- Gram-level total synthesis method of sulfur onium salt type natural product neoponkoranol extracted from salacia plants
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The invention belongs to the field of chemical synthesis and particularly relates to a gram-level total synthesis method of a sulfur onium salt type natural product neoponkoranol with hypoglycemic activity extracted from salacia plants. According to the m
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Paragraph 0057; 0058; 0059; 0060
(2019/02/19)
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- Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity
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Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring α-glucosidase inhibitor, salacinol (1a), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-d- arabinitol (3), with cyclic sulfates (8, 9, and 10), and their α-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents for the α-glucosidase inhibitory activity. A practical synthetic route to 3 starting from d-xylose is also described.
- Muraoka, Osamu,Yoshikai, Kazuya,Takahashi, Hideo,Minematsu, Toshie,Lu, Guangxin,Tanabe, Genzoh,Wang, Tao,Matsuda, Hisashi,Yoshikawa, Masayuki
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p. 500 - 509
(2007/10/03)
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- 2'-deoxy-2'-(substituted or unsubstituted)methylidene-4'-thionucleosides
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The present invention relates to 2'-deoxy-2'-(substituted or unsubstituted)methylidene-4'-thionucleosides having excellent antitumor activity, represented by formula ?I!: STR1 wherein B represents a pyrimidine or purine base, R1 and R2, which may be the same or different, represent hydrogen, a cyano group or alkyl group, and R3 represents hydrogen or a phosphoric acid residue, and a method for producing the same, and a use of the same.
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- Purine 4'-thioarabinonucleosides
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The present invention provides a novel purine 4'-thioarabinonucleoside represented by the following formula ?1!: STR1 wherein B represents a purine base other than adenine. Also disclosed are a method for preparing the purine 4'-thioarabinonucleoside and pharmaceutical compositions containing the purine 4'-thioarabinonucleoside.
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- A Novel Synthesis of 2′-Modified 2′-Deoxy-4′-thiocytidines from D-Glucose
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Novel 2′-deoxycytidine antimetabolites, specifically several 2′-modified 2′-deoxy-4′-thiocytidines, were synthesized as potential new antineoplastic agents. Methyl 3-O-benzylxylofuranoside was converted to a 1,4-anhydro-4-thioarabitol 24. Protection of the primary alcohol of 24 gave a common intermediate (15) which was useful for the synthesis of various 2′-modified 2′-deoxy-4′-thionucleosides. Oxidation of the secondary hydroxyi group of 15, followed by the Wittig reaction or treatment with (diethylamido)sulfur trifluoride (DAST) produced 2-deoxy-2-methylene (26) and 2-deoxy-2,2-difluoro (34) derivatives, respectively. Unique Pummerer-type glycosylation between the corresponding sulfoxides and trimethylsilylated N4-acetylcytosine produced 2′-deoxy-2′-methylene- (10) and 2′-deoxy-2′,2′-difluoro-4′-thiocytidines (11). On the other hand, treatment of 15 with DAST introduced a fluorine atom with retention of the 2′-stereochemistry, yielding 40. In contrast, the Mitsunobu reaction of 3-O-benzoyl derivative 53 which was obtained from 15 in five steps, using diphenylphosphoryl azide gave azide derivative 54 with inverted stereochemistry. These derivatives were converted to the corresponding 1-O-acetyl derivatives via the usual Pummerer rearrangement, which were in turn used to synthesize 4′-thiocytidines 12 and 58. Among the 2′-modified 4′-thiocytidines obtained, 2′-methylene (10) and 2′-fluoro (12) derivatives were found to have potent antineoplastic properties in vitro.
- Yoshimura, Yuichi,Kitano, Kenji,Yamada, Kohei,Satoh, Hiroshi,Watanabe, Mikari,Miura, Shinji,Sakata, Shinji,Sasaki, Takuma,Matsuda, Akira
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p. 3140 - 3152
(2007/10/03)
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- Synthesis and biological activities of 2'-modified 4'-thionucleosides
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We have synthesized 4'-thioDMDC, 4'-thiogemcitabine, and 4'- thioarabinonucleosides, as potential antitumor and antiviral agents, originated from D-glucose. Biological activities of these compounds are also described.
- Yoshimura, Yuichi,Kitano, Kenji,Watanabe, Mikari,Satoh, Hiroshi,Sakata, Shinji,Miura, Shinji,Ashida, Noriyuki,Machida, Haruhiko,Matsuda, Akira
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p. 1103 - 1106
(2007/10/03)
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- Synthesis of iminothiasugar as a potential transition-state analog inhibitor of glycosyltransfer reactions
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Iminothiasugar 1, a potential transition-state analog inhibitor of glycosidases, was synthesized in 10 steps from D-xylose.
- Yuasa, Hideya,Kajimoto, Tetsuya,Wong, Chi-Huey
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p. 8243 - 8246
(2007/10/02)
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