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| Item type: | Patent | ||||||
|---|---|---|---|---|---|---|---|
| Number of Pages: | 11 | ||||||
| Date: | 1987 | ||||||
| Additional Information (public): | CAN 107:96423 25-2 Benzene, Its Derivatives, and Condensed Benzenoid Compounds Patent 19870507 103-80-0 (Phenylacetylchloride) Role: RCT (Reactant), RACT (Reactant or reagent) (Friedel-Crafts acylation by, of anisole); 100-66-3 (Anisole) Role: RCT (Reactant), RACT (Reactant or reagent) (Friedel-Crafts acylation of); 104-92-7 (4-Bromoanisole); 36603-49-3 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with phenylbutenone deriv.); 4390-94-7; 78423-10-6 Role: RCT (Reactant), RACT (Reactant or reagent) (arylation of, by Grignard reagent); 625-36-5 (beta -Chloropropionyl chloride); 15486-96-1 (beta -Bromopropionyl chloride) Role: RCT (Reactant), RACT (Reactant or reagent) (esterification by, of (hydroxyphenyl)butene deriv.); 1023-17-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and alkylation of, by Et iodide); 110008-70-3P; 110008-72-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and esterification of, by carbamoyl chloride deriv.); 82333-56-0P; 110008-71-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and ether cleavage of); 91221-46-4P; 110008-57-6P; 110008-58-7P; 110008-59-8P; 110008-60-1P; 110008-61-2P; 110008-62-3P; 110008-63-4P; 110008-64-5P; 110008-65-6P; 110008-66-7P; 110008-67-8P; 110008-68-9P; 110008-69-0P; 110008-73-6P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), THU (Therapeutic use), BIOL (Biological study), PREP (Preparation), USES (Uses) (prepn. of, as neoplasm inhibitor); 2998-56-3; 62899-72-3 Role: RCT (Reactant), RACT (Reactant or reagent) (O-carbamoylation by, of (hydroxyphenyl)butene) A1 DE 85-3538734 19851031 | ||||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger | ||||||
| Identification Number: |
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| Keywords: | Neoplasm inhibitors (triphenylbutenes) phenylbutene prepn neoplasm inhibitor butene triphenyl neoplasm inhibitor | ||||||
| Dewey Decimal Classification: | 500 Science > 540 Chemistry & allied sciences | ||||||
| Status: | Published | ||||||
| Refereed: | Yes, this version has been refereed | ||||||
| Created at the University of Regensburg: | Yes | ||||||
| Item ID: | 17662 |
Abstract
The title compds. [I; R1-R3 = H, OR4; R4 = H, (HO)2P(O), alkenoyl, carboxyalkanoyl, (dialkylamino)ethyl, haloacyl, (un)substituted H2NCO; R5 = alkyl] were prepd. as neoplasm inhibitors. PhCH2COCl and PhOMe were refluxed in C2H4Cl2 contg. AlCl3 to give 4-MeOC6H4COCH2Ph. This was refluxed with NaOEt and EtI to give 4-MeOC6H4COCHEtPh. The latter underwent Grignard phenylation with 4-MeOC6H4Br in ...
Abstract
The title compds. [I; R1-R3 = H, OR4; R4 = H, (HO)2P(O), alkenoyl, carboxyalkanoyl, (dialkylamino)ethyl, haloacyl, (un)substituted H2NCO; R5 = alkyl] were prepd. as neoplasm inhibitors. PhCH2COCl and PhOMe were refluxed in C2H4Cl2 contg. AlCl3 to give 4-MeOC6H4COCH2Ph. This was refluxed with NaOEt and EtI to give 4-MeOC6H4COCHEtPh. The latter underwent Grignard phenylation with 4-MeOC6H4Br in Et2O and the product was demethylated with BBr3 and then carbamoylated to give I (R1 = R2 = 4-H2NCO2, R3 = H, R5 = Et) (II). In mice 1.2 mg I/kg s.c. 99% inhibition of growth of MXT-M3.2 mammary tumors . Capsules each contg. 10 mg II were prepd. from II 10, CaHPO4 106.7, gelatin 2.3, polyoxyethylene sorbitan monooleate 1.0, and cornstarch 20 g.
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