Synthesis of Triazole and Coumarin Compounds and Their Physiological Activity

Seventy three coumarinc derivatives were synthesized. The structures of these obtained products wereproved on the basis of spectral and analytical data. A comparative pharmacological study showed thatthese compounds have different anticoagulant and antiinflammatory activities. The most prospective compoundsare with enhance activity.

[1]  H. Zou,et al.  A novel one-pot reformatsky type reaction via bismuth salt in aqueous media , 1997 .

[2]  E. F. Van Maanen,et al.  Central nervous system effects of thalidomide. , 1961, The Journal of pharmacology and experimental therapeutics.

[3]  T. Hoye,et al.  Double (internal/external) alkyne insertion reactions of α-diazoketones , 1991 .

[4]  M. Franck-Neumann.  Synthesis of gem‐Dimethylcyclopropanes by means of 2‐Diazopropane , 1968 .

[5]  N. Al-Masoudi,et al.  Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives. , 2004, Farmaco.

[6]  J. Fox,et al.  A copper-catalyzed method for the facially selective addition of grignard reagents to cyclopropenes. , 2002, Journal of the American Chemical Society.

[7]  N. Heindel,et al.  Improved syntheses of 5‐substituted‐4‐amino‐3‐mercapto‐(4H)‐1,2,4‐triazoles , 1976 .

[8]  Anthony B. Pinkerton,et al.  Bull. Soc. Chim. Fr. , 1957 .

[9]  A. Mustafa,et al.  Reaktionen substituierter Cumarine, Furocumarine und Khellinon‐styryl‐Derivate mit Hydrazin und Phenylhydrazin , 1966 .

[10]  R. Moffett.  CENTRAL NERVOUS SYSTEM DEPRESSANTS. VII. PYRIDYL COUMARINS. , 1964, Journal of medicinal chemistry.

[11]  M. Ghate,et al.  Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents. , 2003, European journal of medicinal chemistry.

[12]  E. Nakamura,et al.  Iron-Catalyzed Olefin Carbometalation , 2000 .

[13]  O. Wolfbeis,et al.  Zur Reaktivität von C=N-Doppelbindungssystemen, X Synthesen von kondensierten Heterocyclen. / The Reactivity of C=N-Double Bond Systems, Χ Synthesis of Condensed Heterocycles , 1976 .

[14]  R. K. Robins,et al.  Design, synthesis, and broad spectrum antiviral activity of 1-.beta.-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides , 1972 .

[15]  H. Lehmkuhl,et al.  Addition von Organomagnesiumhalogeniden an C C-Bindungen, XIII. Anlagerungen von Alkylmagnesiumhalogeniden an 3,3-Dimethylcyclopropen; ein neuer Weg zu cis- oder trans-Chrysanthemsäure , 1978 .

[16]  T. Ye,et al.  Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides , 1998 .

[17]  M. Aburada,et al.  The choleretic mechanism of coumarin compounds and phenolic compounds. , 1981, Journal of pharmacobio-dynamics.

[18]  T. Katsuki.  Chiral Metallosalen Complexes: Structures and Catalyst Tuning for Asymmetric Epoxidation and Cyclopropanation , 2002 .

[19]  R. Zimmer,et al.  Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis. , 2003, Chemical reviews.

[20]  T. Yamazaki,et al.  Synthesis and taste properties of L-aspartyl-methylated 1-aminocyclopropanecarboxylic acid methyl esters , 1992 .

[21]  D. Egan,et al.  The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds. , 1990, Drug metabolism reviews.

[22]  A. Deana,et al.  2-(Aminomethyl)phenols, a new class of saluretic agents. 5. Fused-ring analogues. , 1983, Journal of medicinal chemistry.

[23]  N. Shimma,et al.  Modeling, synthesis and biological activity of novel antifungal agents (1). , 1998, Bioorganic & medicinal chemistry letters.

[24]  A. Charette,et al.  Stereoselective cyclopropanation reactions. , 2003, Chemical reviews.

[25]  V. Dixit,et al.  New novel non-steroidal antifertility agents , 1980, Naturwissenschaften.

[26]  Gene-Hsiang Lee,et al.  Dirhodium(II) tetra(N-(dodecylbenzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes. , 2004, Organic letters.

[27]  N. Al-Masoudi,et al.  Synthesis of 3′-1,2,4-triazolo- and 3′-1,3,4-thiadiazoliminothymidines , 2003 .

[28]  E. Nakamura,et al.  Homogeneous sonochemistry in radical chain reactions: sonochemical hydrostannation and tin hydride reduction , 1989 .

[29]  M. Weissenfels,et al.  Heterocyclisch [c]‐anellierte Cumarine aus 4‐Azido‐3‐cumarincarbaldehyden , 1992 .

[30]  K. W. Merz,et al.  Über kondensationen von nicotinoylessigester mit aromatischen diaminen , 1964 .

[31]  K. Takagi,et al.  Synthesis and analgesic activity of 4-amino-1,2-dihydro-5-(2-hydroxyphenyl)-3H-pyrazol-3-ones and 5-amino-6-(2-hydroxyphenyl)pyrimidin-4(3H)-ones , 1987 .

[32]  R. Giridhar,et al.  Synthesis and pharmacological investigation of novel 1-substituted-4-phenyl-1,2,4-triazolo[4,3-a]quinazolin-5(4H)-ones as a new class of H1-antihistaminic agents. , 2005, Bioorganic & Medicinal Chemistry Letters.

[33]  G. RicheyJrH,et al.  アリルGrignard試薬の3-(ヒドロキシメチル)シクロプロペン類への付加の立体化学 , 1980 .

[34]  K. P. Link,et al.  Studies on 4-Hydroxycoumarin. VII. Reactions of 4-Hydroxycoumarin with Cationoid Reagents1 , 1945 .

[35]  Rouvain M. Bension,et al.  Stereochemistry of addition of allylic Grignard reagents to 3-(hydroxymethyl)cyclopropenes , 1980 .

[36]  E. Essassi,et al.  Nouvelle synthèse des benzodiazépines-1,5 à partir de la γ-pyrone , 1987 .

[37]  M. M. Díaz‐Requejo,et al.  A family of highly active copper(I)-homoscorpionate catalysts for the alkyne cyclopropenation reaction. , 2001, Chemical communications.

[38]  N. Trinajstic,et al.  Chemistry of Coumarins. ‐ Nucleophilic Substitutions of 4‐Chloro‐3‐nitrocoumarin with Hard and Soft Nucleophiles , 1983 .

[39]  A. Demonceau,et al.  Transition-metal-catalyzed reaction of diazocompounds, efficient synthesis of functionalized ethers by carbene insertion into the hydroxylic bond of alcohols , 1982 .

[40]  M. V. Paradkar,et al.  A novel synthesis of 4-aminomethylcoumarins , 1986 .

[41]  E. Nakamura,et al.  Hydrostannation of Cyclopropene. Strain-Driven Radical Addition Reaction , 1994 .