PL448581A1 - 2-(4-Hydroxy-3-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application - Google Patents
2-(4-Hydroxy-3-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical applicationInfo
- Publication number
- PL448581A1 PL448581A1 PL448581A PL44858124A PL448581A1 PL 448581 A1 PL448581 A1 PL 448581A1 PL 448581 A PL448581 A PL 448581A PL 44858124 A PL44858124 A PL 44858124A PL 448581 A1 PL448581 A1 PL 448581A1
- Authority
- PL
- Poland
- Prior art keywords
- reaction
- hydrazinecarbothioamide
- hydroxy
- naphth
- nitrobenzoyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem zgłoszenia jest nowa pochodna hydrazynokarbotioamidu, o wzorze ogólnym 1 przedstawionym na rysunku, będąca jednoczesnym inhibitorem ludzkiej topoizomerazy II oraz tyrozynazy do zastosowania w leczeniu czerniaka. Zgłoszenie obejmuje także sposób wytwarzania nowej pochodnej hydrazynokarbotioamidu o wzorze ogólnym 1, charakteryzujący się tym, że hydrazyd kwasu 4-hydroksy-3-nitrobenzoesowego poddaje się reakcji z izotiocyjanianem 1-naftylometylu, prowadząc reakcję w rozpuszczalnikach organicznych, gdzie postęp reakcji kontroluje się przy użyciu technik chromatograficznych, a po zakończeniu reakcji mieszaninę reakcyjną ochładza się, powstały osad odsącza, suszy, a następnie krystalizuje z rozpuszczalników polarnych. Reakcję w rozpuszczalnikach organicznych prowadzi się we wrzącym etanolu, korzystnie w czasie przez 5 — 30 minut, zaś otrzymany produkt reakcji krystalizuje się z etanolu.The subject of the application is a new hydrazinecarbothioamide derivative, of general formula 1 shown in the drawing, being a simultaneous inhibitor of human topoisomerase II and tyrosinase for use in the treatment of melanoma. The application also covers a method of producing a new hydrazinecarbothioamide derivative of general formula 1, characterized in that 4-hydroxy-3-nitrobenzoic acid hydrazide is reacted with 1-naphthylmethyl isothiocyanate, carrying out the reaction in organic solvents, where the progress of the reaction is controlled using chromatographic techniques, and after the reaction is completed, the reaction mixture is cooled, the resulting precipitate is filtered off, dried, and then crystallized from polar solvents. The reaction in organic solvents is carried out in boiling ethanol, preferably for 5-30 minutes, and the obtained reaction product is crystallized from ethanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL448581A PL247927B1 (en) | 2024-05-15 | 2024-05-15 | 2-(4-Hydroxy-3-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL448581A PL247927B1 (en) | 2024-05-15 | 2024-05-15 | 2-(4-Hydroxy-3-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL448581A1 true PL448581A1 (en) | 2024-12-02 |
| PL247927B1 PL247927B1 (en) | 2025-09-15 |
Family
ID=93706957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL448581A PL247927B1 (en) | 2024-05-15 | 2024-05-15 | 2-(4-Hydroxy-3-nitrobenzoyl)-N-[(naphth-1-yl)methyl]hydrazinecarbothioamide, method of its production and its first medical application |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL247927B1 (en) |
-
2024
- 2024-05-15 PL PL448581A patent/PL247927B1/en unknown
Non-Patent Citations (3)
| Title |
|---|
| GOOGLE; A. Szopa et al., Evaluation of developmental toxicity in zebrafish embryos and antiproliferative potential against human tumor cell lines of new derivatives containing 4-nitrophenyl group. Toxicol Appl Pharmacol. 2023 Jan; 458: 116325 * |
| GOOGLE; Kozyra et al., Potential Anticancer Agents against Melanoma Cells Based on an As-Synthesized Thiosemicarbazide Derivative. Biomolecules. 2022; 12(2):151 * |
| GOOGLE; M. Wos et al., Novel thiosemicarbazide derivatives with 4-nitrophenyl group as multi-target drugs: α-glucosidase inhibitors with antibacterial and antiproliferative activity. Biomed Pharmacother. 2017; 93: 1269-1276 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL247927B1 (en) | 2025-09-15 |
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