GB1063255A - The antibiotic anguidine and derivatives thereof - Google Patents
The antibiotic anguidine and derivatives thereofInfo
- Publication number
- GB1063255A GB1063255A GB36864/63A GB3686463A GB1063255A GB 1063255 A GB1063255 A GB 1063255A GB 36864/63 A GB36864/63 A GB 36864/63A GB 3686463 A GB3686463 A GB 3686463A GB 1063255 A GB1063255 A GB 1063255A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anguidine
- acyl
- monodesacetyl
- anguidol
- dihydro
- 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
- AUGQEEXBDZWUJY-UHFFFAOYSA-N Diacetoxyscirpenol Natural products CC(=O)OCC12CCC(C)=CC1OC1C(O)C(OC(C)=O)C2(C)C11CO1 AUGQEEXBDZWUJY-UHFFFAOYSA-N 0.000 title abstract 16
- AUGQEEXBDZWUJY-ZLJUKNTDSA-N Diacetoxyscirpenol Chemical compound C([C@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@@H]1C=C(C)CC[C@@]13COC(=O)C)O2 AUGQEEXBDZWUJY-ZLJUKNTDSA-N 0.000 title abstract 15
- 230000003115 biocidal effect Effects 0.000 title abstract 2
- PXEBOIUZEXXBGH-UHFFFAOYSA-N scirpenetriol Natural products OCC12CCC(C)=CC1OC1C(O)C(O)C2(C)C11CO1 PXEBOIUZEXXBGH-UHFFFAOYSA-N 0.000 abstract 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- -1 acyl anguidine Chemical compound 0.000 abstract 2
- RSXUHWPVLJXTGJ-ZUAMBHNYSA-N dihydroanguidine Chemical compound C([C@]12[C@@]3(C)[C@@H](OC(C)=O)[C@H](O)[C@@H]1OC1C3(COC(C)=O)CCC(C1)C)O2 RSXUHWPVLJXTGJ-ZUAMBHNYSA-N 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 241000223218 Fusarium Species 0.000 abstract 1
- 241000221779 Fusarium sambucinum Species 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- JXEGMONJOSAULB-PHGZOOGPSA-N [(3as,5r,5as,6s,8r,8as,9s,9ar)-9-acetyloxy-8-hydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3ah-azuleno[6,5-b]furan-6-yl] acetate Chemical compound C[C@@H]1C[C@@H]2OC(=O)C(=C)[C@H]2[C@H](OC(C)=O)[C@]2(C)[C@H](O)C[C@H](OC(C)=O)[C@@H]12 JXEGMONJOSAULB-PHGZOOGPSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000015097 nutrients Nutrition 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 abstract 1
- 235000015497 potassium bicarbonate Nutrition 0.000 abstract 1
- 239000011736 potassium bicarbonate Substances 0.000 abstract 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 abstract 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G11/00—Antibiotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/145—Fungal isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
- C12R2001/77—Fusarium
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Engineering & Computer Science (AREA)
- Botany (AREA)
- Mycology (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
<PICT:1063255/C2/1> An anti-tumour antibiotic anguidine and/or monodesacetyl anguidine are produced by cultivating Fusarium anguiodes Sherb NRRL 3020 or Fusarium sambucinum ATCC 11852 in an aqueous nutrient solution and the antibiotics are obtained from the clarified broth by extraction or adsorption. Extraction may be by means of ethyl acetate, followed by treating the residue with petroleum ether-aqueous methanol and chromatography of the methanol-water phase on silica gel. Anguidine has a melting point of 162-164 DEG C.; <FORM:1063255/C2/1> (C=1.28 in chloroform), contains 62.1% C, 7.1% H and 30.3% O, i.e. C19H26O7; mol. wt. 359; absorptio in U.V. at 192.5 mm (log e =4.02); I.R. as in Fig. 1; soluble in acetone, ethanol, dioxane, chloroform, methylene chloride, pyridine, toluene, soluble with difficulty in water, diethyl ether, diisopropyl ether, pentane, hexane and heptane. Anguidine is di-O-acetyl anguidol and anguidol is a trihydroxy heterocyclic compound. Anguidol is prepared by the hydrolysis with an alkali metal hydroxide or an alkaline earth metal hydroxide of anguidine, monodesacetyl anguidine or acyl anguidine. Monodesacetyl anguidine is obtained by treating anguidine or an acyl anguidine with aqueous methanolic potassium hydrogen carbonate solution, acyl anguidines, acyl dihydro anguidines, acyl anguidols and acyl monodesacetyl-anguidine are produced by acylation, e.g. with acid halide of anguidine, anguidol, dihydro anguidine or monodesacetyl anguidine respectively. Dihydro anguidine is produced by the catalytic hydrogenation of anguidine. Anguidine is active against tumours and fungi. Pharmaceutical compositions for oral, parenteral or topical administration comprise a carrier and anguidine or an anguidine derivative as mentioned above.