Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents

Mahmoud Mohamed Abdelall

doi:doi:10.11648/j.ajhc.20170302.11

| Peer-Reviewed

Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents

Mahmoud Mohamed Abdelall

Published in American Journal of Heterocyclic Chemistry (Volume 3, Issue 2)

Received: 15 April 2017 Accepted: 10 May 2017 Published: 5 June 2017

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

Abstract

A new series of heterocycles incorporating antipyrine moiety were synthesized via reactions of 4-aminoantipyrine 1 with carbon disulphide then alkylation and /or chloroacetic acid to produce dithiocarbamate and rhodanine 3, 4 and 9. Multi-component reaction (MCR) of 4-aminoantipyrine with carbon disulfide and DMAD afforded rhodanine 7. The interaction of 9 with diazonium salt, DMF-DMA, nitrous acid and aromatic aldehydes to give thiazolidinone derivatives 10, 11, 13 and 14, respectively. Pyranothiazole 16 was prepared from reaction of 9 with cinamonitrile 15. Thiazolidinone 18 and thiazole 19 derivatives were obtained from reactions of 9 with phenyl isothiocyanate in the presence of KOH then halogenated the pot salt with ethyl bromoacetate and chloroacetone, respectively. Thiourea derivative 20 was prepared from reaction of methyl dithiocarbamate 3 with 4-aminoantipyrine. pyrimidine derivatives 21 and 22 were obtained from cyclocondensation of 3 with dimer of ethyl cyanoacetate and malononitrile. Pyrazolotriazine 24 was prepared from interaction of 3 with hydrazine hydrate. copounds 26 and 28 were obtained via reaction of 3 with glycine and anthranilic acid. Compounds 30, 32 and 34 were prepared via reaction of thiourea 20 with EAA, ECA and DMAD. Reaction of diazonium chloride of 1 with NaN3 afforded azide 36 which rearranged to triazine 39. The structures of the newly synthesized compounds were elucidated via elemental analysis and spectral data. The synthesized products were evaluated for their antimicrobial and anti-fungal activity.

Published in	American Journal of Heterocyclic Chemistry (Volume 3, Issue 2)
DOI	10.11648/j.ajhc.20170302.11
Page(s)	8-18
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

