GB1570082A - Polycyclic quinonoid antibiotics - Google Patents
Polycyclic quinonoid antibiotics Download PDFInfo
- Publication number
- GB1570082A GB1570082A GB47846/76A GB4784676A GB1570082A GB 1570082 A GB1570082 A GB 1570082A GB 47846/76 A GB47846/76 A GB 47846/76A GB 4784676 A GB4784676 A GB 4784676A GB 1570082 A GB1570082 A GB 1570082A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- compound
- suitably
- reaction
- mixture
- Prior art date
- 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.)
- Expired
Links
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- 229940088710 antibiotic agent Drugs 0.000 title description 3
- 125000003367 polycyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- -1 quinizarinquinone compound Chemical class 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical class C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
- 239000011707 mineral Substances 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- YOFDHOWPGULAQF-UHFFFAOYSA-N Daunomycin-Aglycone Natural products C1C(O)(C(C)=O)CC(O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 8
- 230000003301 hydrolyzing effect Effects 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 230000000887 hydrating effect Effects 0.000 claims description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 36
- 239000000243 solution Substances 0.000 claims 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 33
- 239000002904 solvent Substances 0.000 claims 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 29
- 229940022663 acetate Drugs 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 15
- 239000003960 organic solvent Substances 0.000 claims 15
- YHBWDDDQUUPGJJ-UHFFFAOYSA-N 9-ethynyl-6,9,11-trihydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1CC(O)(C#C)CCC1=C2O YHBWDDDQUUPGJJ-UHFFFAOYSA-N 0.000 claims 13
- WPHDSJQYRCDRDV-UHFFFAOYSA-N 1-acetyl-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione Chemical compound C(C)(=O)C1=CC=CC=2C(C3=C(C=4CCC(CC4C(=C3C(C12)=O)O)O)O)=O WPHDSJQYRCDRDV-UHFFFAOYSA-N 0.000 claims 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 12
- 229960000583 acetic acid Drugs 0.000 claims 12
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 12
- 239000002244 precipitate Substances 0.000 claims 12
- 239000011541 reaction mixture Substances 0.000 claims 12
- 239000007787 solid Substances 0.000 claims 12
- MORCGAGNSSORNZ-UHFFFAOYSA-N 5,12-dihydroxy-3,4-dihydro-1h-tetracene-2,6,11-trione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1CC(=O)CCC1=C2O MORCGAGNSSORNZ-UHFFFAOYSA-N 0.000 claims 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 10
- 239000000284 extract Substances 0.000 claims 10
- 239000000047 product Substances 0.000 claims 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 235000010755 mineral Nutrition 0.000 claims 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 8
- 125000001743 benzylic group Chemical group 0.000 claims 8
- 239000007858 starting material Substances 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 8
- 125000001033 ether group Chemical group 0.000 claims 7
- 239000007800 oxidant agent Substances 0.000 claims 7
- ZUFQFGSMHXKORU-UHFFFAOYSA-N 9-acetyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(O)CC(C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-UHFFFAOYSA-N 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- 239000007818 Grignard reagent Substances 0.000 claims 6
- KNCZUXHSQJQWIB-UHFFFAOYSA-N anthracene-1,4,9,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(=O)C=CC2=O KNCZUXHSQJQWIB-UHFFFAOYSA-N 0.000 claims 6