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1142362A CH428097A (en) | 1962-09-27 | 1962-09-27 | Process for making new antibiotics |
| CH1095663A CH461706A (en) | 1962-09-27 | 1963-09-05 | Process for the manufacture of a new antibiotic |
| CH1095763 | 1963-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1063255A true GB1063255A (en) | 1967-03-30 |
Family
ID=27176529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36864/63A Expired GB1063255A (en) | 1962-09-27 | 1963-09-19 | The antibiotic anguidine and derivatives thereof |
Country Status (6)
| Country | Link |
|---|---|
| DK (1) | DK112093B (en) |
| ES (1) | ES292009A1 (en) |
| FR (1) | FR3702M (en) |
| GB (1) | GB1063255A (en) |
| LU (1) | LU44501A1 (en) |
| OA (1) | OA00711A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4284568A (en) * | 1980-04-04 | 1981-08-18 | Bristol-Myers Company | Antitumor agents |
| US4332732A (en) * | 1980-04-04 | 1982-06-01 | Bristol-Myers Company | Antitumor agents |
| US4332951A (en) * | 1979-11-19 | 1982-06-01 | Bristol-Myers Company | Antitumor agents |
| US4352936A (en) * | 1979-07-27 | 1982-10-05 | Bristol-Myers Company | Antitumor agents |
| US4413134A (en) * | 1981-03-04 | 1983-11-01 | Bristol-Myers Company | Triacylated derivative of scirpentriol |
| US4433158A (en) * | 1981-01-09 | 1984-02-21 | Bristol-Myers Company | 3-Hydroxyiminoscirpen-4β, 15-diol esters useful as antitumor agents |
| US4456765A (en) * | 1980-04-04 | 1984-06-26 | Bristol-Myers Company | Trichothec-9-ene-3,4,15-triol,12,13-epoxy-3-chloroacetate useful as an anti-tumor agent |
| US4552971A (en) * | 1980-04-04 | 1985-11-12 | Bristol-Myers Company | 3α,15-Bis(chloroacetoxy)-4.beta.-hydroxy-12,13-epoxytrichothec-9-ene useful as an antitumor agent |
-
1963
- 1963-09-19 GB GB36864/63A patent/GB1063255A/en not_active Expired
- 1963-09-25 LU LU44501D patent/LU44501A1/xx unknown
- 1963-09-26 ES ES0292009A patent/ES292009A1/en not_active Expired
- 1963-12-23 FR FR958232A patent/FR3702M/en active Active
-
1964
- 1964-11-10 DK DK554764AA patent/DK112093B/en unknown
- 1964-12-08 OA OA50770A patent/OA00711A/en unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4352936A (en) * | 1979-07-27 | 1982-10-05 | Bristol-Myers Company | Antitumor agents |
| US4332951A (en) * | 1979-11-19 | 1982-06-01 | Bristol-Myers Company | Antitumor agents |
| US4284568A (en) * | 1980-04-04 | 1981-08-18 | Bristol-Myers Company | Antitumor agents |
| US4332732A (en) * | 1980-04-04 | 1982-06-01 | Bristol-Myers Company | Antitumor agents |
| US4456765A (en) * | 1980-04-04 | 1984-06-26 | Bristol-Myers Company | Trichothec-9-ene-3,4,15-triol,12,13-epoxy-3-chloroacetate useful as an anti-tumor agent |
| US4552971A (en) * | 1980-04-04 | 1985-11-12 | Bristol-Myers Company | 3α,15-Bis(chloroacetoxy)-4.beta.-hydroxy-12,13-epoxytrichothec-9-ene useful as an antitumor agent |
| US4433158A (en) * | 1981-01-09 | 1984-02-21 | Bristol-Myers Company | 3-Hydroxyiminoscirpen-4β, 15-diol esters useful as antitumor agents |
| US4413134A (en) * | 1981-03-04 | 1983-11-01 | Bristol-Myers Company | Triacylated derivative of scirpentriol |
Also Published As
| Publication number | Publication date |
|---|---|
| DK112093B (en) | 1968-11-11 |
| LU44501A1 (en) | 1964-03-25 |
| ES292009A1 (en) | 1965-01-01 |
| FR3702M (en) | 1965-11-22 |
| OA00711A (en) | 1967-07-15 |
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