, M. Abdalla, Eur. J. Med. Chem., 2010, 45, 4838.
[30]	T. A. Farghaly and H. K. Mahmoud, Arch. Pharm. Chem. Life Sci., 2013, 346, 392.
[31]	Girgis, A. S., Barsoum, F. F., Samir, A. Eur. J. Med. Chem. 2009, 44, 2447-2451.
[32]	Dalloul, H. M. Arkivoc, 2008 (xiv) 234-241.
[33]	Dalloul, H. M.; Abu samaha, A. J Serb Chem. Soc., 2010, 75, 1473-1479.
[34]	Dalloul, H. M.; Boyle, P. H. Heterocycl. Commun. 2003, 9, 507-514.
[35]	Dalloul, H. M. Chem. Heterocycl. Comp. 2004, 40, 1402-1407.
[36]	Dalloul, H. M.; Boyle, P. H. Turk. J. Chem. 2006, 30, 119-124.
[37]	Dalloul, H. M.; Boyle, P. H. Heterocycl. Commun. 2007, 13, 155-160.
[38]	Thaher B. A.; Otto, H-H., Monatsh. Chem. 2002, 133, 1011-1016.
[39]	H. Hassaneen, Shawali, A., Elwan N., Abounada, N., Sulfur Lett. 1992, 13, 273-285.
[40]	H. Hassaneen, A. Shawali, N. Elwan, N. Abounada, Org. Prep. Proced. Int. 1992, 24,171-175.
[41]	H. Dalloul, K. El-nwairy, A. Shorafa A. Abu Samaha, South. Braz. J. Chem. 2016, Accepted.
[42]	M. Okimoto, T. Chiba, J. Org. Chem., 1990, 55, 1070.
[43]	H. M. Dalloul, South. Braz. J. Chem. 2015, 22, 17-26.
[44]	M. Hesse, H. Meier, B. Zech, Spectroscopic Methods in Organic Chemistry, George Thieme Verlag, Stuttgart, 1997, p. 229.

Cite This Article

Plain Text BibTeX RIS

APA Style

Hany Mahmoud Dalloul, Khaled A. El-nwairy, Ali Zayed Shorafa, Ahmed Sulyman Abu Samaha. (2017). Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties. American Journal of Heterocyclic Chemistry, 3(1), 1-7. https://doi.org/10.11648/j.ajhc.20170301.11

Copy | Download

ACS Style

Hany Mahmoud Dalloul; Khaled A. El-nwairy; Ali Zayed Shorafa; Ahmed Sulyman Abu Samaha. Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties. Am. J. Heterocycl. Chem. 2017, 3(1), 1-7. doi: 10.11648/j.ajhc.20170301.11

Copy | Download

AMA Style

Hany Mahmoud Dalloul, Khaled A. El-nwairy, Ali Zayed Shorafa, Ahmed Sulyman Abu Samaha. Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties. Am J Heterocycl Chem. 2017;3(1):1-7. doi: 10.11648/j.ajhc.20170301.11

Copy | Download

@article{10.11648/j.ajhc.20170301.11,
  author = {Hany Mahmoud Dalloul and Khaled A. El-nwairy and Ali Zayed Shorafa and Ahmed Sulyman Abu Samaha},
  title = {Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {3},
  number = {1},
  pages = {1-7},
  doi = {10.11648/j.ajhc.20170301.11},
  url = {https://doi.org/10.11648/j.ajhc.20170301.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20170301.11},
  abstract = {A new series of 1,2,4,8-tetraazaspiro[4.5]dec-2-enes containing 1,2,4-triazole, piperidine and sulfonamide moieties have been synthesized from the reaction of 4-piperidone benzoylhydrazones having 1-methyl, 1-benzyl, and 1-isopropyl groups with appropriate nitrilimines. The microanalysis and spectral data (IR, 1H NMR, 13C NMR and MS) of the synthesized compounds are in full agreement with their molecular structure. The microbial features of the synthesized compounds were studied by a known method. Some of titled compounds exhibited significant antimicrobial activity on several strains of microbes.},
 year = {2017}
}

