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Site-selective reactions of hydrazonoyl chlorides with cyanoacetic hydrazide and its N-arylidene derivatives and anti-aggressive activity of prepared products

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Abstract

Reactions of hydrazonoyl halides with cyanoacetic hydrazide and its N-arylidene derivatives proceeded site-selectively and afforded the respective pyrazolo[3,4-d]pyridazine and aldehyde N-(1-aryl-3-acetyl-4-cyanopyrazol-5-yl)hydrazone derivatives. The structures of the products were elucidated on the basis of their spectral and elemental analyses. The anti-aggressive activity of the compounds prepared was screened.

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References

  • Al-Awadi, N., M.H. Elnagdi, T. Mathew, I. El-Gamr, and M. Andel-Khalik. 1996. Pyrolysis of aminonitriles, cyanohydrazones, and cyanoacetamides. Part I. Elimination reaction of 1-arylmethyleneamino-1,2-dihydro-4,6-dimethyl-2-oxopyridine-3-carbonitriles and substituted benzaldehyde cyanoacetylhydrazones. International Journal of Chemical Kinetics 28: 741–748.

    Article  CAS  Google Scholar 

  • Awad, B.M., A.R.S. Ferwanah, A.M. Awadallah, and N.M. El-Halabi. 2002. Reaction of nitrilimines with keto-alkoxycarbonyl-hydrazones: Synthesis of substituted 1,2,4-triazoles and heterocyclic spiro compounds. Asian Journal of Chemistry 14: 1235–1240.

    CAS  Google Scholar 

  • Awadallah, A.M., E.A. El-Sawi, A.R.S. Ferwanah, and H.M. Dalloul. 2002. 1,2,4- Triazoles from 1,3-dipolar cycloaddition reaction of nitrilimines with aliphatic ketohydrazones carrying electron withdrawing groups. Asian Journal of Chemistry 14: 1230–1234.

    CAS  Google Scholar 

  • Awadallah, A.M., A.R.S. Ferwanah, M.R. El-Haddad, and W. Schrader. 2004. Synthesis of substituted 1,2,4-triazoles from reaction of nitrilimines with substituted hydrazones. Asian Journal of Chemistry 16: 1691.

    CAS  Google Scholar 

  • Brady, J.V., and W.J.H. Nauta. 1953. Subcortical mechanisms in emotional behavior: Affective changes following septal forebrain lesions in the albino rat. Journal of Comparative and Physiological Psychology 46: 339–346.

    Article  PubMed  CAS  Google Scholar 

  • Duffin, G.F., and J.D. Kendall. 1960. British Patent, 850,976; 1961. Chemical Abstracts, 55, p10161e.

  • Geissler, G., M. Hippius, and G. Tomaschewski. 1982. Umsetzung von α-cyano-β-aryl-acrylsäure-ethylestern mit hydrazin, eine retro-Knoevenagel-reaktion. Journal für praktische Chemie 324: 910–914.

    Article  CAS  Google Scholar 

  • Guetzoyan, L.J., R.A. Spooner, J.M. Lord, L.M. Roberts, and G.J. Clarkson. 2010. Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of shiga toxin trafficking. European Journal of Medicinal Chemistry 45: 275–283.

    Article  PubMed  CAS  Google Scholar 

  • Heise, G.A., and E. Boff. 1961. Taming action of chlordiazepoxide. Federation Proceedings 20: 393–397.

    Google Scholar 

  • Horiuchi, T., M. Nagata, M. Kitagawa, K. Akahane, and Kouichi Uoto. 2009. Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of cyclin D1-CDK4: Synthesis, biological evaluation and structure-activity relationships. Part 2. Bioorganic & Medicinal Chemistry 17: 7850–7860.

    Article  CAS  Google Scholar 

  • Irwin, S., R. Kinohi, M. Van Sloten, and M.P. Workman. 1971. Drug effects on distress-evoked behavior in mice: methodology and drug class comparisons. Psychopharmacologia (Berl.) 20: 172–185.

    Article  CAS  Google Scholar 

  • Liu, W.Y., H.Y. Li, B.X. Zhao, D.S. Shin, S. Lian, and J.Y. Miao. 2009. Synthesis of novel ribavirin hydrazone derivatives and anti-proliferative activity against A549 lung cancer cells. Carbohydrate Research 344: 1270–1275.