- 238000004587 chromatography analysis Methods 0.000 claims 6
- 150000008282 halocarbons Chemical class 0.000 claims 6
- 239000000725 suspension Substances 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 5
- 238000010828 elution Methods 0.000 claims 5
- 238000001914 filtration Methods 0.000 claims 5
- 239000000463 material Substances 0.000 claims 5
- 230000003647 oxidation Effects 0.000 claims 5
- 238000007254 oxidation reaction Methods 0.000 claims 5
- 239000003495 polar organic solvent Substances 0.000 claims 5
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 5
- 235000011152 sodium sulphate Nutrition 0.000 claims 5
- 238000003756 stirring Methods 0.000 claims 5
- 239000001117 sulphuric acid Substances 0.000 claims 5
- 235000011149 sulphuric acid Nutrition 0.000 claims 5
- HWHFKYJAAJPFQF-UHFFFAOYSA-N 1,4-dimethoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(OC)=CC=C2OC HWHFKYJAAJPFQF-UHFFFAOYSA-N 0.000 claims 4
- NNQPXACEWVDHMS-UHFFFAOYSA-N 6,8,11-trihydroxy-7,10-dihydrotetracene-5,12-dione Chemical compound OC1=C2C(C=3C=CC=CC3C(C2=C(C=2CC(=CCC12)O)O)=O)=O NNQPXACEWVDHMS-UHFFFAOYSA-N 0.000 claims 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 4
- 125000000746 allylic group Chemical group 0.000 claims 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 4
- 239000002026 chloroform extract Substances 0.000 claims 4
- 235000019439 ethyl acetate Nutrition 0.000 claims 4
- 230000007062 hydrolysis Effects 0.000 claims 4
- 238000006460 hydrolysis reaction Methods 0.000 claims 4
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims 4
- 235000006408 oxalic acid Nutrition 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000000377 silicon dioxide Substances 0.000 claims 4
- ZUFQFGSMHXKORU-YUNKPMOVSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-YUNKPMOVSA-N 0.000 claims 3
- HIWASLYFYGJESA-UHFFFAOYSA-N 6,9,11-trihydroxy-2,3-dimethyl-7,8-dihydrotetracene-5,12-dione Chemical compound C1CC(O)=CC2=C1C(O)=C1C(=O)C(C=C(C(=C3)C)C)=C3C(=O)C1=C2O HIWASLYFYGJESA-UHFFFAOYSA-N 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 3
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 238000013019 agitation Methods 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 230000031709 bromination Effects 0.000 claims 3
- 238000005893 bromination reaction Methods 0.000 claims 3
- PMOLKBNSJNLKGB-UHFFFAOYSA-N buta-1,3-dien-2-yl acetate Chemical compound CC(=O)OC(=C)C=C PMOLKBNSJNLKGB-UHFFFAOYSA-N 0.000 claims 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 3
- 239000012362 glacial acetic acid Substances 0.000 claims 3
- 150000004795 grignard reagents Chemical class 0.000 claims 3
- 239000011261 inert gas Substances 0.000 claims 3
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims 3
- 238000000746 purification Methods 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 claims 2
- WCXKKSLEUONKJB-UHFFFAOYSA-N 1,4-dihydroxy-5,8-dimethoxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(OC)=CC=C2OC WCXKKSLEUONKJB-UHFFFAOYSA-N 0.000 claims 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 2
- BJLPSIPGXQUFGQ-UHFFFAOYSA-N 2-(2,5-dimethoxybenzoyl)benzoic acid Chemical compound COC1=CC=C(OC)C(C(=O)C=2C(=CC=CC=2)C(O)=O)=C1 BJLPSIPGXQUFGQ-UHFFFAOYSA-N 0.000 claims 2
- POZBTXRBEALEDF-UHFFFAOYSA-N 5,12-dihydroxy-7,10-dimethoxy-3,4-dihydro-1h-tetracene-2,6,11-trione Chemical compound C1C(=O)CCC2=C1C(O)=C1C(=O)C(C(OC)=CC=C3OC)=C3C(=O)C1=C2O POZBTXRBEALEDF-UHFFFAOYSA-N 0.000 claims 2
- CNKYUJHZRCNCHY-UHFFFAOYSA-N 5,12-dihydroxy-8,9-dimethyl-3h-tetracene-2,6,11-trione Chemical compound C1C(=O)C=C2C(O)=C(C(=O)C3=C(C=C(C(=C3)C)C)C3=O)C3=C(O)C2=C1 CNKYUJHZRCNCHY-UHFFFAOYSA-N 0.000 claims 2