Copy | Download

TY  - JOUR
T1  - Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties
AU  - Hany Mahmoud Dalloul
AU  - Khaled A. El-nwairy
AU  - Ali Zayed Shorafa
AU  - Ahmed Sulyman Abu Samaha
Y1  - 2017/03/01
PY  - 2017
N1  - https://doi.org/10.11648/j.ajhc.20170301.11
DO  - 10.11648/j.ajhc.20170301.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 1
EP  - 7
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20170301.11
AB  - A new series of 1,2,4,8-tetraazaspiro[4.5]dec-2-enes containing 1,2,4-triazole, piperidine and sulfonamide moieties have been synthesized from the reaction of 4-piperidone benzoylhydrazones having 1-methyl, 1-benzyl, and 1-isopropyl groups with appropriate nitrilimines. The microanalysis and spectral data (IR, 1H NMR, 13C NMR and MS) of the synthesized compounds are in full agreement with their molecular structure. The microbial features of the synthesized compounds were studied by a known method. Some of titled compounds exhibited significant antimicrobial activity on several strains of microbes.
VL  - 3
IS  - 1
ER  -

Copy | Download

Author Information

Hany Mahmoud Dalloul

Department of Chemistry, Faculty of Applied Science, Alaqsa University of Gaza, Gaza Strip, Palestine
Khaled A. El-nwairy

Ministry of Education & Higher Education, South Remal, Gaza, Palestine
Ali Zayed Shorafa

Ministry of Education & Higher Education, South Remal, Gaza, Palestine
Ahmed Sulyman Abu Samaha

Department of Biology, Faculty of Applied Science, Alaqsa University, Gaza, Palestine

Download PDF

Sections

Plain Text BibTeX RIS

APA Style

Hany Mahmoud Dalloul, Khaled A. El-nwairy, Ali Zayed Shorafa, Ahmed Sulyman Abu Samaha. (2017). Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties. American Journal of Heterocyclic Chemistry, 3(1), 1-7. https://doi.org/10.11648/j.ajhc.20170301.11

Copy | Download

ACS Style

Hany Mahmoud Dalloul; Khaled A. El-nwairy; Ali Zayed Shorafa; Ahmed Sulyman Abu Samaha. Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties. Am. J. Heterocycl. Chem. 2017, 3(1), 1-7. doi: 10.11648/j.ajhc.20170301.11

Copy | Download

AMA Style

Hany Mahmoud Dalloul, Khaled A. El-nwairy, Ali Zayed Shorafa, Ahmed Sulyman Abu Samaha. Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties. Am J Heterocycl Chem. 2017;3(1):1-7. doi: 10.11648/j.ajhc.20170301.11

Copy | Download

@article{10.11648/j.ajhc.20170301.11,
  author = {Hany Mahmoud Dalloul and Khaled A. El-nwairy and Ali Zayed Shorafa and Ahmed Sulyman Abu Samaha},
  title = {Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {3},
  number = {1},
  pages = {1-7},
  doi = {10.11648/j.ajhc.20170301.11},
  url = {https://doi.org/10.11648/j.ajhc.20170301.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20170301.11},
  abstract = {A new series of 1,2,4,8-tetraazaspiro[4.5]dec-2-enes containing 1,2,4-triazole, piperidine and sulfonamide moieties have been synthesized from the reaction of 4-piperidone benzoylhydrazones having 1-methyl, 1-benzyl, and 1-isopropyl groups with appropriate nitrilimines. The microanalysis and spectral data (IR, 1H NMR, 13C NMR and MS) of the synthesized compounds are in full agreement with their molecular structure. The microbial features of the synthesized compounds were studied by a known method. Some of titled compounds exhibited significant antimicrobial activity on several strains of microbes.},
 year = {2017}
}

Copy | Download

TY  - JOUR
T1  - Synthesis and Antimicrobial Activities Evaluation of New Spiro[4.5]dec-2-enes Containing 1,2,4-Triazole, Piperidine and Sulfonamide Moieties
AU  - Hany Mahmoud Dalloul
AU  - Khaled A. El-nwairy
AU  - Ali Zayed Shorafa
AU  - Ahmed Sulyman Abu Samaha
Y1  - 2017/03/01
PY  - 2017
N1  - https://doi.org/10.11648/j.ajhc.20170301.11
DO  - 10.11648/j.ajhc.20170301.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 1
EP  - 7
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20170301.11
AB  - A new series of 1,2,4,8-tetraazaspiro[4.5]dec-2-enes containing 1,2,4-triazole, piperidine and sulfonamide moieties have been synthesized from the reaction of 4-piperidone benzoylhydrazones having 1-methyl, 1-benzyl, and 1-isopropyl groups with appropriate nitrilimines. The microanalysis and spectral data (IR, 1H NMR, 13C NMR and MS) of the synthesized compounds are in full agreement with their molecular structure. The microbial features of the synthesized compounds were studied by a known method. Some of titled compounds exhibited significant antimicrobial activity on several strains of microbes.
VL  - 3
IS  - 1
ER  -

Copy | Download