Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic
Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influ...
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| Published in: | Bioorganic & medicinal chemistry Vol. 15; no. 1; pp. 424 - 432 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
2007
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| Abstract | Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of
o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. |
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| AbstractList | Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. |
| Author | Sasaki, Kazushige Nemoto, Hideo Matsuya, Yuji Ochiai, Hiroshi |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/17035034$$D View this record in MEDLINE/PubMed |
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| Keywords | Perhydrophenanthrenes mRNA Anti-influenza agents Cage structure |
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| References | Pinto, Holsinger, Lamb, Hayden, Hay (bib2) 1992; 69 Kametani, Kajiwara, Fukumoto (bib11) 1974; 30 Parkes, Ermert, Fässler, Ives, Martin, Merrett, Obrecht, Williams, Klumpp, Singh, Tomassini (bib4) 2003; 46 Matsuya, Sasaki, Nagaoka, Kakuda, Toyooka, Imanishi, Ochiai, Nemoto (bib8) 2004; 69 Service (bib1) 1997; 275 White, Kielian, Helenius (bib14) 1983; 16 . Mosmann (bib13) 1983; 65 Tobita, Mantani, Imanishi, Kawamata, Terasawa, Ochiai (bib12) 1975; 62 Ochiai, Sakai, Hirabayashi, Shimizu, Terasawa (bib15) 1995; 27 Toyooka, Nagaoka, Nemoto, Toyooka, Nagaoka, Sasaki, Qin, Kakuda, Nemoto, Matsuya, Qin, Nagaoka, Nemoto (bib10) 2001; 58 See, Ref. Nemoto, Fukumoto (bib9) 1998; 54 Roberts, Abdel-Magid, Maryanoff, Mehrman, McKimm-Breschkin (bib5) 2001; 56 Hay, Wolstenholme, Skehel, Smith (bib3) 1985; 4 Hayden, Osterhaus, Treanor, Fleming, Aoki, Nicholson, Bohnen, Hirst, Keene, Wightman, McKimm-Breschkin (bib6) 1997; 337 |
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o-quinodimethane chemistry with high generality and stereoselectivity, and found to... Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to... Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o- quinodimethane chemistry with high generality and stereoselectivity, and found to... |
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| SubjectTerms | Animals Anti-influenza agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Cage structure Cell Line Cell Proliferation - drug effects Dogs Dose-Response Relationship, Drug Drug Design Furans - chemistry Influenza A virus - drug effects Influenza A virus - growth & development Influenza B virus - drug effects Influenza B virus - growth & development Influenza virus Microbial Sensitivity Tests Molecular Structure mRNA Perhydrophenanthrenes Phenanthrenes - chemistry Stereoisomerism Structure-Activity Relationship Virus Replication - drug effects |
| Title | Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic |
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