Antipyrine, Rhodanine, Thiazole, Pyranothiazole, Antimicrobial Activity

References

[1]	V. C. Filho, R. Correa, Z. Vaz, J. B. Calixto, R. J. Nunes, T. R. Pinheiro, A. D. Andricopulo, R. A. Yunes, Farmaco 53 (1998) 55.
[2]	S. M. Sondhi, V. K. Sharma, R. P. Verma, N. Singhal, R. Shukla, R. Raghubir, M.P. Dubey, Synthesis (1999) 878.
[3]	M. M. F. Ismail, Y. A. Ammar, H. S. A. El-Zahaby, S. I. Eisa, S. E. Barakat, Arch. Pharm. Life Sci. 340 (2007) 476.
[4]	A. P. Mishra, J. Indian Chem. Soc. 76 (1999) 35.
[5]	N. Raman, A. Kulandaisamy, K. Jeyasubramanian, Synth. React. Inorg. Met. 32 (2002) 1583.
[6]	N. Raman, A. Kulandaisamy, K. Jeyasubramanian, Synth. React. Inorg. Met. 34 (2004) 17.
[7]	S. M. Sondhi, N. Singhal, R. P. Verma, S. K. Arora, S. G. Dastidar, Indian J. Chem., Sect .B, 40 (2001) 113.
[8]	M. A. Madiha, A. Rania, H. Moataz, S. Samira, B. Sanaa, Eur. J. Pharmacol. 569(2007) 222.
[9]	A. N. Evstropov, V. E. Yavorovskaya, E. S. Vorob, Z. P. Khudonogova, L. N. Gritsenko, E. V. Shmidt, S. G. Medvedeva, V. D. Filimonov, T. P. Prishchep, A. S. Saratikov, Pharm. Chem. J. 26 (1992) 426.
[10]	McCrea, J. B.; Vlasses, P.H.; Rocci, M. L., Jr. Ann Pharmacother 23( 1989) 38.
[11]	Meffin, P. J.; Williams, R. L.; Blaschke, T. F.; Rowland, M. J Pharm Sci, 66(1977) 135.
[12]	Wensing, G.; Neumann, U.; Ohnhaus, E. E.; Heidemann, H. T. Clini Pharmacother, 48(1990) 575.
[13]	M. Yu, M. Kanji, I. Hitoshi, H. Chitoshi, O. Satoru, and S. Takashi, Chemical & Pharmaceutical Bulletin, vol. 39, no. 6 (1991) 1440– 1445.
[14]	J. H. Ahn, S. J. Kim, W. S. Park et al., Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 11 (2006) 2996.
[15]	M. Sortino, P. Delgado, S. Juarez et al., Bioorganic and Medicinal Chemistry, vol. 15, no. 1 (2007) 484.
[16]	T. S. Wan, L. L. Cheng, L. Y. Su, P. L. Siew, and M. S. Mui, Bioorganic & Medicinal Chemistry Letters, vol. 11 (2001) 91.
[17]	Ming-Xia Song, Chang-Ji Zheng, Xian-Qing Deng, Zhi-Yu Wei and Hu-Ri Piao j. medicinal chemistry, 4(5) (2014) 441.
[18]	Wael A. A. Arafa, Mervat F. Fareed, Saleh A. Rabeh & Raafat M. Shaker, phosphorus, sulfur, and silicon, 191(8) (216)1129.
[19]	V. Alagarsamy and P. Parthiban J. Heterocyclic Chem., 51, (2014)1615.
[20]	M Gobinath1, N Subramanian, V Alagarsamy, S Nivedhitha and V Raja Solomon, Trop J Pharm Res, February; 14(2) (2015)271.
[21]	M. Gobinath, N. Subramanian, K. Ruckmani, V. Alagarsamy, International Journal of Drug Design and Discovery,2(4) (2011)642.
[22]	M. Abdalla Hussein, International Journal of Applied Biology and Pharmaceutical Technology, 1(3) (2010)1054.
[23]	Hong-Jian Zhang, Peng Jin, Shi-Ben Wang, Fu-Nan Li, Li-Ping Guan, and Zhe-Shan Quan, Arch. Pharm. Chem. Life Sci. 348 (2015) 564.
[24]	Aly, H. M.; El-Gazzar, M. G. Arzneimittelforschung, 62 (2012)105.
[25]	A. Reiser, H. Wagner, and G. Bowes, Tetrahedron Lett.,7(23) (1966) 2635 .
[26]	A. Reiser, G. Bowes, and R. J. Horne, Trans. Faraday SOC., 62 (1966) 3162.
[27]	A. Reiser, H. M. Wagner, R. Marley, and G. Bowes, Trans. Faraday SOC, 63 (1967)2403.
[28]	L. Horner and A. Christmann, Angew. Chem., 75,707(1963); Angew.Clem. Int.Ed. Engl., 2(1963)599.
[29]	G. Labbe Chem. Rev., 69 (3) (1969)345.
[30]	P. A. S. Smith, L. 0. Krbechek, AND W. Resemann, Journal of the American Chemical Society, 86 (1964)2025.
[31]	N. Svenstrup, K. B. Simonsen, N. Thorup, J. Brodersen, W. Dehaen, and J. Becher, J. Org. Chem., 64 (1999) 2814.
[32]	Bauer, A. W., Kirby, W. W. M., Sherris, J. C., and Turck, M., American Journal of Clinical Pathology, 45 (1966) 493.

