Interferons

Murthy, Y. K. S.; Anders, Hans-Peter

doi:10.1002/anie.197004801

Cited by 9 publications

References 84 publications

(4 reference statements)

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Synthesis of 3‐ and 4‐(β‐D‐ribofuranosyl)‐s‐triazolo[2,3‐a] pyrimid‐7‐one, isomers of inosine containing a bridgehead nitrogen atom

Winkley

Judd

Robins

1971

Journal of Heterocyclic Chem

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The first synthesis of a purine nucleoside analog containing a bridgehead nitrogen atom is here reported. The direct glycosylation of the trimethylsilyl derivative of s‐triazolo[2,3‐a] pyrimid‐7‐one has been shown to give 3‐(β‐D‐ribofuranosyl)‐s‐triazolo[2,3‐a]pyrimid‐7‐one (V) and 4‐(β‐D‐ribof'uranosyl)‐s‐lriazolo[2,3‐α]pyrimid‐7‐one (VII). The nueleoside V may he considered a close analog of inosine in which the nitrogen N1 and C5 of inosine have been interchanged. Bro‐minalion of the tri‐O‐acelyl derivative IV gave, after deblocking, 6‐bromo‐3‐(β‐D‐ribofurnaosyl)‐s‐triazolo[2,3‐a] pyrimid‐7‐one (IX). Structural assignments of the nucleosides were made on the basis of comparison of the ultraviolet absorption spectral characteristics with 3‐methyl‐s‐triazolo‐[2,3‐a]pyrimid‐7‐one (XI) and 4‐methyl‐s‐lriazolo[2,3‐a Jpyrimid‐7‐one (XII) prepared by a standard procedure from 7‐methoxy‐s‐triazolo(2,3‐a] pyrimidine (X).

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Synthesis of 3‐ and 4‐(β‐D‐ribofuranosyl)‐s‐triazolo[2,3‐a] pyrimid‐7‐one, isomers of inosine containing a bridgehead nitrogen atom

Winkley

Judd

Robins

1971

Journal of Heterocyclic Chem

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Synthesis and properties of alternating copolymers of potential antitumor activity containing 5‐fluorouracil

Umrigar

Ohashi

Butler

1979

J. Polym. Sci. Polym. Chem. Ed.

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Synopsis"Pyran" copolymer, the 2:1 regularly alternating cyclocopolymer (DVE-MA) of maleic anhydride (MA) and divinyl ether (DVE), first discovered in 1951, has been investigated extensively, both from the standpoint of its chemical structure and its biological activity. Although certain aspects of its structure remain to be determined, it has been shown to possess a wide spectrum of biological activity. It possesses antitumor activity and has been investigated clinically. During the clinical investigation, it was found to be an interferon inducer. Interferon is a protein which appears to be the body's first line of defense against viral infection. D V E M A also possesses antiviral, antibacterial, antifungal, antiarthritic, and anticoagulant properties, activates macrophages, inhibits reverse transcriptase, and is capable of elimination of Pu. During the course of investigations in these laboratories, many structural modifications of DVE-MA have been made. Many of these modifications also possess considerable antitumor activity and interferon-induction capability. Perhaps the most interesting structural modification has been the incorporation of 5-fluorouracil(5-FU) into the polymer (NSC 255083). This polymer has shown ( T / C ) I , [= ratio of test (7') to control (C) survival times] = 189 for dose by intraperitoneal injection of 200 mg/kg animal weight in CDBF, mice (6/6 survivors after fifth day) against P388 lymphocytic leukemia. This article describes the synthesis of both the monomer and copolymer, and a study of the hydrolytic rate of release of 5-FU from the polymer.

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Chemical transformations of cyclo and related polymers

Butler

1975

J. polym. sci., C Polym. symp.

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The 1:2 regularly alternating copolymer of divinyl ether and maleic anhydride produced via the cyclocopolymerization mechanism has been converted to a number of derivatives, and certain of these derivatives have been found useful as antitumor agents. Citraconic anhydride was substituted for maleic anhydride in the above cyclocopolymerization and its derivatives also exhibited antitumor properties, as did the derivatives of the copolymers of furan with maleic anhydride and with itaconic anhydride, respectively. The divinyl ether‐maleic anhydride copolymer reacts with dimethylformamide to yield a copolymer possessing polyelectrolyte character. The completely methylated copolymer was found to be useful in determining the molecular weight distribution of the original copolymer by gel permeation chromatography. A second series of reactive polymers were prepared by cationic initiation of o‐, m‐, and p‐(2‐vinyloxy)ethoxy‐β‐nitrostyrenes, propagation occurring only through the vinyloxy group. The polymer of the p‐isomer was crosslinked through anionic initiation on the nitrovinyl group. The m‐ and p‐isomers were converted to linear polymers through the nitrovinyl group via anionic initiation which underwent crosslinking through the vinyloxy group upon standing in air. The o‐isomer was not converted to polymer via anionic initiation. This unusual “ortho effect” appears to be a steric effect, as the only ortho derivative of β‐nitrostyrene which has been polymerized by anionic initiation is o‐fluoro‐β‐nitrostyrene. Poly‐m‐β‐dinitrostyrene was converted to the polyanion by sodium methoxide. A third series of reactive polymers were synthesized via anionic initiation on the o‐, m‐, and p‐(2‐vinyloxy)ethoxystyrenes. Propagation occurred through the styrene double bond leaving the vinyloxy group pendant. Hydrolysis of this vinyl ether was accomplished in all cases to yield the poly‐2‐hydroxyethylstyrenes. Further reactions of these polymers with acrylonitrile, phenyl isocyanate, and diisocyanates led to new polymeric systems. Hydrolysis of the vinyloxy group of the original styrenes followed by esterification with acrylyl chlorides led to monomers that were cyclopolymerized by a radical mechanism to polymers containing ten‐membered rings.

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Interferons

Cited by 9 publications

References 84 publications

Synthesis of 3‐ and 4‐(β‐D‐ribofuranosyl)‐s‐triazolo[2,3‐a] pyrimid‐7‐one, isomers of inosine containing a bridgehead nitrogen atom

Synthesis of 3‐ and 4‐(β‐D‐ribofuranosyl)‐s‐triazolo[2,3‐a] pyrimid‐7‐one, isomers of inosine containing a bridgehead nitrogen atom

Synthesis and properties of alternating copolymers of potential antitumor activity containing 5‐fluorouracil

Chemical transformations of cyclo and related polymers

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