PT78819B - Rooperol and its derivatives - Google Patents
Rooperol and its derivatives Download PDFInfo
- Publication number
- PT78819B PT78819B PT78819A PT7881984A PT78819B PT 78819 B PT78819 B PT 78819B PT 78819 A PT78819 A PT 78819A PT 7881984 A PT7881984 A PT 7881984A PT 78819 B PT78819 B PT 78819B
- Authority
- PT
- Portugal
- Prior art keywords
- alkyl
- substituents
- product
- group
- compound
- Prior art date
Links
- JQPOMMNEABQHEU-DUXPYHPUSA-N 4-[(e)-5-(3,4-dihydroxyphenyl)pent-1-en-4-ynyl]benzene-1,2-diol Chemical compound C1=C(O)C(O)=CC=C1\C=C\CC#CC1=CC=C(O)C(O)=C1 JQPOMMNEABQHEU-DUXPYHPUSA-N 0.000 title abstract description 5
- JQPOMMNEABQHEU-UHFFFAOYSA-N rooperol Natural products C1=C(O)C(O)=CC=C1C=CCC#CC1=CC=C(O)C(O)=C1 JQPOMMNEABQHEU-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 150000004820 halides Chemical class 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001408 amides Chemical class 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims 1
- XAJOPMVSQIBJCW-UHFFFAOYSA-N 3-penten-1-yne Chemical group CC=CC#C XAJOPMVSQIBJCW-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 11
- 230000010261 cell growth Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004113 cell culture Methods 0.000 description 4
- NKCXUXCXXINIMN-LITNSJRUSA-N (2S,3R,4S,5S,6R)-2-[2-hydroxy-4-[(E)-5-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]pent-1-en-4-ynyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC=C1\C=C\CC#CC(C=C1O)=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 NKCXUXCXXINIMN-LITNSJRUSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- NKCXUXCXXINIMN-UHFFFAOYSA-N hypoxoside Natural products OC1C(O)C(O)C(CO)OC1OC(C(=C1)O)=CC=C1C=CCC#CC(C=C1O)=CC=C1OC1C(O)C(O)C(O)C(CO)O1 NKCXUXCXXINIMN-UHFFFAOYSA-N 0.000 description 3
- 230000017095 negative regulation of cell growth Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 208000009956 adenocarcinoma Diseases 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 201000001441 melanoma Diseases 0.000 description 2
- 239000007758 minimum essential medium Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QUMSUJWRUHPEEJ-UHFFFAOYSA-N 4-Pentenal Chemical class C=CCCC=O QUMSUJWRUHPEEJ-UHFFFAOYSA-N 0.000 description 1
- 241000345998 Calamus manan Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000006145 Eagle's minimal essential medium Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000684187 Hakea nitida Species 0.000 description 1
- 241001495895 Hakea obtusa Species 0.000 description 1
- 240000006760 Holboellia latifolia Species 0.000 description 1
- 241001031163 Hymenochaetopsis rigidula Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 102000006995 beta-Glucosidase Human genes 0.000 description 1
- 108010047754 beta-Glucosidase Proteins 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/48—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon triple bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
- C07C33/042—Acyclic alcohols with carbon-to-carbon triple bonds with only one triple bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
- C07C33/048—Acyclic alcohols with carbon-to-carbon triple bonds with double and triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/28—Alcohols containing only six-membered aromatic rings as cyclic part with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
- C07C33/486—Polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838317850A GB8317850D0 (en) | 1983-06-30 | 1983-06-30 | Rooperol and its derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT78819A PT78819A (en) | 1984-07-01 |
| PT78819B true PT78819B (en) | 1986-06-18 |
Family
ID=10545081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT78819A PT78819B (en) | 1983-06-30 | 1984-06-29 | Rooperol and its derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4644085A (OSRAM) |
