PL422341A1 - Alpha thiosemicarbazone dialkyl ketophosphonates and method for producing them - Google Patents
Alpha thiosemicarbazone dialkyl ketophosphonates and method for producing themInfo
- Publication number
- PL422341A1 PL422341A1 PL422341A PL42234117A PL422341A1 PL 422341 A1 PL422341 A1 PL 422341A1 PL 422341 A PL422341 A PL 422341A PL 42234117 A PL42234117 A PL 42234117A PL 422341 A1 PL422341 A1 PL 422341A1
- Authority
- PL
- Poland
- Prior art keywords
- dialkyl
- ketophosphonates
- thiosemicarbazones
- alkyl group
- ketophosphonate
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 title 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 abstract 4
- 150000003584 thiosemicarbazones Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000003377 acid catalyst Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 238000011319 anticancer therapy Methods 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Przedmiotem zgłoszenia są tiosemikarbazony α-ketofosfonianów dialkilowych o wzorze 1, w którym R oznacza podstawnik arylowy, w tym naftyl podstawiony w pozycji 1- lub 2-, fenyl, ewentualnie podstawiony innymi grupami funkcyjnymi takimi jak grupa alkilowa, grupa arylowa, grupa alkoksylowa, grupa alkilosulfanylowa, dialkiloaminowa i atomy chlorowca, lub grupę alkilową od C1 do C13, natomiast Alk oznacza grupę alkilową od C1 do C6, w tym metyl, etyl, butyl, izopropyl lub heksyl, znajdujące zastosowanie w terapii przeciwnowotworowej. Zgłoszenie dotyczy również sposobu wytwarzania tiosemikarbazonów α-ketofosfonianów dialkilowych, który polega na tym, że jedną część molową α-ketofosfonianu dialkilowego poddaje się reakcji z co najmniej jedną częścią molową tiosemikarbazydu wobec kwaśnego katalizatora, przy czym reakcję prowadzi się w temperaturze 273 - 373K w alkoholu, aż do przereagowania substratów. W innym wariancie sposobu wytwarzania tiosemikarbazonów α-ketofosfonianów dialkilowych reakcji z tiosemikarbazydem wobec kwaśnego katalizatora poddaje się surowe α-ketofosfoniany dialkilowe, wytworzone w reakcji odpowiedniego halogenku kwasowego z fosforynem trójalkilowym w rozpuszczalniku organicznym. Tytułowe tiosemikarbazony α-ketofosfonianów dialkilowych otrzymuje się w formie izomeru E lub Z, lub mieszaniny izomerów E i Z.The subject of the application are thiosemicarbazones of dialkyl α-ketophosphonates of formula 1, in which R is an aryl substituent, including naphthyl substituted in the 1- or 2-position, phenyl, optionally substituted with other functional groups such as an alkyl group, aryl group, alkoxy group, alkylsulfanyl, dialkylamino and halogen atoms, or an alkyl group from C1 to C13, while Alk means an alkyl group from C1 to C6, including methyl, ethyl, butyl, isopropyl or hexyl, used in anticancer therapy. The application also concerns a method for preparing dialkyl α-ketophosphonate thiosemicarbazones, which consists in reacting one mole of dialkyl α-ketophosphonate with at least one mole of thiosemicarbazide in the presence of an acid catalyst, and the reaction is carried out at a temperature of 273 - 373K in alcohol. until the substrates are reacted. In another variant of the process for preparing dialkyl α-ketophosphonates thiosemicarbazones, crude dialkyl α-ketophosphonates prepared by reacting the appropriate acid halide with trialkyl phosphite in an organic solvent are reacted with thiosemicarbazide in the presence of an acid catalyst. The title thiosemicarbazones of dialkyl α-ketophosphonates are obtained in the form of the E or Z isomer, or a mixture of E and Z isomers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422341A PL244594B1 (en) | 2017-07-25 | 2017-07-25 | Alpha thiosemicarbazone dialkyl ketophosphonates and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422341A PL244594B1 (en) | 2017-07-25 | 2017-07-25 | Alpha thiosemicarbazone dialkyl ketophosphonates and method for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL422341A1 true PL422341A1 (en) | 2018-03-26 |
| PL244594B1 PL244594B1 (en) | 2024-02-12 |
Family
ID=61661194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL422341A PL244594B1 (en) | 2017-07-25 | 2017-07-25 | Alpha thiosemicarbazone dialkyl ketophosphonates and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL244594B1 (en) |
-
2017
- 2017-07-25 PL PL422341A patent/PL244594B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL244594B1 (en) | 2024-02-12 |
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