Ciba Foundation Symposium - Chemistry and Biology of Purines by G. E. W. and O'Connor, Cecilia M. Wolstenholme

By G. E. W. and O'Connor, Cecilia M. Wolstenholme

Chapter 1 establishing feedback (pages 1–2):
Chapter 2 Synthesis and homes of Purines of power organic curiosity (pages 3–19): Aaron Bendich, Alfredo Giner?Sorolla and Jack J. Fox
Chapter three a few artificial stories on Purines and similar Heterocycles (pages 20–38): E. C. Taylor, T. S. Osdene, E. Richter and O. Vogl
Chapter four a few New N?Methylpurines (pages 39–49): Gertrude B. Elion
Chapter five The constitution of the Hydroxypurines Investigated through O? and N?Methylation (pages 50–59): D. J. Brown
Chapter 6 The Spectra and constitution of the Monohydroxypurines and different very likely Tautomeric Purines (pages 60–71): S. F. Mason
Chapter 7 The ??Electron houses of Purine Calculated through the L.C.A.O. procedure (pages 72–76): S. F. Mason
Chapter eight The Degradation of Uric Acid via Water stressed (pages 77–96): Wolfgang Pfleiderer
Chapter nine The 8?Position in Purines. The Chemical and organic Transformation of Purines Into Pteridines (pages 97–107): Adrien Albert
Chapter 10 Cyclonucleosides (pages 108–119): D. M. Brown, Sir Alexander Todd and S. Varadarajan
Chapter eleven Stereochemistry of Nucleoside Synthesis (pages 120–133): B. R. Baker
Chapter 12 artificial Chemical Investigations regarding the Metabolism of Purines (pages 134–145): G. M. Timmis, I. Cooke and R. G. W. Spickett
Chapter thirteen the results of strength Antipurines on a Purine?Requiring pressure of Escherichia coli (pages 146–159): H. O. J. Collier and Patricia L. Huskinson
Chapter 14 The Chemistry of latest Purines within the B (pages 160–168): E. Lester Smith
Chapter 15 organic and Microbiological task of Purine Analogues of nutrition B (pages 169–176): S. okay. Kon
Chapter sixteen Puromycin (pages 177–191): Brian L. Hutchings
Chapter 17 Chemical and organic Behaviours of 9???d?Ribofuranosylpurine (pages 192–203): G. B. Brown, M. P. Gordon, D. I. Magrath and A. Hampton
Chapter 18 at the Activation of the One?Carbon Unit for the Biosynthesis of Purine Nucleotides (pages 204–232): G. Robert Geeenberg and Lothar Jaenicke
Chapter 19 The Enzymatic Synthesis of Inosinic Acid De Novo (pages 233–255): J. M. Buchanan, J. G. Flaks, S. C. Hartman, B. Levenberg, L. N. Lukens and L. Warren
Chapter 20 Enzymic keep watch over of Purines through Xanthine Oxidase (pages 256–269): F. Bergel, R. C. Bray, A. Haddow and that i. Lewin
Chapter 21 The organic results of 8?Azapurines (pages 270–285): R. E. F. Matthews
Chapter 22 Biochemical results of 6?Mercaptopurine (pages 286–308): Gertrude B. Elion and George H. Hitchings
Chapter 23 using 6?Mercaptopurine within the remedy of Leukaemia (pages 299–307): D. A. G. Galton
Chapter 23 common dialogue (pages 308–317):

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81, ed. Chargaff and J. N. Devidson. New York: Academic Press. BENDICH, A,, RUSSELL, P. , and Fox, J. J. (1954). J . Amer. chem. ,76, 6073. PURINES AND RELATED HETEROCYCLES 33 BENSON, F. , HARTZEL, L. , and SAVELL,W. L. (1950). J. Amm. chem. ,72, 1816. BURCHENAL, J. H. (1954). Fed. , 13, 760. COOE, A. , and THOMAS, G. H. (1950). J. chem. ,1888, and preceding papers in this series. CRIPPA, G. , and PERRONCITO, G. (1936). Gazz. chim. , 66, 649. DARAPSKY, A,, and HILLERS, D. (1915). J. prakt. , (2), 92, 297.

TAYLOR, T. S. OSDENE,E. RICHTER, 0. VOGL hydrolysis. Condensation of XIX with a : p-dicarbonyl compounds produced the purine analogues (XX). The product formed with glyoxal, 3-hydroxypyrazolo(3 : 4-b)pyrazine, is a structural isomer of hypoxanthine. The required pyrazole intermediate XIX was alternatively prepared from ethyl isonitrosocyanoacetate (XXI). Treatment of XXI with two molar equivalents of hydrazine in ethanol solution yielded XXII (Darapsky and Hillers, 1915), which upon base-catalysed intramolecular cyclization to 3hydroxy-4-nitroso-5-aminopyrazole (XXIII) (Hepner and Fajersztejn, 1937) followed by reduction yielded XIX.

Here, it is true, we had to reckon with the presence of EtOOC-C=CHOEt I CN three different reactive groups : cyano, carbethoxy and aldehyde, a fact which could complicate the reaction with hydrazine. Surprisingly enough, the carbethoxy group takes no part in the reaction so that the carbethoxyaminopyrazole was obtained in excellent yield. This reacts with formamide to give a compound isomeric with hypoxanthine, and with urea to give a xanthine isomer (Fig. 3). 3. g. the caffeine isomer (Fig. 4) shows properties very similar to those of caffeine.

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