    Article  PubMed  CAS  Google Scholar 

  • Randall, L.O., G.A. Heise, W. Schalleck, R.E. Bagdon, R. Banziger, A. Boris, A. Moe, and W.B. Abrams. 1961. Pharmacological and clinical studies on Valium(T.M.). A new psychotherapeutic agent of the benzodiazepine class. Current Therapeutic Research 9: 405–425.

    Google Scholar 

  • Rollas, S., and S.G. Kucukguzel. 2007. Biological activities of hydrazone derivatives. Molecules 12: 1910–1939.

    Article  PubMed  CAS  Google Scholar 

  • , A.S., and M.A. Abdallah. 1995. The chemistry of heterocyclic hydrazonoyl halides. Advances in Heterocyclic Chemistry 63: 277–338.

    Article  CAS  Google Scholar 

  • Shawali, A.S., and M.M. Edrees. 2006. Reactions of nitrilimines with heterocyclic amines and enamines. Convenient methodology for synthesis and annulation of heterocycles. Arkivoc ix: 292–365.

    Google Scholar 

  • Shawali, A.S., and S.M. Elsheikh. 2001. Annelated[1,2,4,5]tetrazines. Journal of Heterocyclic Chemistry 38: 541–559.

    Article  CAS  Google Scholar 

  • Shawali, A.S., and T.A. Farghaly. 2008. Reactions of hydrazonoyl halides with heterocyclic thiones. Convenient methodology for heteroannulation, synthesis of spiroheterocycles and heterocyclic ring transformation. Arkivoc i: 18–64.

    Article  Google Scholar 

  • Shawali, A.S., and M.A.N. Mosselhi. 2003. Hydrazonoyl halides: Useful building blocks for the synthesis of arylazoheterocycles. Journal of Heterocyclic Chemistry 40: 725–746.

    Article  CAS  Google Scholar 

  • Shawali, A.S., and C. Parkanyi. 1980. Hydrazidoyl halides in the synthesis of heterocycles. Journal of Heterocyclic Chemistry 17: 833–854.

    Article  CAS  Google Scholar 

  • Shawali, A.S. 1993. Reactions of heterocyclic compounds with nitrilimines and their precursors. Chemical Reviews 93: 1777–2731.

    Article  Google Scholar 

  • Shawali, A.S. 1983. Reactions of hydrazidoyl halides with sulfur compounds. Heterocycles 20: 2239–2285.

    Article  CAS  Google Scholar 

  • Shawali, A.S., and N.A. Samy. 2009. Hydrazonoyl halides: Their versatile biological activities. The Open Bioactive Compounds Journal 2: 8–16.

    Article  CAS  Google Scholar 

  • Shawali, A.S., and S.M. Sherif. 2007. The chemistry of hydrazonates. Current Organic Chemistry 11: 773–799.

    Article  CAS  Google Scholar 

  • Shawali, A.S. 2010a. Hydrazonoyl halides: A bubbling fountain of biologically active compounds. Current Organic Chemistry 14: 784–815.

    Article  CAS  Google Scholar 

  • Shawali, A.S. 2010b. Synthesis and tautomerism of aryl- and hetaryl-azo derivatives of bi- and tri-heterocycles. Journal of Advanced Research 1: 255–290.

    Article  Google Scholar 

  • Shawali, A.S. 2010c. Tandem in situ generation and 1,5-electrocyclization of N-hetaryl nitrilimines. A facile methodology for synthesis of annulated 1,2,4-triazoles and their acyclo C-nucleosides. Arkivoc I: 33–97.

    Google Scholar 

  • Xia, Y., C.D. Fan, B.X. Zhao, J. Zhao, D.S. Shin, and J.Y. Miao. 2008. Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells. European Journal of Medicinal Chemistry 43: 2347–2353.

    Article  PubMed  CAS  Google Scholar 

  • Zheng, L.W., L.L. Wu, B.X. Zhao, W.L. Dong, and J.Y. Miao. 2009. Synthesis of novel substituted pyrazole-5-carbohydrazide hydrazone derivatives and discovery of a potent apoptosis inducer in A549 lung cancer cells. Bioorganic & Medicinal Chemistry 17: 1957–1962.

    Article  CAS  Google Scholar 

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Correspondence to Ahmad Sami Shawali.

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Shawali, A.S., Farghaly, T.A., Hussein, S.M. et al. Site-selective reactions of hydrazonoyl chlorides with cyanoacetic hydrazide and its N-arylidene derivatives and anti-aggressive activity of prepared products. Arch. Pharm. Res. 36, 694–701 (2013). https://doi.org/10.1007/s12272-013-0082-x

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