Skip to main content
SpringerLink
Log in

Synthesis of Biodegradable Pyrazole, Pyran, Pyrrole, Pyrimidine and Chromene Derivatives having Medical and Surface Activities

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

In this research, stearic acid and propylene oxide are used to synthesize biodegradable heterocyles (pyrazole, pyran, chromene, and pyrimidine) to improve their solubility and lower their toxicity. The chemical structure of these surfactants was confirmed using IR, 1H, and 13C NMR spectra. Some of these compounds have higher activity than commercial antibiotics and may be useful in the pharmaceutical industry.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5

Similar content being viewed by others

References

  1. Zaghloul EK, Khadija MA, Ebtisam AH, Mohamed HE (2002) Enaminones in heterocyclic synthesis: a novel route to polyfunctionalized substituted thiophene, 2,3-dihydro-1,3,4-thiadiazole and naphtho[1,2-b]furan derivatives. Phosphorus Sulfur 177:105–114

    Article  Google Scholar 

  2. Zeba NS, Nayeem A, Farheen F, Kulsum K (2013) Highly efficient solvent-free synthesis of novel pyranyl pyridine derivatives via β-enaminones using ZnO nanoparticles. Tetrahedron Lett 54(28):3599–3604

    Article  Google Scholar 

  3. Ahmed AH (2014) Heterocyclic synthesis via enaminones: synthesis and molecular docking studies of some novel heterocyclic compounds containing sulfonamide moiety. Int J Org Chem 4:68–81

    Article  Google Scholar 

  4. Nouria AA, Maher RI, Mohamed HE, Elizabeth J, Yehia AI (2012) Enaminones in a multicomponent synthesis of 4-aryldihydropyridines for potential applications in photo induced intramolecular electron-transfer systems. Beilstein J Org Chem 8:441–447

    Article  Google Scholar 

  5. Silvio C, Lourenço LB (2014) Synthesis of quinolinediones by catalyst-free formal aza-[3 + 2+1] cycloaddition of enaminones, aldehydes and meldrum’s acid. J Braz Chem Soc 25(7):1311–1316

    Google Scholar 

  6. Mahmoud MA (2014) Synthesis of 1,3,4-thiadiazoles, α-pyranone, pyridine, polysubstituted benzene from 1, 3, 4-thiadiazolyl ethanone and testing against tuberculosis based on molecular docking studies. Orient J Chem 30(3):1099–1109

    Article  Google Scholar 

  7. Jehane IE, Aliaa RM, Nahed AH, Amal ME, Magda MN, Mohamed A (2014) In vivo antioxidant and antigenotoxic evaluation of an enaminone derivative BDHQ combined with praziquantel in uninfected and Schistosoma mansoni infected mice. J Appl Pharm Sci. 4(05):025–033

    Google Scholar 

  8. Viktor OI, Satenik M, Ashot G, Mariia M, Alexander V, Dmytro V, Vyacheslav YS, Peter L (2012) 2, 3-Unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines. Org Biomol Chem 10:890–894

    Article  Google Scholar 

  9. Riyadh SM (2011) Enaminones as building blocks for the synthesis of substituted pyrazoles with antitumor and antimicrobial activities. Molecules 16:1834–1853

    Article  CAS  Google Scholar 

  10. Riyadh SM, Abdelhamid IA, Al-Matar HM, Hilmy NM, Elnagdi MH (2008) Enamines as precursors to polyfunctional heteroaromatic compounds; a decade of development. Heterocycles 75:1849–1905

    Article  CAS  Google Scholar 

  11. Heikhshoaie I, Fabian WMF (2009) Theoretical insights into material properties of Schiff bases and related azo compounds. Curr Org Chem 13:149–171

    Article  Google Scholar 

  12. El-Apasery MA, Al-Mousawi SM, Mahmoud H, Elnagdi MH (2011) Novel routes to biologically active enaminones, dienoic acid amides, arylazonicotinates and dihydro-pyridazines under microwave irradiation. Int Res J Pure Appl Chem 1(3):69–83

    Article  CAS  Google Scholar 

  13. Oddeti G, Bhagavathula SD, Yellajyosula LNM (2012) A brief review on synthesis and applications of β-enamino carbonyl compounds. Org Commun 5(3):105–119

    Google Scholar 

  14. Kateb AA, Abd El-Rahman NM, Saleh TS, Ali MH, Elhaddad AS, El-Dosoky AY (2012) Microwave mediated facile synthesis of some novel pyrazole, pyrimidine, pyrazolo[1,5-a]pyrimidine, triazolo[1,5-a]pyrimidine and pyrimido[1,2-a]benzimidazole derivatives under solvent less condition. Nat Sci 10(11):77–86

