Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities

Abdelmotaal Abdelmajeid; Mahasen Saad Amine; Reda Ali Hassan

doi:doi:10.11648/j.ajhc.20180402.11

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Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities

Abdelmotaal Abdelmajeid, Mahasen Saad Amine, Reda Ali Hassan

Published in American Journal of Heterocyclic Chemistry (Volume 4, Issue 2)

Received: 12 March 2018 Accepted: 11 April 2018 Published: 3 July 2018

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Abstract

Acryloylphenylstearamide (2) was utilized as a starting material for synthesis the titled compounds via one-pot synthesis. Compound (2) was reacted with hydroxylamine hydrochloride in pyridine and produced isooxazole (3), and with thiosemicarbazide in pyridine and/or hydrazine-hydrate in ethanol afforded pyrazoles (4), and (5), while the reaction of (2) with urea and/ or thiourea in an alcoholic solution of sodium ethoxide gave pyrimidinone (6) and pyrimidinedione (7). Also, reaction of (2) with acetylacetone and/or ethyl acetoacetate in acetic acid andammonium acetateafforded Pyridine derivatives (8), and (9) respectively. Addition of different amounts of propylene oxide (3, 5, 7 moles) to the synthesized compounds produced nonionic surfactants (2-9a-c). The physiochemical and surface active properties of the prepared surfactant as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. Also, the surface parameters as effectiveness (πCMC), efficiency (PC20), maximum surface excess (Γmax) and (Amin) were evaluated.

Published in	American Journal of Heterocyclic Chemistry (Volume 4, Issue 2)
DOI	10.11648/j.ajhc.20180402.11
Page(s)	30-41
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), 2018. Published by Science Publishing Group