- CMNFGMRKUMTLDW-UHFFFAOYSA-N 5,8-dimethoxyanthracene-1,4,9,10-tetrone Chemical compound COC1=CC=C(OC)C(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O CMNFGMRKUMTLDW-UHFFFAOYSA-N 0.000 claims 2
- BRHPCPPFSBACMJ-UHFFFAOYSA-N 6,7-dimethylanthracene-1,4,9,10-tetrone Chemical compound C1=C(C)C(C)=CC(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O BRHPCPPFSBACMJ-UHFFFAOYSA-N 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims 2
- 239000012298 atmosphere Substances 0.000 claims 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 230000005587 bubbling Effects 0.000 claims 2
- LNDKRVOOYMEYTC-UHFFFAOYSA-N buta-1,3-dien-1-ol Chemical compound OC=CC=C LNDKRVOOYMEYTC-UHFFFAOYSA-N 0.000 claims 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 claims 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 2
- 238000007872 degassing Methods 0.000 claims 2
- 238000005837 enolization reaction Methods 0.000 claims 2
- 238000006345 epimerization reaction Methods 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- ANQVKHGDALCPFZ-UHFFFAOYSA-N ethyl 2-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]acetate Chemical compound C1=C2NC(CC(=O)OCC)=NC2=CC=C1N1CCN(C)CC1 ANQVKHGDALCPFZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 2
- 229940101209 mercuric oxide Drugs 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims 2
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 claims 2
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 claims 2
- 239000002002 slurry Substances 0.000 claims 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 claims 2
- 229940070710 valerate Drugs 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- 238000010792 warming Methods 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- AMKRBKSZCGCEJK-UHFFFAOYSA-N 1,2-dimethoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(OC)C(OC)=CC=C3C(=O)C2=C1 AMKRBKSZCGCEJK-UHFFFAOYSA-N 0.000 claims 1
- GNRPVZNNVOGXHD-UHFFFAOYSA-N 1,2-dimethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(C)C(C)=CC=C3C(=O)C2=C1 GNRPVZNNVOGXHD-UHFFFAOYSA-N 0.000 claims 1
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 claims 1
- ZCRXXBBYNKRCGS-UHFFFAOYSA-N 1,4,5,8-tetramethoxyanthracene-9,10-dione Chemical compound O=C1C2=C(OC)C=CC(OC)=C2C(=O)C2=C1C(OC)=CC=C2OC ZCRXXBBYNKRCGS-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- VXVFPBBTNGMJFI-UHFFFAOYSA-N 1,4-dihydrotetracene-5,6,11,12-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C(C2=O)=C1C(=O)C1=C2CC=CC1 VXVFPBBTNGMJFI-UHFFFAOYSA-N 0.000 claims 1
- ZRFDDEAGCRNVNI-UHFFFAOYSA-N 1,4-dimethoxy-6,7-dimethylanthracene-9,10-dione Chemical compound O=C1C2=CC(C)=C(C)C=C2C(=O)C2=C1C(OC)=CC=C2OC ZRFDDEAGCRNVNI-UHFFFAOYSA-N 0.000 claims 1
- SJHHHHHQWQOCDQ-UHFFFAOYSA-N 1,8-diamino-4,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC(N)=C2C(=O)C2=C1C(O)=CC=C2N SJHHHHHQWQOCDQ-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- VLXYMWIODHEZLX-UHFFFAOYSA-N 2-(2,5-dihydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC(O)=CC=C1O VLXYMWIODHEZLX-UHFFFAOYSA-N 0.000 claims 1
- DIFFKPZRWQZVNX-UHFFFAOYSA-N 2-(2,5-dimethoxybenzoyl)-4,5-dimethylbenzoic acid Chemical compound COC1=C(C(=O)C2=C(C(=O)O)C=C(C(=C2)C)C)C=C(C=C1)OC DIFFKPZRWQZVNX-UHFFFAOYSA-N 0.000 claims 1
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- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 claims 1
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 claims 1
- BLFCXYJTVFTNRX-UHFFFAOYSA-N 2-chloro-4-(furan-2-yl)pyrimidine Chemical compound ClC1=NC=CC(C=2OC=CC=2)=N1 BLFCXYJTVFTNRX-UHFFFAOYSA-N 0.000 claims 1