Cite This Article

Plain Text BibTeX RIS

APA Style

Mahmoud Mohamed Abdelall. (2017). Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents. American Journal of Heterocyclic Chemistry, 3(2), 8-18. https://doi.org/10.11648/j.ajhc.20170302.11

Copy | Download

ACS Style

Mahmoud Mohamed Abdelall. Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents. Am. J. Heterocycl. Chem. 2017, 3(2), 8-18. doi: 10.11648/j.ajhc.20170302.11

Copy | Download

AMA Style

Mahmoud Mohamed Abdelall. Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents. Am J Heterocycl Chem. 2017;3(2):8-18. doi: 10.11648/j.ajhc.20170302.11

Copy | Download

@article{10.11648/j.ajhc.20170302.11,
  author = {Mahmoud Mohamed Abdelall},
  title = {Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {3},
  number = {2},
  pages = {8-18},
  doi = {10.11648/j.ajhc.20170302.11},
  url = {https://doi.org/10.11648/j.ajhc.20170302.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20170302.11},
  abstract = {A new series of heterocycles incorporating antipyrine moiety were synthesized via reactions of 4-aminoantipyrine 1 with carbon disulphide then alkylation and /or chloroacetic acid to produce dithiocarbamate and rhodanine 3, 4 and 9. Multi-component reaction (MCR) of 4-aminoantipyrine with carbon disulfide and DMAD afforded rhodanine 7. The interaction of 9 with diazonium salt, DMF-DMA, nitrous acid and aromatic aldehydes to give thiazolidinone derivatives 10, 11, 13 and 14, respectively. Pyranothiazole 16 was prepared from reaction of 9 with cinamonitrile 15. Thiazolidinone 18 and thiazole 19 derivatives were obtained from reactions of 9 with phenyl isothiocyanate in the presence of KOH then halogenated the pot salt with ethyl bromoacetate and chloroacetone, respectively. Thiourea derivative 20 was prepared from reaction of methyl dithiocarbamate 3 with 4-aminoantipyrine. pyrimidine derivatives 21 and 22 were obtained from cyclocondensation of 3 with dimer of ethyl cyanoacetate and malononitrile. Pyrazolotriazine 24 was prepared from interaction of 3 with hydrazine hydrate. copounds 26 and 28 were obtained via reaction of 3 with glycine and anthranilic acid. Compounds 30, 32 and 34 were prepared via reaction of thiourea 20 with EAA, ECA and DMAD. Reaction of diazonium chloride of 1 with NaN3 afforded azide 36 which rearranged to triazine 39. The structures of the newly synthesized compounds were elucidated via elemental analysis and spectral data. The synthesized products were evaluated for their antimicrobial and anti-fungal activity.},
 year = {2017}
}

Copy | Download

TY - JOUR
T1 - Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents
AU - Mahmoud Mohamed Abdelall
Y1 - 2017/06/05
PY - 2017
N1 - https://doi.org/10.11648/j.ajhc.20170302.11
DO - 10.11648/j.ajhc.20170302.11
T2 - American Journal of Heterocyclic Chemistry
JF - American Journal of Heterocyclic Chemistry
JO - American Journal of Heterocyclic Chemistry
SP - 8
EP - 18
PB - Science Publishing Group
SN - 2575-5722
UR - https://doi.org/10.11648/j.ajhc.20170302.11
AB - A new series of heterocycles incorporating antipyrine moiety were synthesized via reactions of 4-aminoantipyrine 1 with carbon disulphide then alkylation and /or chloroacetic acid to produce dithiocarbamate and rhodanine 3, 4 and 9. Multi-component reaction (MCR) of 4-aminoantipyrine with carbon disulfide and DMAD afforded rhodanine 7. The interaction of 9 with diazonium salt, DMF-DMA, nitrous acid and aromatic aldehydes to give thiazolidinone derivatives 10, 11, 13 and 14, respectively. Pyranothiazole 16 was prepared from reaction of 9 with cinamonitrile 15. Thiazolidinone 18 and thiazole 19 derivatives were obtained from reactions of 9 with phenyl isothiocyanate in the presence of KOH then halogenated the pot salt with ethyl bromoacetate and chloroacetone, respectively. Thiourea derivative 20 was prepared from reaction of methyl dithiocarbamate 3 with 4-aminoantipyrine. pyrimidine derivatives 21 and 22 were obtained from cyclocondensation of 3 with dimer of ethyl cyanoacetate and malononitrile. Pyrazolotriazine 24 was prepared from interaction of 3 with hydrazine hydrate. copounds 26 and 28 were obtained via reaction of 3 with glycine and anthranilic acid. Compounds 30, 32 and 34 were prepared via reaction of thiourea 20 with EAA, ECA and DMAD. Reaction of diazonium chloride of 1 with NaN3 afforded azide 36 which rearranged to triazine 39. The structures of the newly synthesized compounds were elucidated via elemental analysis and spectral data. The synthesized products were evaluated for their antimicrobial and anti-fungal activity.
VL - 3
IS - 2
ER -