Keywords

Stearoyl Chloride, P-Aminoacetophenone, Nonionic Surfactant, Propylene Oxide

References

[1]	Abdelmajeid, A., Amine, M. S. and Hassan, R. A. (2017) Fatty Acids in Heterocyclic Synthesis. Part XVI Synthesis of Non-Ionic Surfactants Containing Piperidine, Piperazine, Imidazole Based on Thiadiazole and Evaluation of the Microbiological Activities. International Journal of Organic Chemistry, 7, 346-368. https://doi.org/10.4236/ijoc.2017.74029.
[2]	Iman A. G. Karim, Mahasen S. Amine, Amal A. Mahmoud, Alaa S. Gouda. J. Surfact. Deterg. (2014) 17:509-523. Fatty acids in heterocyclic synthesis. Part XIV; synthesis of surface active agents from some novel class of oxadiazole, thiadiazole and triazole derivatives having microbiological activities.
[3]	Amine, M. S., Eissa, A. M. F., Elsawy, A. A, Shaaban, A. F., El said, R. Grasas Aceites. (2004) New heterocycles having a double character as antimicrobial and surface active agents. Part1: nonionic compounds from fatty acid isothiocyanate. 55, 370-376.
[4]	Amine, M. S., Mahmoud, A. A., Badr, S. K., Gouda, A. S. (2011) Fatty acids in heterocyclic synthesis. Part XIII: 2-chloro-5-heptadecyl[1, 3, 4]thiadiazole as a building block for the synthesis of S-triazolo[2, 4-b]thiadiazole, benzimidazo[2, l-b]thiadiazole, thiadiazolo[2, 3-b]quinazolin-5-one as well as thiadiazol-2-yl (piperidine, pyridazine and/or phthalazine) Olaj, Szappan, Kozmetika, 60, 51-57.
[5]	Amine, M. S., Mahmoud, A. A., Badr, S. K., Gouda, A. S. (2013) Fatty Acids in Heterocyclic Synthesis. Part XI: Facile and Convenient Routes to Synthesize Eco-friendly Polyfunctionalized Thiadiazoles, Triazole, Thiadiazolo [3, 2-a] pyrimidines and Imidazo[2, 1-b]thiadiazole for Pharmaceutical and Industrial Purposes. Egypt. J. Chem. 56 (5), 379-401.
[6]	Amine, M. S., Mahmoud, A. A., Badr, S. K., Gouda, A. S. (2012) Fatty acids in heterocyclic synthesis part xii: synthesis of surfactants from pyrazole, isoxazole, pyrimidine, and triazine, incorporating the 1, 3, 4-thiadiazole moiety having dyeing and antimicrobial activities J. Surf. Deterg. 15, 179-190.
[7]	Amine, M. S., Ahmed, M. H. M., Hebash, K. A., and El-Sheikh, A. A. (2010) Utilization of stearic in heterocyclic synthesis Part 8: synthesis of some new thiadiazoles and triazoles of industrial application. Olaj, Szappan, Kozmetika, 59, 30-34.
[8]	Amine, M. S., Ahmed, M. H. M., Hebash, K. A., El-Sheikh, A. A. (2007) New heterocycles having a double character as antimicrobial and surface active agents. Part 6: novel thiadiazole from stearic acid. OLAJ, Szappan, Kozmetika, 56, 57-61.
[9]	Hanahan, D. and J. Folkman. (1996). Patterns and emerging mechanisms of the angiogenic switch during tumorigenesis. Cell 86: 353-364.
[10]	Sumitani, K., R. Kamijo, T. Toyoshima, Y. Nakanishi, K. Takizawa, M. Hatori, and M. Nagumo. (2001). Specific inhibition of cyclooxygenase-2 results in inhibition of proliferation of oral cancer cell lines via suppression of prostaglandin E2 production. Journal of Oral Pathology & Medicine 30: 41-47.
[11]	Ding, X. Z., C. A. Kuszynski, T. H. El-Metwally, and T. E. Adrian. (1999). Lipoxygenase inhibition induced apoptosis, morphological changes, and carbonic anhydrase expression in human pancreatic cancer cells. Biochemical and biophysical ResearchCommunications 266: 392-399.
[12]	Ding, X. Z., W. G. Tong, and T. E. Adrian. (2001). 12-lipoxygenase metabolite12 (S) HETE stimulates human pancreatic cancer cell proliferation via protein tyrosine phosphorylation and ERK activation. International J. of Cancer J. International Du Cancer 94: 630-636.
[13]	Form, D. M., and R. Auerbach. (1983). PGE2 and angiogenesis, F. et al. (2009) The discovery of the potent Aurora inhibitor M. Proceedings of the Society for Experimental Biology and Medicine 172: 214-218.
[14]	Chahrour, O., Cairns, D., Omran, Z. (2012) Small molecule kinase inhibitors as anti-cancer therapeutics. Mini-Rev. Med. Chem. 5, 399-411.
