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1,2,3-Thiadiazolyl Isocyanates in the Synthesis of Biologically Active Compounds. Study of the Cytotoxic Activity of N-(4-methyl-1,2,3-thiadi-azolyl-5-yl)-N'-(4-methylphenyl)Urea*

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Chemistry of Heterocyclic Compounds Aims and scope

A simple method is proposed for the synthesis of 1,2,3-thiadiazolylureas by the reaction of 1,2,3-thia-diazolyl isocyanates with primary amines. 1,2,3-Thiadiazolyl isocyanates were obtained in situ by the Curtius rearrangement of 1,2,3-thiadiazolylcarbonyl azides. Cytokinin activity was tested for N-(4-methyl-1,2,3-thiadiazol-5-yl)-N'-(4-methylphenyl)urea, which is an analog of thidiazuron, differing in the presence of two methyl groups in the molecule.

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This work was carried out with the financial support of the Russian Foundation for Basic Research (grant 13-03-00137 A).

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Authors and Affiliations

  1. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    T. A. Kalinina, Yu. S. Shakhmina, T. V. Glukhareva, Yu. Yu. Morzherin, R. A. Borzenkova, E. S. Skolobanova & I. S. Kiseleva

  2. State Heteroorganic Chemistry Laboratory, Nankai University, 94 Weijin Road, Tianjin, 30071, China

    Z.-J. Fan

Authors
  1. T. A. Kalinina
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  2. Yu. S. Shakhmina
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  3. T. V. Glukhareva
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  4. Yu. Yu. Morzherin
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  5. Z.-J. Fan
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  6. R. A. Borzenkova
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  7. E. S. Skolobanova
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  8. I. S. Kiseleva
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Correspondence to Yu. Yu. Morzherin.

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*Dedicated to Academician O. N. Chupakhin on the occasion of his 80th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1127-1134, July, 2014.

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Kalinina, T.A., Shakhmina, Y.S., Glukhareva, T.V. et al. 1,2,3-Thiadiazolyl Isocyanates in the Synthesis of Biologically Active Compounds. Study of the Cytotoxic Activity of N-(4-methyl-1,2,3-thiadi-azolyl-5-yl)-N'-(4-methylphenyl)Urea*. Chem Heterocycl Comp 50, 1039–1046 (2014). https://doi.org/10.1007/s10593-014-1561-9

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  • DOI: https://doi.org/10.1007/s10593-014-1561-9

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