Copy | Download

Author Information

Mahmoud Mohamed Abdelall

Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt; Chemistry Department, Faculty of Science and Art, Al-Baha University, Al-Baha, Saudi Arabia

Download PDF

Sections

Plain Text BibTeX RIS

APA Style

Mahmoud Mohamed Abdelall. (2017). Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents. American Journal of Heterocyclic Chemistry, 3(2), 8-18. https://doi.org/10.11648/j.ajhc.20170302.11

Copy | Download

ACS Style

Mahmoud Mohamed Abdelall. Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents. Am. J. Heterocycl. Chem. 2017, 3(2), 8-18. doi: 10.11648/j.ajhc.20170302.11

Copy | Download

AMA Style

Mahmoud Mohamed Abdelall. Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents. Am J Heterocycl Chem. 2017;3(2):8-18. doi: 10.11648/j.ajhc.20170302.11

Copy | Download

@article{10.11648/j.ajhc.20170302.11,
  author = {Mahmoud Mohamed Abdelall},
  title = {Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {3},
  number = {2},
  pages = {8-18},
  doi = {10.11648/j.ajhc.20170302.11},
  url = {https://doi.org/10.11648/j.ajhc.20170302.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20170302.11},
  abstract = {A new series of heterocycles incorporating antipyrine moiety were synthesized via reactions of 4-aminoantipyrine 1 with carbon disulphide then alkylation and /or chloroacetic acid to produce dithiocarbamate and rhodanine 3, 4 and 9. Multi-component reaction (MCR) of 4-aminoantipyrine with carbon disulfide and DMAD afforded rhodanine 7. The interaction of 9 with diazonium salt, DMF-DMA, nitrous acid and aromatic aldehydes to give thiazolidinone derivatives 10, 11, 13 and 14, respectively. Pyranothiazole 16 was prepared from reaction of 9 with cinamonitrile 15. Thiazolidinone 18 and thiazole 19 derivatives were obtained from reactions of 9 with phenyl isothiocyanate in the presence of KOH then halogenated the pot salt with ethyl bromoacetate and chloroacetone, respectively. Thiourea derivative 20 was prepared from reaction of methyl dithiocarbamate 3 with 4-aminoantipyrine. pyrimidine derivatives 21 and 22 were obtained from cyclocondensation of 3 with dimer of ethyl cyanoacetate and malononitrile. Pyrazolotriazine 24 was prepared from interaction of 3 with hydrazine hydrate. copounds 26 and 28 were obtained via reaction of 3 with glycine and anthranilic acid. Compounds 30, 32 and 34 were prepared via reaction of thiourea 20 with EAA, ECA and DMAD. Reaction of diazonium chloride of 1 with NaN3 afforded azide 36 which rearranged to triazine 39. The structures of the newly synthesized compounds were elucidated via elemental analysis and spectral data. The synthesized products were evaluated for their antimicrobial and anti-fungal activity.},
 year = {2017}
}

Copy | Download