[15]	Bebbington, D., Binch, H., Charrier, J.-D., Everitt, S., Fraysse, D., Golec, J., Kay, D., Knegtel, R., Mak, C., Mazzei K-0457 (VX-680). Bioorg. Med. Chem. Lett. 19, 3586-3592.
[16]	Fletcher, G. C., Brokx, R. D., Denny, T. A., Hembrough, T. A., Plum, S. M., Fogler, W. E., Sidor, C. F., Bray, M. R. (2011) ENMD-2076 is an orally active kinase inhibitor with antiangiogenic and antiproliferative mechanisms of action. Mol. Cancer Ther. 1, 126-137.
[17]	Mortlock, A. A., Foote, K. M., Heron, N. M., Jung, F. H., Pasquet, G., Lohmann, J. J., Warin, N., Renaud, F., de Savi, C., Roberts, N. J., et al (2007) Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of Aurora B kinase. J. Med. Chem. 9, 2213-2224.
[18]	Kumar A, Sinha S, Chauhan PM. (2012) Synthesis of novel antimycobacterial combinatorial libraries of structural diverse substituted pyrimidines by three-component solid phase reactions. Bioorg Med Chem Lett.12, 667-669.
[19]	Baraldi, P. G, Pavani, M. G, Nunez, M, et al. (2002) Antimicrobial and antitumor activity of N-heteroimine-1, 2, 3-dithiazole and their transformation in triazole- imidazo- and pyrazolopyrimidines. Bioorg Med Chem. 10, 449-456.
[20]	Hanan, E. J., Fucini, R. V., Romanowski, M. J., Elling, R. A., Lew, W., Purkey, H. E., Vanderporten, E. C., and Yang, W. (2008). Design and synthesis of 2-amino-isoxazolopyridines as Polo-like kinase inhibitors. Bioorg. Med. Chem. Lett. 18, 5186-5189.
[21]	Mohamed, S. F., Youssef, M. M., Amr, A. E., Kotb, E. R. (2008). Antimicrobial activities of some synthesized pyridines, oxazines, and thiazoles from 3-aryl-1- (2-naphthyl) prop-2-en-1-ones. Sci. Pharm. 76:279-303.
[22]	Morgos J, Sallay P, Farkas L, Rusznak I (1983) A novel way for ethoxylation with the basic catalyst. J Am Oil Chem Soc 60:1905-1907.
[23]	Ahmed M. H. M, Sallay P, Rusznak I, Farkas L (1996) Determination of the average ethoxylation degree. Tenside Surf Deterg 33:410-411.
[24]	Findlay A (1963) Practical physical chemistry, 6th edn. Longmans, London, pp 1040-1069.
[25]	Weil JK, Stirton AJ, Nunez-Ponzoa MV (1966) Ether alcohol sulfates. The effect of oxypropylation and oxybutylation on surface active properties. J Am Oil Soc 43:603-609.
[26]	ASTM D1331-01 (2001) Standard Test method for surface and interfacial tension of solutions of surface active agents.
[27]	Durham K (1961) Properties of detergent solutions-amphipathyand adsorption, vol 1. Surf Activity Deterg. MacMillan &Co. Ltd., London, pp 1-28.
[28]	Draves CZ, Clarkson R (1931) A new method for the evaluation of wetting agents. J Am Dye Stuff Report 20:201.
[29]	Ross J, Milles GD (1941) Apparatus for comparison of foaming properties of soaps and detergents. Oil Soap 18:99-102.
[30]	Scholnick F, Linfield WM (1977) Lactose-derived surfactants (III): fatty esters of oxyalkylated lactitol. J Am Oil Chem Soc 54:430-435.
[31]	Colwell CE, Rixon WE (1961) Consideration in the use of nonionicsurface-active agents. Am Dyest Re 50:679-682.
[32]	Lu JR, Lee EM, Thomas RK, Penfold J, Flitsch SL (1993) Direct determination by neutron reflection of the structure of triethylene oxide monododecyl ether layers at the air/water interface. Langmuir 9:1352-1358.
[33]	Matsuoka K, Moroi Y (2003) Micellization of fluorinated amphiphiles. Curr Opin Colloids Interface Sci 8:227-234.
[34]	Zhigang Xu, Li Pengfei, Qi Weihong, Li Zongshi, Lubo Ch (2006) Effect of aromatic ring in the alkyl chain on surface properties of aryl alkyl surfactant solution. J Surf Deterg 9:245-248.
[35]	Karakashev SI, Nguyen AV, Miller JD (2008) Equilibrium adsorption of surfactants at the gas-liquid interface. Adv Polymer Sci 218:25-55.
[36]	Karakashev SI, Manev ED (2002) Effect of interactions betweenthe adsorbed species on the properties of single and mixed surfactantmonolayers at air/water interface. J Colloid Interface Sci 248:477-486.
[37]	Falbe J (1986) Surfactants for consumer, Chap 4. Springer Verlag, Heidelberg.