- YWYDMGWSJOUTDI-UHFFFAOYSA-N 4,7-dihydroxy-2-benzofuran-1,3-dione Chemical compound OC1=CC=C(O)C2=C1C(=O)OC2=O YWYDMGWSJOUTDI-UHFFFAOYSA-N 0.000 claims 1
- WEPCDISQBQXOBE-UHFFFAOYSA-N 4,7-dimethyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=C(C)C2=C1C(=O)OC2=O WEPCDISQBQXOBE-UHFFFAOYSA-N 0.000 claims 1
- CCTOEAMRIIXGDJ-UHFFFAOYSA-N 4-hydroxy-2-benzofuran-1,3-dione Chemical compound OC1=CC=CC2=C1C(=O)OC2=O CCTOEAMRIIXGDJ-UHFFFAOYSA-N 0.000 claims 1
- CMQYISATYUYSAC-UHFFFAOYSA-N 5,6-dimethyl-2-benzofuran-1,3-dione Chemical compound C1=C(C)C(C)=CC2=C1C(=O)OC2=O CMQYISATYUYSAC-UHFFFAOYSA-N 0.000 claims 1
- SZKHVFQMYPOBPL-UHFFFAOYSA-N 5,8-dimethylanthracene-1,4,9,10-tetrone Chemical compound CC1=CC=C(C)C(C2=O)=C1C(=O)C1=C2C(=O)C=CC1=O SZKHVFQMYPOBPL-UHFFFAOYSA-N 0.000 claims 1
- MGHGIFGQJWUVCO-UHFFFAOYSA-N 6,8,11-trihydroxy-1,4-dimethoxy-7,10-dihydrotetracene-5,12-dione Chemical compound COC1=CC=C(C=2C(C3=C(C=4CC=C(CC4C(=C3C(C12)=O)O)O)O)=O)OC MGHGIFGQJWUVCO-UHFFFAOYSA-N 0.000 claims 1
- DAPXLMCDFUBZJS-UHFFFAOYSA-N 6,8,11-trihydroxy-2,3-dimethyltetracene-5,12-dione Chemical compound CC1=CC=2C(C3=C(C4=CC(=CC=C4C(=C3C(C=2C=C1C)=O)O)O)O)=O DAPXLMCDFUBZJS-UHFFFAOYSA-N 0.000 claims 1
- NVFZNZASROGHQA-UHFFFAOYSA-N 6,8,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1CCC(O)CC1=C2O NVFZNZASROGHQA-UHFFFAOYSA-N 0.000 claims 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- 238000006418 Brown reaction Methods 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- 101100011794 Caenorhabditis elegans epi-1 gene Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- KGSLNPXZUSXXIJ-UHFFFAOYSA-N OC1=C(C=2C(C=3C(C4=CC=CC=C4C(C3C(C2C=C1)=O)=O)=O)=O)O Chemical compound OC1=C(C=2C(C=3C(C4=CC=CC=C4C(C3C(C2C=C1)=O)=O)=O)=O)O KGSLNPXZUSXXIJ-UHFFFAOYSA-N 0.000 claims 1
- VONGZNXBKCOUHB-UHFFFAOYSA-N Phenylmethyl butanoate Chemical compound CCCC(=O)OCC1=CC=CC=C1 VONGZNXBKCOUHB-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical group 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000005899 aromatization reaction Methods 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 229940007550 benzyl acetate Drugs 0.000 claims 1
- 239000012267 brine Substances 0.000 claims 1
- LLRUDMQDJFCPRE-UHFFFAOYSA-N buta-1,3-dienyl benzoate Chemical compound C=CC=COC(=O)C1=CC=CC=C1 LLRUDMQDJFCPRE-UHFFFAOYSA-N 0.000 claims 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000001722 carbon compounds Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- 229940076286 cupric acetate Drugs 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 229960004132 diethyl ether Drugs 0.000 claims 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
- 230000008034 disappearance Effects 0.000 claims 1
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- 238000003379 elimination reaction Methods 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- 239000012259 ether extract Substances 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 239000002024 ethyl acetate extract Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000011010 flushing procedure Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000003365 glass fiber Substances 0.000 claims 1
- 238000005858 glycosidation reaction Methods 0.000 claims 1
- 229930182470 glycoside Natural products 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910001385 heavy metal Inorganic materials 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 150000004715 keto acids Chemical class 0.000 claims 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
- 229960001156 mitoxantrone Drugs 0.000 claims 1
