BIOMAT Database Logo BIOMAT Database Logo

Efficient and beta-stereoselective synthesis of 4(5)-methyl-5(4)-(5-amino-5-deoxy-beta-D-ribofuranosyl)imidazole and related compounds exhibiting antiulcer activity. 1997

S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
Osaka University of Pharmaceutical Sciences, Japan.

The reaction of 2,3,5-tri-O-benzyl-D-ribose with the lithium salt of an imidazole derivative gave an adduct 17RS. Treatment of 17RS with 1.5N HCl in refluxing tetrahydrofuran gave the beta-4(5)-ribofuranosylimidazole 19 (35%) and the ribosylimidazole 18 (51%). The latter was converted into beta-19 in 86% yield by the Mitsunobu cyclization. This synthetic method produced only the desired beta-anomer. Protection of the imidazole nitrogen of 19 with an ethoxycarbonyl group followed by debenzylation gave 21, which was successively derived to the 5'-amino derivative 1 via the 5'-substituted phthalimide 23, followed by hydrazine degradation in excellent yield. Compound 1 was then converted into the 5'-cyanoguanidine 2 in 79% yield. The 5'-amino derivatives 3-9 lacking a methyl group were efficiently synthesized. Among them, the cyanoguanidine 5 and phenylthiourea 8 exhibited antiulcer activities with half the efficacy of cimetidine. The molecular conformation of 5 was determined by X-ray structure analysis.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D008297 Male Males
D002927 Cimetidine A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output. Altramet,Biomet,Biomet400,Cimetidine HCl,Cimetidine Hydrochloride,Eureceptor,Histodil,N-Cyano-N'-methyl-N''-(2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)guanidine,SK&F-92334,SKF-92334,Tagamet,HCl, Cimetidine,Hydrochloride, Cimetidine,SK&F 92334,SK&F92334,SKF 92334,SKF92334
D006146 Guanidines A family of iminourea derivatives. The parent compound has been isolated from mushrooms, corn germ, rice hulls, mussels, earthworms, and turnip juice. Derivatives may have antiviral and antifungal properties.
D006168 Guinea Pigs A common name used for the genus Cavia. The most common species is Cavia porcellus which is the domesticated guinea pig used for pets and biomedical research. Cavia,Cavia porcellus,Guinea Pig,Pig, Guinea,Pigs, Guinea
D006325 Heart Atria The chambers of the heart, to which the BLOOD returns from the circulation. Heart Atrium,Left Atrium,Right Atrium,Atria, Heart,Atrium, Heart,Atrium, Left,Atrium, Right
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000897 Anti-Ulcer Agents Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. Anti-Ulcer Drugs,Agents, Anti-Ulcer,Anti Ulcer Agents,Anti Ulcer Drugs,Drugs, Anti-Ulcer
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013276 Stomach Ulcer Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS). Gastric Ulcer,Gastric Ulcers,Stomach Ulcers,Ulcer, Gastric,Ulcer, Stomach,Ulcers, Gastric,Ulcers, Stomach

Related Publications

S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
Synthesis of 5-amino-1-(5-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide and related 5'-deoxyimidazole ribonucleosides.
December 1975, Journal of medicinal chemistry,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
Synthesis and enzymatic polymerisation of 5-amino-1-(2'-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide-5'- triphosphate.
December 1990, Nucleic acids research,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
[Synthesis and properties of 5-acetyl-4-methyl-1-(beta-d-ribofuranosyl)-imidazole-5' di-and-triphosphate].
January 1975, Zeitschrift fur Naturforschung. Section C, Biosciences,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
A new synthesis of inosine from 5-amino-1-beta-D-ribofuranosyl-4-imidazole-carboxamide.
January 1976, Nucleic acids research,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
Pyrrolopyrimidine nucleosides. 18. Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-beta-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine-5-carboxamide (2'-deoxysangivamycin).
January 1983, Journal of medicinal chemistry,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
An efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenine and related compounds from 2-amino-2-deoxy-D-glucose.
December 1989, Carbohydrate research,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
Design, synthesis and antiviral activity of novel 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d][1,2,3]triazines and the novel 3-amino-5-methyl-1-(beta-D-ribofuranosyl)- and 3-amino-5-methyl-1-(2-deoxy-beta-D-ribofuranosyl)-1,5-dihydro-1,4,5,6,7,8-hexaazaacenaphthylene as analogues of triciribine.
June 2005, Journal of medicinal chemistry,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
[Synthesis and photochemical properties of 1'-(2'-deoxy-beta-D-ribofuranosyl)-(4-3H)-5-ethyluracil].
July 1969, Zeitschrift fur Naturforschung. Teil B, Chemie, Biochemie, Biophysik, Biologie und verwandte Gebiete,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
Synthesis of 2-(3'-azido- and 3'-amino-3'-deoxy-beta-D-ribofuranosyl)thiazole-4-carboxamide.
November 2003, Nucleosides, nucleotides & nucleic acids,
S Harusawa, and H Moriyama, and Y Murai, and T Imazu, and H Ohishi, and R Yoneda, and T Kurihara, and H Hata, and Y Sakamoto
Stereoselective synthesis of [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives.
September 2001, Carbohydrate research,
Copied contents to your clipboard!