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APA Style

Abdelmotaal Abdelmajeid, Mahasen Saad Amine, Reda Ali Hassan. (2018). Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities. American Journal of Heterocyclic Chemistry, 4(2), 30-41. https://doi.org/10.11648/j.ajhc.20180402.11

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ACS Style

Abdelmotaal Abdelmajeid; Mahasen Saad Amine; Reda Ali Hassan. Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities. Am. J. Heterocycl. Chem. 2018, 4(2), 30-41. doi: 10.11648/j.ajhc.20180402.11

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AMA Style

Abdelmotaal Abdelmajeid, Mahasen Saad Amine, Reda Ali Hassan. Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities. Am J Heterocycl Chem. 2018;4(2):30-41. doi: 10.11648/j.ajhc.20180402.11

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@article{10.11648/j.ajhc.20180402.11,
  author = {Abdelmotaal Abdelmajeid and Mahasen Saad Amine and Reda Ali Hassan},
  title = {Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {4},
  number = {2},
  pages = {30-41},
  doi = {10.11648/j.ajhc.20180402.11},
  url = {https://doi.org/10.11648/j.ajhc.20180402.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20180402.11},
  abstract = {Acryloylphenylstearamide (2) was utilized as a starting material for synthesis the titled compounds via one-pot synthesis. Compound (2) was reacted with hydroxylamine hydrochloride in pyridine and produced isooxazole (3), and with thiosemicarbazide in pyridine and/or hydrazine-hydrate in ethanol afforded pyrazoles (4), and (5), while the reaction of (2) with urea and/ or thiourea in an alcoholic solution of sodium ethoxide gave pyrimidinone (6) and pyrimidinedione (7). Also, reaction of (2) with acetylacetone and/or ethyl acetoacetate in acetic acid andammonium acetateafforded Pyridine derivatives (8), and (9) respectively. Addition of different amounts of propylene oxide (3, 5, 7 moles) to the synthesized compounds produced nonionic surfactants (2-9a-c). The physiochemical and surface active properties of the prepared surfactant as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. Also, the surface parameters as effectiveness (πCMC), efficiency (PC20), maximum surface excess (Γmax) and (Amin) were evaluated.},
 year = {2018}
}

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TY  - JOUR
T1  - Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities
AU  - Abdelmotaal Abdelmajeid
AU  - Mahasen Saad Amine
AU  - Reda Ali Hassan
Y1  - 2018/07/03
PY  - 2018
N1  - https://doi.org/10.11648/j.ajhc.20180402.11
DO  - 10.11648/j.ajhc.20180402.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 30
EP  - 41
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20180402.11
AB  - Acryloylphenylstearamide (2) was utilized as a starting material for synthesis the titled compounds via one-pot synthesis. Compound (2) was reacted with hydroxylamine hydrochloride in pyridine and produced isooxazole (3), and with thiosemicarbazide in pyridine and/or hydrazine-hydrate in ethanol afforded pyrazoles (4), and (5), while the reaction of (2) with urea and/ or thiourea in an alcoholic solution of sodium ethoxide gave pyrimidinone (6) and pyrimidinedione (7). Also, reaction of (2) with acetylacetone and/or ethyl acetoacetate in acetic acid andammonium acetateafforded Pyridine derivatives (8), and (9) respectively. Addition of different amounts of propylene oxide (3, 5, 7 moles) to the synthesized compounds produced nonionic surfactants (2-9a-c). The physiochemical and surface active properties of the prepared surfactant as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. Also, the surface parameters as effectiveness (πCMC), efficiency (PC20), maximum surface excess (Γmax) and (Amin) were evaluated.
VL  - 4
IS  - 2
ER  -

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Author Information

Abdelmotaal Abdelmajeid

Chemistry Department, Faculty of Science, Benha University, Benha, Egypt
Mahasen Saad Amine

Chemistry Department, Faculty of Science, Benha University, Benha, Egypt
Reda Ali Hassan

Chemistry Department, Faculty of Science, Benha University, Benha, Egypt

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Abdelmotaal Abdelmajeid, Mahasen Saad Amine, Reda Ali Hassan. (2018). Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities. American Journal of Heterocyclic Chemistry, 4(2), 30-41. https://doi.org/10.11648/j.ajhc.20180402.11

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ACS Style

Abdelmotaal Abdelmajeid; Mahasen Saad Amine; Reda Ali Hassan. Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities. Am. J. Heterocycl. Chem. 2018, 4(2), 30-41. doi: 10.11648/j.ajhc.20180402.11

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AMA Style

Abdelmotaal Abdelmajeid, Mahasen Saad Amine, Reda Ali Hassan. Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities. Am J Heterocycl Chem. 2018;4(2):30-41. doi: 10.11648/j.ajhc.20180402.11

Copy | Download

@article{10.11648/j.ajhc.20180402.11,
  author = {Abdelmotaal Abdelmajeid and Mahasen Saad Amine and Reda Ali Hassan},
  title = {Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {4},
  number = {2},
  pages = {30-41},
  doi = {10.11648/j.ajhc.20180402.11},
  url = {https://doi.org/10.11648/j.ajhc.20180402.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20180402.11},
  abstract = {Acryloylphenylstearamide (2) was utilized as a starting material for synthesis the titled compounds via one-pot synthesis. Compound (2) was reacted with hydroxylamine hydrochloride in pyridine and produced isooxazole (3), and with thiosemicarbazide in pyridine and/or hydrazine-hydrate in ethanol afforded pyrazoles (4), and (5), while the reaction of (2) with urea and/ or thiourea in an alcoholic solution of sodium ethoxide gave pyrimidinone (6) and pyrimidinedione (7). Also, reaction of (2) with acetylacetone and/or ethyl acetoacetate in acetic acid andammonium acetateafforded Pyridine derivatives (8), and (9) respectively. Addition of different amounts of propylene oxide (3, 5, 7 moles) to the synthesized compounds produced nonionic surfactants (2-9a-c). The physiochemical and surface active properties of the prepared surfactant as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. Also, the surface parameters as effectiveness (πCMC), efficiency (PC20), maximum surface excess (Γmax) and (Amin) were evaluated.},
 year = {2018}
}

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TY  - JOUR
T1  - Fatty Acids in Heterocyclic Synthesis: Part XIX Synthesis of Some Isoxazole, Pyrazole, Pyrimidine and Pyridine and Their Surface, Anticancer and Antioxidant Activities
AU  - Abdelmotaal Abdelmajeid
AU  - Mahasen Saad Amine
AU  - Reda Ali Hassan
Y1  - 2018/07/03
PY  - 2018
N1  - https://doi.org/10.11648/j.ajhc.20180402.11
DO  - 10.11648/j.ajhc.20180402.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 30
EP  - 41
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20180402.11
AB  - Acryloylphenylstearamide (2) was utilized as a starting material for synthesis the titled compounds via one-pot synthesis. Compound (2) was reacted with hydroxylamine hydrochloride in pyridine and produced isooxazole (3), and with thiosemicarbazide in pyridine and/or hydrazine-hydrate in ethanol afforded pyrazoles (4), and (5), while the reaction of (2) with urea and/ or thiourea in an alcoholic solution of sodium ethoxide gave pyrimidinone (6) and pyrimidinedione (7). Also, reaction of (2) with acetylacetone and/or ethyl acetoacetate in acetic acid andammonium acetateafforded Pyridine derivatives (8), and (9) respectively. Addition of different amounts of propylene oxide (3, 5, 7 moles) to the synthesized compounds produced nonionic surfactants (2-9a-c). The physiochemical and surface active properties of the prepared surfactant as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. Also, the surface parameters as effectiveness (πCMC), efficiency (PC20), maximum surface excess (Γmax) and (Amin) were evaluated.
VL  - 4
IS  - 2
ER  -

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