| EP (1) | EP0130829B1 (OSRAM) |
| JP (1) | JPS60105637A (OSRAM) |
| AR (1) | AR242017A1 (OSRAM) |
| AT (1) | ATE27599T1 (OSRAM) |
| AU (1) | AU569529B2 (OSRAM) |
| CA (1) | CA1293735C (OSRAM) |
| DE (1) | DE3464050D1 (OSRAM) |
| DK (1) | DK322984A (OSRAM) |
| ES (1) | ES8608462A1 (OSRAM) |
| GB (1) | GB8317850D0 (OSRAM) |
| GR (1) | GR79540B (OSRAM) |
| IE (1) | IE57563B1 (OSRAM) |
| IL (1) | IL72239A (OSRAM) |
| NO (1) | NO158376C (OSRAM) |
| NZ (1) | NZ208694A (OSRAM) |
| PT (1) | PT78819B (OSRAM) |
| ZA (1) | ZA844983B (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8317850D0 (en) * | 1983-06-30 | 1983-08-03 | Roecar Holdings Nv | Rooperol and its derivatives |
| FR2576897B1 (fr) * | 1985-02-01 | 1987-02-27 | Centre Nat Rech Scient | Nouveaux derives epoxydiques, leur preparation et leur application, notamment comme medicaments antitumoraux |
| ATE61329T1 (de) * | 1985-06-19 | 1991-03-15 | Rooperol Na Nv | Verfahren zur herstellung von rooperol, hypoxosid und deren derivaten. |
| US4956502A (en) * | 1985-06-19 | 1990-09-11 | Rooperol (N.A.) Nv | Process for the preparation of rooperol derivative |
| MX9305453A (es) * | 1992-09-07 | 1994-05-31 | Virostat Na Nv | Metodo para tratar infecciones virales. |
| US5569649A (en) * | 1994-06-14 | 1996-10-29 | Phytopharm (Na) N.V. | Anti-inflammatory treatment method |
| CN104513137B (zh) * | 2014-12-22 | 2016-05-04 | 陕西师范大学 | 一种1,5-烯炔醇类化合物及其合成方法和应用 |
| CN109704926B (zh) * | 2019-01-29 | 2022-02-08 | 南京工业大学 | 抗癌活性分子骨架1,4-烯炔类化合物及其制备方法与应用 |
| WO2023036995A1 (en) * | 2021-09-13 | 2023-03-16 | Centre National De La Recherche Scientifique | Alkynylcarbinols with high cytotoxicity |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE750532A (fr) * | 1969-05-26 | 1970-10-16 | Lilly Co Eli | Nouveaux diethynylcarbinols substitues |
| US3922266A (en) * | 1972-06-28 | 1975-11-25 | Sumitomo Chemical Co | Aryl ketones and production thereof |
| US4224244A (en) * | 1973-03-30 | 1980-09-23 | Hoffmann-La Roche Inc. | 9-Phenyl 5,6-dimethyl-nona-2,4,6,8 tetraenal or tetraenol derivatives |
| IT1022545B (it) * | 1973-10-01 | 1978-04-20 | Hoffmann La Roche | Procedimento per fabricare etinilcarbinoli |
| US4055575A (en) * | 1975-03-20 | 1977-10-25 | Scm Corporation | Synthesis of dehydrophytol and vitamin E |
| US4162265A (en) * | 1978-09-27 | 1979-07-24 | The United States Of America As Represented By The Secretary Of The Air Force | Aromatic enyne compounds and their synthesis |
| US4223172A (en) * | 1978-12-07 | 1980-09-16 | Gulf Research & Development Company | Process for the preparation of bromoarylacetylene and aryldiacetylene precursors |
| CH642936A5 (de) * | 1979-10-19 | 1984-05-15 | Hoffmann La Roche | Aethinylierung alpha,beta-ungesaettigter ketone. |
| US4345084A (en) * | 1981-06-29 | 1982-08-17 | Hoffmann-La Roche Inc. | Unsaturated eicosanoic acids |
| GB2120650A (en) * | 1982-04-19 | 1983-12-07 | Roecar Holdings Nv | Rooperol derivatives |
| CA1209912A (en) * | 1982-04-19 | 1986-08-19 | Siegfrid Drewes | Extract of plants of the family of hypoxidaceae for treatment of cancer |
| GB8317850D0 (en) * | 1983-06-30 | 1983-08-03 | Roecar Holdings Nv | Rooperol and its derivatives |
-
1983
- 1983-06-30 GB GB838317850A patent/GB8317850D0/en active Pending
-
1984
- 1984-06-26 CA CA000457433A patent/CA1293735C/en not_active Expired - Fee Related
- 1984-06-27 IL IL72239A patent/IL72239A/xx unknown
- 1984-06-27 NO NO842604A patent/NO158376C/no unknown
- 1984-06-27 AU AU29921/84A patent/AU569529B2/en not_active Ceased
- 1984-06-28 NZ NZ208694A patent/NZ208694A/xx unknown
- 1984-06-29 ZA ZA844983A patent/ZA844983B/xx unknown
- 1984-06-29 PT PT78819A patent/PT78819B/pt not_active IP Right Cessation
- 1984-06-29 DK DK322984A patent/DK322984A/da not_active Application Discontinuation
- 1984-06-29 IE IE1653/84A patent/IE57563B1/en not_active IP Right Cessation