- 239000004570 mortar (masonry) Substances 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 239000012457 nonaqueous media Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical class CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 claims 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims 1
- 125000004151 quinonyl group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 229910001923 silver oxide Inorganic materials 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 238000000527 sonication Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 claims 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
- 229960000975 daunorubicin Drugs 0.000 description 2
- 229940009456 adriamycin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/632,939 US4070382A (en) | 1975-11-18 | 1975-11-18 | Intermediates for polycyclic quinoid antibiotics |
| US05/673,513 US4021457A (en) | 1975-11-18 | 1976-04-05 | Intermediates for polycyclic quinonoid antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1570082A true GB1570082A (en) | 1980-06-25 |
Family
ID=27091763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47846/76A Expired GB1570082A (en) | 1975-11-18 | 1976-11-17 | Polycyclic quinonoid antibiotics |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4021457A (enExample) |
| DD (1) | DD130575A5 (enExample) |
| DE (1) | DE2651201A1 (enExample) |
| FR (1) | FR2360549A1 (enExample) |
| GB (1) | GB1570082A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089872A (en) * | 1977-03-09 | 1978-05-16 | The Upjohn Company | Antibiotics steffimycinol and 7-deoxysteffimycinol and process for preparing the same |
| US4196127A (en) * | 1978-06-01 | 1980-04-01 | Research Corporation | Anthracyclines |
| US4244880A (en) * | 1978-06-05 | 1981-01-13 | University Of Kansas Endowment Association | Anthracycline synthesis |
| US4164503A (en) * | 1978-10-10 | 1979-08-14 | Research Corporation | Quinonoid intermediates from chloroprene |
| US4405522A (en) * | 1982-01-18 | 1983-09-20 | Adria Laboratories Inc. | Anthracycline synthesis |
| BE896743A (fr) * | 1982-08-13 | 1983-09-16 | Erba Farmitalia | Synthese de naphtacenequinone. |
| GB8708927D0 (en) * | 1987-04-14 | 1987-05-20 | Erba Farmitalia | Chiral synthesis of anthracyclines |
| NZ224252A (en) * | 1987-04-21 | 1991-09-25 | Erba Carlo Spa | An anthracycline glycoside and its preparation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2922691A (en) * | 1955-08-02 | 1960-01-26 | Ciba Ltd | Anthraquinone dyes and polyethylene terephthalate fibers dyed therewith |
| CH350396A (de) * | 1956-07-17 | 1960-11-30 | Ciba Geigy | Verfahren zur Herstellung neuer Farbstoffe der Anthrachinonreihe |
| CH470334A (de) * | 1965-01-14 | 1969-03-31 | Sandoz Ag | Verfahren zur Herstellung von polycyclischen chinoiden Verbindungen |
| CH514530A (de) * | 1965-01-15 | 1971-10-31 | Sandoz Ag | Verfahren zur Herstellung von polycyclischen chinoiden Verbindungen |
| FR7785M (enExample) * | 1968-10-07 | 1970-03-23 | ||
| GB1357985A (en) * | 1972-02-18 | 1974-06-26 | Ici Ltd | Anthraquinone compounds |
-
1976
- 1976-04-05 US US05/673,513 patent/US4021457A/en not_active Expired - Lifetime
- 1976-11-10 DE DE19762651201 patent/DE2651201A1/de not_active Ceased
- 1976-11-17 FR FR7634663A patent/FR2360549A1/fr active Granted
- 1976-11-17 GB GB47846/76A patent/GB1570082A/en not_active Expired
- 1976-11-17 DD DD7600195825A patent/DD130575A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD130575A5 (de) | 1978-04-12 |
| DE2651201A1 (de) | 1977-06-02 |
| FR2360549B1 (enExample) | 1980-12-05 |
| US4021457A (en) | 1977-05-03 |
| FR2360549A1 (fr) | 1978-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |