JPH0369912B2 - - Google Patents
Info
- Publication number
- JPH0369912B2 JPH0369912B2 JP57178210A JP17821082A JPH0369912B2 JP H0369912 B2 JPH0369912 B2 JP H0369912B2 JP 57178210 A JP57178210 A JP 57178210A JP 17821082 A JP17821082 A JP 17821082A JP H0369912 B2 JPH0369912 B2 JP H0369912B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- formula
- acid
- carboxylic acid
- 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
- 150000001875 compounds Chemical class 0.000 claims description 50
- -1 t-butyldimethylsilyl group Chemical group 0.000 claims description 17
- YLWQKYSDNGHLAO-PWRINDRCSA-N bruceolide Chemical class CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](O)C(=O)O[C@@H]4C[C@H]21 YLWQKYSDNGHLAO-PWRINDRCSA-N 0.000 claims description 15
- 150000007934 α,β-unsaturated carboxylic acids Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- ZZZYHIMVKOHVIH-VILODJCFSA-N Brusatol Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)C=C(C)C)C(=O)O[C@@H]4C[C@H]21 ZZZYHIMVKOHVIH-VILODJCFSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- ZZZYHIMVKOHVIH-UHFFFAOYSA-N Brusatol Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(=O)C=C(C)C)C(=O)OC4CC21 ZZZYHIMVKOHVIH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YLWQKYSDNGHLAO-UHFFFAOYSA-N Bruceolide Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(O)C(=O)OC4CC21 YLWQKYSDNGHLAO-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 4
- 238000012746 preparative thin layer chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical compound COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- OIVIDVADCZVCFF-UHFFFAOYSA-N dec-2-enoyl chloride Chemical compound CCCCCCCC=CC(Cl)=O OIVIDVADCZVCFF-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 241001533159 Brucea javanica Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
- YURNCBVQZBJDAJ-AATRIKPKSA-N (E)-hept-2-enoic acid Chemical compound CCCC\C=C\C(O)=O YURNCBVQZBJDAJ-AATRIKPKSA-N 0.000 description 1
- ADLXTJMPCFOTOO-BQYQJAHWSA-N (E)-non-2-enoic acid Chemical compound CCCCCC\C=C\C(O)=O ADLXTJMPCFOTOO-BQYQJAHWSA-N 0.000 description 1
- IBYFOBGPNPINBU-SEYXRHQNSA-N (Z)-tetradec-2-enoic acid Chemical compound CCCCCCCCCCC\C=C/C(O)=O IBYFOBGPNPINBU-SEYXRHQNSA-N 0.000 description 1
- OTTYFDRFBJPGRW-ONEGZZNKSA-N (e)-pent-2-enoyl chloride Chemical compound CC\C=C\C(Cl)=O OTTYFDRFBJPGRW-ONEGZZNKSA-N 0.000 description 1
- YDWODLQEUPYKGJ-MUVFDYEFSA-N 15-O-acetylbruceolide Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@]3(C(=O)OC)[C@@H]5[C@@H](OC(C)=O)C(=O)O[C@@H]4C[C@H]21 YDWODLQEUPYKGJ-MUVFDYEFSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ADLXTJMPCFOTOO-FPLPWBNLSA-N 2-nonenoic acid Chemical compound CCCCCC\C=C/C(O)=O ADLXTJMPCFOTOO-FPLPWBNLSA-N 0.000 description 1
- NIONDZDPPYHYKY-PLNGDYQASA-N 2Z-Hexenoic acid Chemical compound CCC\C=C/C(O)=O NIONDZDPPYHYKY-PLNGDYQASA-N 0.000 description 1
- CHOGNBXWAZDZBM-UHFFFAOYSA-N 4-(aminomethyl)benzenecarboximidamide Chemical compound NCC1=CC=C(C(N)=N)C=C1 CHOGNBXWAZDZBM-UHFFFAOYSA-N 0.000 description 1
- 241000589155 Agrobacterium tumefaciens Species 0.000 description 1
- 241000848171 Brucea antidysenterica Species 0.000 description 1
- IRQXZTBHNKVIRL-GOTQHHPNSA-N Bruceantin Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)\C=C(/C)C(C)C)C(=O)O[C@@H]4C[C@H]21 IRQXZTBHNKVIRL-GOTQHHPNSA-N 0.000 description 1
- ZBXITHPYBBXZRG-QYUWQHSUSA-N Brucein E Natural products O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)[C@H](O)[C@@H](O)C=C(C)[C@@H]3C[C@@H]3[C@]22CO[C@@]1(C)[C@]2(O)[C@@H](O)C(=O)O3 ZBXITHPYBBXZRG-QYUWQHSUSA-N 0.000 description 1
- ZBXITHPYBBXZRG-UHFFFAOYSA-N Bruceine E Natural products OC1C(O)C2C3(C)C(O)C(O)C=C(C)C3CC3C22COC1(C)C2(O)C(O)C(=O)O3 ZBXITHPYBBXZRG-UHFFFAOYSA-N 0.000 description 1
- AKSGLPBROCFVSE-TUHDNREHSA-N Bruceoside A Chemical compound O=C([C@@H](C)[C@@H]1C[C@H]2OC(=O)[C@H](OC(=O)C=C(C)C)[C@@H]3[C@]22CO[C@@]3([C@H]([C@H](O)[C@@H]2[C@@]1(C)C=1)O)C(=O)OC)C=1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O AKSGLPBROCFVSE-TUHDNREHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- IRQXZTBHNKVIRL-UHFFFAOYSA-N NSC 165563 Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(=O)C=C(C)C(C)C)C(=O)OC4CC21 IRQXZTBHNKVIRL-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 235000010889 Rhus javanica Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NDAUQCCKCKVGJF-UHFFFAOYSA-N ac1l7r1d Chemical compound CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(=O)CC(C)C(C)C)C(=O)OC4CC21 NDAUQCCKCKVGJF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- NWMHBMQWRKWPLK-UHFFFAOYSA-N bruceantarin Natural products COC(=O)C12OCC34C(CC5C(=C(O)C(=O)CC5(C)C3C(O)C1O)C)CC(=O)C(OC(=O)c6ccccc6)C24 NWMHBMQWRKWPLK-UHFFFAOYSA-N 0.000 description 1
- IRQXZTBHNKVIRL-AYXPYFKUSA-N bruceantin Natural products CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)C=C(C)C(C)C)C(=O)O[C@@H]4C[C@H]21 IRQXZTBHNKVIRL-AYXPYFKUSA-N 0.000 description 1
- YDWODLQEUPYKGJ-UHFFFAOYSA-N brucein B Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(C)=O)C(=O)OC4CC21 YDWODLQEUPYKGJ-UHFFFAOYSA-N 0.000 description 1
- JBDMZGKDLMGOFR-KQSRGDCESA-N bruceine D Chemical compound O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)[C@H](O)C(=O)C=C(C)[C@@H]3C[C@@H]3[C@]22CO[C@@]1(C)[C@]2(O)[C@@H](O)C(=O)O3 JBDMZGKDLMGOFR-KQSRGDCESA-N 0.000 description 1
- ZBXITHPYBBXZRG-ZOKABGNJSA-N bruceine e Chemical compound O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)[C@H](O)[C@@H](O)C=C(C)[C@@H]3C[C@@H]3[C@]22CO[C@]1(C)[C@]2(O)[C@@H](O)C(=O)O3 ZBXITHPYBBXZRG-ZOKABGNJSA-N 0.000 description 1
- JBDMZGKDLMGOFR-CABQPPGUSA-N bruceine-D Natural products O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)[C@@H](O)C(=O)C=C(C)[C@@H]3C[C@@H]3[C@]22CO[C@@]1(C)[C@]2(O)[C@@H](O)C(=O)O3 JBDMZGKDLMGOFR-CABQPPGUSA-N 0.000 description 1
- ASHBUMOFZXVPPC-IATOJABCSA-N bruceoside A Natural products COC(=O)[C@@]12OC[C@@]34[C@@H](C[C@H]5[C@H](C)C(=O)C(=C[C@]5(C)[C@H]3[C@@H](O)[C@@H]1O)O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)OC(=O)[C@H](OC(=O)C=C(C)C(C)C)[C@@H]24 ASHBUMOFZXVPPC-IATOJABCSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WXBXVVIUZANZAU-HJWRWDBZSA-N cis-2-decenoic acid Chemical compound CCCCCCC\C=C/C(O)=O WXBXVVIUZANZAU-HJWRWDBZSA-N 0.000 description 1