- 1984-06-29 ES ES533884A patent/ES8608462A1/es not_active Expired
- 1984-06-29 GR GR75155A patent/GR79540B/el unknown
- 1984-06-29 AT AT84304498T patent/ATE27599T1/de not_active IP Right Cessation
- 1984-06-29 EP EP84304498A patent/EP0130829B1/en not_active Expired
- 1984-06-29 DE DE8484304498T patent/DE3464050D1/de not_active Expired
- 1984-06-29 AR AR84297018A patent/AR242017A1/es active
- 1984-06-30 JP JP59136404A patent/JPS60105637A/ja active Pending
-
1985
- 1985-06-04 US US06/740,969 patent/US4644085A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE27599T1 (de) | 1987-06-15 |
| GB8317850D0 (en) | 1983-08-03 |
| ES533884A0 (es) | 1986-04-01 |
| ES8608462A1 (es) | 1986-04-01 |
| IE841653L (en) | 1984-12-30 |
| AR242017A1 (es) | 1993-02-26 |
| CA1293735C (en) | 1991-12-31 |
| IL72239A0 (en) | 1984-10-31 |
| PT78819A (en) | 1984-07-01 |
| EP0130829A3 (en) | 1985-03-06 |
| NO842604L (no) | 1985-01-02 |
| NO158376C (no) | 1988-08-31 |
| DK322984D0 (da) | 1984-06-29 |
| IL72239A (en) | 1989-07-31 |
| IE57563B1 (en) | 1992-12-16 |
| AU2992184A (en) | 1985-01-03 |
| AU569529B2 (en) | 1988-02-04 |
| NZ208694A (en) | 1988-09-29 |
| EP0130829A2 (en) | 1985-01-09 |
| EP0130829B1 (en) | 1987-06-03 |
| ZA844983B (en) | 1985-02-27 |
| DE3464050D1 (en) | 1987-07-09 |
| JPS60105637A (ja) | 1985-06-11 |
| GR79540B (OSRAM) | 1984-10-30 |
| DK322984A (da) | 1984-12-31 |
| US4644085A (en) | 1987-02-17 |
| NO158376B (no) | 1988-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0641767B1 (en) | Cytotoxic stilbene derivatives and pharmaceutical composition containing them | |
| US5807847A (en) | Nitrate esters | |
| Erhardt et al. | Ultra-short-acting. beta.-adrenergic receptor blocking agents. 1.(Aryloxy) propanolamines containing esters in the nitrogen substituent | |
| IL84515A0 (en) | Rebeccamycin analogs,their production and pharmaceutical compositions containing them | |
| Pernak et al. | Herbicidal ionic liquids derived from renewable sources | |
| PT90214B (pt) | Processo de preparacao de compostos flavonoides substituidos, dos seus sais e de composicoes farmaceuticas que os contem | |
| HU198030B (en) | Process for production of derivatives of benzotiasole and benzotiophen and medical preparatives containing these compounds as active substance | |
| KR830006332A (ko) | 의약품류 제조용 신규의 헤파린 에스테르류 제조방법 | |
| KR840007596A (ko) | 유기인 유도체의염의 제조방법 | |
| US4394389A (en) | Hydroxybenzohydroxamic acids, benzamides and esters as ribonucleotide reductase inhibitors | |
| HU189608B (en) | Process for producing pyridazine derivatives | |
| JPH06505265A (ja) | ヒスタミンｈ↓３受容体に対する作動的または拮抗的活性を有するイミダゾール誘導体 | |
| US4448730A (en) | Hydroxybenzohydroxamic acids, benzamides and esters and related compounds as ribonucleotide reductase inhibitors | |
| Leclerc et al. | Synthesis and. beta.-adrenergic blocking activity of new aliphatic oxime ethers | |
| JP2000511556A (ja) | ２０（ｓ）―カンプトテシンの新規な水溶性ｃ―環類似体 | |
| FI83780C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva (tio) flavener. | |
| US4017628A (en) | Treatment of mange | |
| US4644085A (en) | Rooperol and its derivates | |
| ES8305730A1 (es) | Un procedimiento para la preparacion de un derivado del imidazol. | |
| FI73663C (fi) | Foerfarande foer foerdelning av racematet (1rs,2sr)-2-amino-1-fenylpropan-1-ol i isomerer. | |
| JPS62195384A (ja) | 新規なカンプトテシン誘導体 | |
| PT93675B (pt) | Processo para a preparacao de derivados de acidos aminodicarboxilicos insaturados, contendo fosforo | |
| FI82459B (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva (tio)flavener. | |
| US5756739A (en) | Process for preparing polyamine derivative and intermediates thereof | |
| ES8504188A1 (es) | Un procedimiento para la preparacion de nuevos derivados de dihidronaftiridina. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19941231 |