RECENT PROGRESS IN THE SYNTHESIS OF bis-TRIAZENES

Department ($Chemistry, Saint M u p ' s University, Halifax, Nova Scoria, CANADA, B3H 3C3 INTRODUCTION ................................................................................................................................ 6 I I . Triazene Synthesis ...................................... 2. Antiturnour Activin ..... 3. Structure ............................................................................................................................. 62 4. Cyclic Triazenes ................................................................................................................. 62 5. Triazene Precursors of Heterocyclic Systenis I. bis3-(ARYLTRIAZEN-l-YL)ETHANES .................

[1]  K. Biradha,et al.  Crystal structure of 1,3-di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine , 1999 .

[2]  K. Biradha,et al.  Crystal structures of a series of 3,8-di[-2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes , 1999 .

[3]  K. Biradha,et al.  Crystal structures of a series of 3,7-bis-(arylazo)-1,3,5,7-tetraazabicyclo[3.3.1]nonanes , 1998 .

[4]  K. Vaughan,et al.  Synthesis and Characterization of Novel Bis-Triazenes: 3,8-Di[2-aryl-1-azenyl]-1,3,6,8-tetraazabicyclo[4.4.1]undecanes and 1,3-Di-2-[(4-methoxyphenyl)-1-diazenyl]imidazolidine. The Reaction of Diazonium Ions with Ethylenediamine/Formaldehyde Mixtures. , 1998, The Journal of organic chemistry.

[5]  C. Michejda,et al.  Triazinines: Synthesis and Proteolytic Decomposition of a New Class of Cyclic Triazenes , 1997 .

[6]  Jason V. Jollimore,et al.  1-Aryl-3-(carbamoylmethyl)triazenes: Synthesis, Spectroscopic Analysis and Cyclization to New 1,2,3-Benzotriazines , 1996 .

[7]  C. Michejda,et al.  Bistriazenes: multifunctional alkylating agents , 1991 .

[8]  R. Singer,et al.  Open chain nitrogen compounds. Part XI. 3,7-Bis(arylazo)-1,3,5,7-tetraazabicyclo[3,3,1]nonanes: the reaction of diazonium ions with ammonia–formaldehyde mixtures , 1986 .

[9]  K. Vaughan,et al.  Triazene metabolism. V. Chemical and biological properties of N,N-bis-[(1-aryl-3-methyltriazen-3-yl)-methyl]-methylamines: potential prodrugs for the cytotoxic monomethyltriazenes. , 1985, Anti-cancer drug design.

[10]  C. Schwalbe,et al.  Crystal and molecular structure of 3-methyl-1-p-tolyltriazene , 1984 .

[11]  S. Luner,et al.  Triazene metabolism. III. In vitro cytotoxicity towards M21 cells and in vivo antitumour activity of the proposed metabolites of the antitumour 1-aryl-3,3-dimethyltriazenes. , 1984, Canadian journal of physiology and pharmacology.

[12]  C. Hemens,et al.  Open-chain nitrogen compounds. Part VI. The formation of bis(1-aryl-3- methyltriazen-3-ylmethyl) methylamines in the reaction of diazonium ions with mixtures of formaldehyde and methylamine , 1984 .

[13]  J. Hickman,et al.  Studies of the mode of action of antitumor triazenes and triazines. 6. 1-Aryl-3-(hydroxymethyl)-3-methyltriazenes: synthesis, chemistry, and antitumor properties. , 1984, Journal of medicinal chemistry.

[14]  S. Carter,et al.  5-(3,3-dimethyl-l-triazeno)-imidazole-4-carboxamide (DTIC, DIC, NSC-45388)--a new antitumor agent with activity against malignant melanoma. , 1972, European journal of cancer.

[15]  R. Preussmann,et al.  Mechanism of carcinogenesis with 1-aryl-3,3-dialkyltriazenes. II. In vitro-alkylation of guanosine, RNA and DNA with aryl-monoalkyltriazenes to form 7-alkylguanine. , 1970, Biochemical pharmacology.

[16]  H. Böhme,et al.  ber Darstellung und Eigenschaften a-Halogenierter Amine , 1957 .

[17]  C. Stock,et al.  Triazenes as Inhibitors of Mouse Sarcoma 180.∗ , 1955, Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine.

[18]  M. Eble,et al.  Über die Tautomerie der Diazoaminoverbindungen , 1907 .

[19]  M. Zaworotko,et al.  Crystal structures of two 1,2-bis-(1-aryl-3-methyltriazene-3-yl-)ethanes with aryl substituents of opposite polarity , 1998 .

[20]  I. Pottie,et al.  1,2-Bis(1-aryl-3-alkyltriazen-3-yl)ethanes and related compounds , 1998 .

[21]  E S Newlands,et al.  Temozolomide: a review of its discovery, chemical properties, pre-clinical development and clinical trials. , 1997, Cancer treatment reviews.

[22]  K. Vaughan.  Triazenes: Synthesis and Chemical Properties , 1990 .

[23]  K. Vaughan,et al.  N,N-bis-(1-aryl-3-methyltriazen-3-ylmethyl)methylamines (1,9-diaryl-3,5,7-trimethyl-1,2,3,5,7,8,9-hepta-azanona-1,8-dienes): novel coupling products from the reaction of arenediazonium ions with methylamine and formaldehyde , 1983 .

[24]  K. Vaughan,et al.  13 C and 1H nuclear magnetic resonance study of solvent effects on tautomerism in 1-aryl-3-methyltriazenes , 1981 .

[25]  J. Hickman,et al.  α-hydroxylated derivatives of antitumour dimethyltriazenes , 1978 .

[26]  D. Hey,et al.  119. Union of aryl nuclei. Part VI. Reactions with 1-aryl-3 : 3-dimethyltriazens , 1943 .