    Google Scholar 

  15. Oshinori T, Hiroto O, Shinya K, Hisako M (2009) Reaction of enaminones with carbon disulfide: synthesis of heterocycles using enamino dithiocarboxylates. J Heterocycl Chem 28(5):1245–1255

    Google Scholar 

  16. Hanadi YM, Abdellatif MS (2014) Enamines in heterocyclic synthesis: route to amino-pyrazolo pyrimidines and arylpyrazolopyrimidiens derivatives. Mod Chem 2(1):1–5

    Article  Google Scholar 

  17. Fadda AA, Amine MS, Areif MMH, Kh Farahat E (2014) Novel synthesis, antimicrobial evaluation and reactivity of dihydroacetic acid with N, C-nucleophiles. Pharmacologia 5:1–11

    Article  Google Scholar 

  18. Kibou Z, Cheikh N, Choukchou-Braham N, Mostefakara B, Benabdellah M, Villemin D (2011) New methodology for the synthesis of 2-pyridones using basic Al2O3 as catalyst. J Mater Environ Sci 2(3):293–298

    CAS  Google Scholar 

  19. Himani V, Aiman A, Abdul R, Fohad MH, Iqbal A (2014) Synthesis and antimicrobial evaluation of fatty chain substituted 2,5-dimethyl pyrrole and 1,3-benzoxazin-4-one derivatives. J Saudi Chem Soc 26:290–299

    Google Scholar 

  20. Jubie S, Ramesh PN, Dhanabal P, Kalirajan R, Muruganantham N, Antony AS (2012) Synthesis, antidepressant and antimicrobial activities of some novel stearic acid analogues. Eur J Med Chem 54:931–935

    Article  CAS  Google Scholar 

  21. Khan AA, Alam M, Tufail S, Mustafa J, Owais M (2011) Synthesis and characterization of novel PUFA esters exhibiting potential anticancer activities: an in vitro study. Eur J Med Chem 46:4878–4886

    Article  CAS  Google Scholar 

  22. Xu LL, Zheng CJ, Sun LP, Miao J, Piao HR (2012) Synthesis of novel 1,3-diaryl pyrazole derivatives bearing rhodanine-3-fatty acid moieties as potential antibacterial agents. Eur J Med Chem 48:174–178

    Article  CAS  Google Scholar 

  23. Dongqing Xu, Qi Banghua, Di F, Xuemei Z, Ting Z (2016) Preparation, characterization and properties of novel cationic gemini surfactants with rigid amido spacer groups. J Surfact Deterg 19:91–99

    Article  Google Scholar 

  24. Vinayika S, Rashmi T (2016) Surface and aggregation properties of synthesized cetyl alcohol based bis-sulfosuccinate gemini surfactants in aqueous solution. J Surfact Deterg 19:111–118

    Article  Google Scholar 

  25. Wiesław H, Karolina D, Arkadiusz C, Agata S, Katarzyna M (2016) 2-Ethylhexanol derivatives as nonionic surfactants: synthesis and properties. J Surfact Deterg 19:155–164

    Article  Google Scholar 

  26. Farshori NN, Banday MR, Ahmad A, Khan AU, Rauf A (2011) 7-Hydroxycoumarin derivatives: synthesis, characterization and preliminary antimicrobial activities. Med Chem Res 20:535–541

    Article  CAS  Google Scholar 

  27. Varshney H, Ahmad A, Farshori NN, Ahmad A, Khan AU, Rauf A (2013) Synthesis and evaluation of in vitro antimicrobial activity of novel 2,3-disubstituted-4-thiazolidinones from fatty acid hydrazides. Med Chem Res 22:3204–3212

    Article  CAS  Google Scholar 

  28. El-Sayed R, Khairou SK (2015) Propoxylated fatty thiazole, pyrazole, triazole, and pyrrole derivatives with antimicrobial and surface activity. J Surfact Deterg 18:661–673

    Article  CAS  Google Scholar 

  29. El-Sayed R (2013) Substituted thiadiazole, oxadiazole, triazole and triazinone as antimicrobial and surface activity compounds. J Surfact Deterg 16(1):39–47

