Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity
The total syntheses of (-)-cylindrocyclophane A (1), a naturally occurring, cytotoxic [7.7]paracyclophane, and its enantiomer have been achieved in an enantiodivergent manner starting from a chiral propargyl alcohol building block using Smith's cross metathesis/ring-closing metathesis protocol...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2009-01, Vol.7 (18), p.3772-3781 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Yamakoshi, Hiroyuki Ikarashi, Fumiya Minami, Masataka Shibuya, Masatoshi Sugahara, Tsutomu Kanoh, Naoki Ohori, Hisatsugu Shibata, Hiroyuki Iwabuchi, Yoshiharu |
| description | The total syntheses of (-)-cylindrocyclophane A (1), a naturally occurring, cytotoxic [7.7]paracyclophane, and its enantiomer have been achieved in an enantiodivergent manner starting from a chiral propargyl alcohol building block using Smith's cross metathesis/ring-closing metathesis protocol as the key step. The biological evaluation of both enantiomers of cylindrocyclophane A (1 and ent-1) and its analogues indicated that the chirality of 1 is irrelevant to its cytotoxicity, which is attributed to the resorcinol motifs embedded in the robust [7.7]paracyclophane framework. |
| doi_str_mv | 10.1039/b909646a |
| format | Article |
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| ispartof | Organic & biomolecular chemistry, 2009-01, Vol.7 (18), p.3772-3781 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alcohols - chemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological Products - chemical synthesis Biological Products - chemistry Biological Products - pharmacology Cell Proliferation HCT116 Cells Humans Polycyclic Aromatic Hydrocarbons - chemical synthesis Polycyclic Aromatic Hydrocarbons - chemistry Polycyclic Aromatic Hydrocarbons - pharmacology Polycyclic Compounds - chemical synthesis Polycyclic Compounds - chemistry Polycyclic Compounds - pharmacology Stereoisomerism Structure-Activity Relationship |
| title | Syntheses of naturally occurring cytotoxic [7.7]paracyclophanes, (-)-cylindrocyclophane A and its enantiomer, and implications for biological activity |
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