- PAWGRNGPMLVJQH-KHPPLWFESA-N cis-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C/C(O)=O PAWGRNGPMLVJQH-KHPPLWFESA-N 0.000 description 1
- YURNCBVQZBJDAJ-WAYWQWQTSA-N cis-2-heptenoic acid Chemical compound CCCC\C=C/C(O)=O YURNCBVQZBJDAJ-WAYWQWQTSA-N 0.000 description 1
- CWMPPVPFLSZGCY-SREVYHEPSA-N cis-alpha-octenoic acid Chemical compound CCCCC\C=C/C(O)=O CWMPPVPFLSZGCY-SREVYHEPSA-N 0.000 description 1
- LKOVPWSSZFDYPG-MSUUIHNZSA-N cis-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C/C(O)=O LKOVPWSSZFDYPG-MSUUIHNZSA-N 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- YIYBQIKDCADOSF-ARJAWSKDSA-N cis-pent-2-enoic acid Chemical compound CC\C=C/C(O)=O YIYBQIKDCADOSF-ARJAWSKDSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- REDBNPUNYZYECN-UHFFFAOYSA-N hept-2-enoyl chloride Chemical compound CCCCC=CC(Cl)=O REDBNPUNYZYECN-UHFFFAOYSA-N 0.000 description 1
- NVXGQRPGUGAMNJ-UHFFFAOYSA-N hex-2-enoyl chloride Chemical compound CCCC=CC(Cl)=O NVXGQRPGUGAMNJ-UHFFFAOYSA-N 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- SUHXRRRGYUULBU-UHFFFAOYSA-N oct-2-enoyl chloride Chemical compound CCCCCC=CC(Cl)=O SUHXRRRGYUULBU-UHFFFAOYSA-N 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- PAWGRNGPMLVJQH-ZHACJKMWSA-N trans-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C\C(O)=O PAWGRNGPMLVJQH-ZHACJKMWSA-N 0.000 description 1
- IBYFOBGPNPINBU-OUKQBFOZSA-N trans-2-tetradecenoic acid Chemical compound CCCCCCCCCCC\C=C\C(O)=O IBYFOBGPNPINBU-OUKQBFOZSA-N 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- UDKADNQGYPJTHY-UHFFFAOYSA-N tridec-2-enoyl chloride Chemical compound CCCCCCCCCCC=CC(Cl)=O UDKADNQGYPJTHY-UHFFFAOYSA-N 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57178210A JPS5967287A (ja) | 1982-10-09 | 1982-10-09 | 新規プルセオライド誘導体及びその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57178210A JPS5967287A (ja) | 1982-10-09 | 1982-10-09 | 新規プルセオライド誘導体及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5967287A JPS5967287A (ja) | 1984-04-16 |
| JPH0369912B2 true JPH0369912B2 (ko) | 1991-11-05 |
Family
ID=16044501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57178210A Granted JPS5967287A (ja) | 1982-10-09 | 1982-10-09 | 新規プルセオライド誘導体及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5967287A (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002062334A2 (en) * | 2001-02-05 | 2002-08-15 | Pezzuto John M | Cancer chemopreventative compounds and compositions and methods of treating cancers |
| CN109776565B (zh) * | 2019-01-28 | 2020-06-16 | 浙江省中医药研究院 | 一种苦味素类化合物及其制备方法与应用 |
| CN113024551B (zh) * | 2021-05-20 | 2021-08-06 | 江西中医药大学 | 一种从鸦胆子中提取分离的化合物及其制备方法和应用 |
-
1982
- 1982-10-09 JP JP57178210A patent/JPS5967287A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5967287A (ja) | 1984-04-16 |
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