    Article  CAS  Google Scholar 

  30. El-Sayed R, Amani S, Al Mazrouee L (2015) Synthesis and evaluation of polyfunctionally substituted heterocyclic compounds derived from 2-cyano-n-(5-pentadecyl-1,3,4-thiadiazol-2-yl)acetamide. Synth Commun 1(45):886–897

    Article  Google Scholar 

  31. El-Sayed R, Asghar BH (2014) Synthesis of various nitrogen heterocycles as antimicrobial surface agents. J Heterocycl Chem 51:1245–1251

    Article  Google Scholar 

  32. Morgo´s J, Sallay P, Farkas L, Ruszna´k I (1986) A new approach of ethoxylation catalyzed by bridge head nitrogen containing compounds. J Am Oil Chem Soc 63:1209–1210

    Article  Google Scholar 

  33. Carrod LP, Grady FD (1972) Antibiotic and chemotherapy, 3rd edn. Churchill Livingstone, Edinburgh

    Google Scholar 

  34. Coffen DL, Korzan DG (1971) Synthetic quinine analogs. III. Frangomeric and anchimeric processes in the preparation and reactions of α, β-epoxy ketones. J Org Chem 36:390–395

    Article  CAS  Google Scholar 

  35. Findlay A (1963) Practical physical chemistry, 6th edn. Longmans, London, pp 1039–1040

    Google Scholar 

  36. 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

    Article  CAS  Google Scholar 

  37. ASTM D1331-01 (2001) Standard Test method for surface and interfacial tension of solutions of surface active agents

  38. Durham K (1961) Properties of detergent solutions-amphipathy and adsorption. Surf activity deterg, vol 1. MacMillan, London, pp 1–28

    Google Scholar 

  39. Draves CZ, Clarkson R (1931) A new method for the evaluation of wetting agents. J Am Dye Stuff Rep 20:201

    CAS  Google Scholar 

  40. Ross J, Milles GD (1941) Apparatus for comparison of foaming properties of soaps and detergents. Oil Soap 18:99–102

    Article  CAS  Google Scholar 

  41. Eter ET, Richard RE, Darid A (1974) Biodegradable surfactants derived from corn starch. J Am Oil Chem Soc 51:486–494

    Article  Google Scholar 

  42. Falbe J (1986) Surfactants for consumer, chap 4. Springer, Heidelberg

    Google Scholar 

  43. Ghodile NG, Rajput PR (2014) Synthesis and characterization of some new n, o and s containing chlorosubstituted heterocycles and their antimicrobial screening against some common causative organisms. Int J Innov Res Sci Eng Technol 3(4):373–377

    Google Scholar 

  44. El-Sayed R (2008) Surface active properties and biological activity of novel nonionic surfactants containing pyrimidines and related nitrogen heterocyclic ring systems. Grasas Aceites 59(2):110–120

    Article  CAS  Google Scholar 

  45. Samir B, Abd El-Gaber T, Fadda AA (2011) Behavior of 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)-acrylamide towards some nitrogen nucleophiles. Arkivoc 2:227–239

    Google Scholar 

  46. Laurier LS, Elaine NS, Gerrard DM (2003) Surfactants and their applications. Annu Rep Prog Chem Sect C 99:3–48

    Google Scholar 

  47. Somaya EA, Eissa AEMF, Ahmed MN (2015) Synthesis, physicochemical properties and biological evaluation of some peptide candidates by use of liquid phase method as potential antimicrobial and surface active agents. Int J Pharm 11(7):726–731

    Article  Google Scholar 

  48. Ismail T (2013) Evaluation of some non-ionic surfactants prepared from olive oil having antiseptic activity. 3rd International Conference on Medical, Biological and Pharmaceutical Sciences (ICMBPS’2013) January 4–5, Bali (Indonesia)

Download references

Acknowledgments

The authors are greatly appreciative to the staff of the Microbiology Department, Faculty of Science, Umm Al-Qura University for facilitating in carrying out the antibacterial investigation for the newly synthesized compounds.

Author information

Authors and Affiliations

  1. Chemistry Department, College of Applied Sciences, Umm Al-Qura University, Makkah, 21955, Saudi Arabia

    Refat El-Sayed

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

    Refat El-Sayed

Authors
  1. Refat El-Sayed
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Refat El-Sayed.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

El-Sayed, R. Synthesis of Biodegradable Pyrazole, Pyran, Pyrrole, Pyrimidine and Chromene Derivatives having Medical and Surface Activities. J Surfact Deterg 19, 1153–1167 (2016). https://doi.org/10.1007/s11743-016-1881-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-016-1881-0

Keywords

Search

Navigation