CA2616028A1 - Synthese de scabronines et analogues de ceux-ci - Google Patents

Info

Publication number

CA2616028A1

CA2616028A1 CA002616028A CA2616028A CA2616028A1 CA 2616028 A1 CA2616028 A1 CA 2616028A1 CA 002616028 A CA002616028 A CA 002616028A CA 2616028 A CA2616028 A CA 2616028A CA 2616028 A1 CA2616028 A1 CA 2616028A1

Authority

CA

Canada

Prior art keywords

moiety

substituted

unsubstituted

branched

compound

Prior art date

2005-07-22

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 238000003786 synthesis reaction Methods 0.000 title abstract description 29
• 230000015572 biosynthetic process Effects 0.000 title abstract description 28
• 229930188740 scabronine Natural products 0.000 title abstract description 12
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• 238000000034 method Methods 0.000 claims abstract description 31
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• 125000001931 aliphatic group Chemical group 0.000 claims description 88
• 125000003118 aryl group Chemical group 0.000 claims description 74
• 229910052739 hydrogen Inorganic materials 0.000 claims description 69
• 239000001257 hydrogen Substances 0.000 claims description 69
• 125000001072 heteroaryl group Chemical group 0.000 claims description 62
• 125000004122 cyclic group Chemical group 0.000 claims description 60
• 125000002015 acyclic group Chemical group 0.000 claims description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
• 125000002252 acyl group Chemical group 0.000 claims description 46
• 125000006239 protecting group Chemical group 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 125000004414 alkyl thio group Chemical group 0.000 claims description 28
• 125000005110 aryl thio group Chemical group 0.000 claims description 28
• 125000004104 aryloxy group Chemical group 0.000 claims description 28
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 28
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• 150000002367 halogens Chemical group 0.000 claims description 26
• 125000003282 alkyl amino group Chemical group 0.000 claims description 25
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
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• 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
• 230000003301 hydrolyzing effect Effects 0.000 claims description 2
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• 150000002431 hydrogen Chemical class 0.000 claims 15
• PDFVQJPCHCWDIY-YSGRDPCXSA-N (3as,5ar,10ar)-8-formyl-5a-methyl-6-oxo-1-propan-2-yl-3,4,5,7,10,10a-hexahydro-2h-cyclohepta[g]indene-3a-carboxylic acid Chemical compound C([C@@H]12)C=C(C=O)CC(=O)[C@]1(C)CC[C@]1(C(O)=O)C2=C(C(C)C)CC1 PDFVQJPCHCWDIY-YSGRDPCXSA-N 0.000 abstract description 36
• QZEMMWXYJUKIBS-UHFFFAOYSA-N scabronine G Natural products C=1C(O)C2(C)CCC3(C)CCC(C(CO)C)=C3C2CC(O)C=1COC(=O)C1=CC=CC=C1 QZEMMWXYJUKIBS-UHFFFAOYSA-N 0.000 abstract description 30
• 230000000508 neurotrophic effect Effects 0.000 abstract description 13
• 230000004770 neurodegeneration Effects 0.000 abstract description 11
• 150000004141 diterpene derivatives Chemical class 0.000 abstract description 3
• -1 methyl ester derivative of scabronine G Chemical class 0.000 description 140
• 239000000203 mixture Substances 0.000 description 64
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 101150041968 CDC13 gene Proteins 0.000 description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
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• 239000000243 solution Substances 0.000 description 29
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