PL450925A1 - 2'-Deoxyadenosine derivative in the form of 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine, method for its preparation, and its use as a radiosensitizer - Google Patents

2'-Deoxyadenosine derivative in the form of 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine, method for its preparation, and its use as a radiosensitizer

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Publication number
PL450925A1
PL450925A1 PL450925A PL45092525A PL450925A1 PL 450925 A1 PL450925 A1 PL 450925A1 PL 450925 A PL450925 A PL 450925A PL 45092525 A PL45092525 A PL 45092525A PL 450925 A1 PL450925 A1 PL 450925A1
Authority
PL
Poland
Prior art keywords
deoxyadenosine
trifluorothio
benzylamino
radiosensitizer
formula
Prior art date
Application number
PL450925A
Other languages
Polish (pl)
Inventor
Magdalena Datta
Adrian Szczyrba
Patryk Nowak
Sebastian DEMKOWICZ
Artur Sikorski
Janusz Rak
Original Assignee
Uniwersytet Gdański
Politechnika Gdańska
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Uniwersytet Gdański, Politechnika Gdańska filed Critical Uniwersytet Gdański
Priority to PL450925A priority Critical patent/PL450925A1/en
Publication of PL450925A1 publication Critical patent/PL450925A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
    • 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
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Przedmiotem zgłoszenia jest pochodna 2'-deoksyadenozyny w postaci 8-(4-trifluorotio)benzyloamino-2'-deoksyadenozyny o wzorze 1 oraz jej zastosowanie jako radiosensybilizatora uszkodzeń DNA, która uwrażliwia komórki nowotworowe na promieniowanie jonizujące. Zgłoszenie obejmuje także sposób otrzymywania 8-(4-trifluorotio)benzyloamino-2'-deoksyadenozyny o wzorze 1, który charakteryzuje się tym, że 8-bromo-2'-deoksyadenozynę o wzorze 2 miesza się z 4-trifluorotiobenzyloaminą o wzorze 3 w stosunku molowym 1:8, w obecności metanolu, a następnie mieszaninę ogrzewa się do temperatury wrzenia i miesza przez 72 h.The subject of the application is a 2'-deoxyadenosine derivative in the form of 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine of formula 1 and its use as a radiosensitizer of DNA damage, which sensitizes cancer cells to ionizing radiation. The application also covers a method for obtaining 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine of formula 1, characterized in that 8-bromo-2'-deoxyadenosine of formula 2 is mixed with 4-trifluorothiobenzylamine of formula 3 in a molar ratio of 1:8, in the presence of methanol, and then the mixture is heated to reflux and stirred for 72 h.

PL450925A 2025-01-09 2025-01-09 2'-Deoxyadenosine derivative in the form of 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine, method for its preparation, and its use as a radiosensitizer PL450925A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL450925A PL450925A1 (en) 2025-01-09 2025-01-09 2'-Deoxyadenosine derivative in the form of 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine, method for its preparation, and its use as a radiosensitizer

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL450925A PL450925A1 (en) 2025-01-09 2025-01-09 2'-Deoxyadenosine derivative in the form of 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine, method for its preparation, and its use as a radiosensitizer

Publications (1)

Publication Number Publication Date
PL450925A1 true PL450925A1 (en) 2026-07-13

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PL450925A PL450925A1 (en) 2025-01-09 2025-01-09 2'-Deoxyadenosine derivative in the form of 8-(4-trifluorothio)benzylamino-2'-deoxyadenosine, method for its preparation, and its use as a radiosensitizer

Country Status (1)

Country Link
PL (1) PL450925A1 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130211067A1 (en) * 2010-10-11 2013-08-15 In Seok Hong Novel seleny-methyluracil compounds, radiosensitizer and pharmaceutical composition using them
PL236657B1 (en) * 2018-10-02 2021-02-08 Univ Gdanski Radiosensitizer in the form of 5-iodo-4-thio-2'-deoxyuridine for use in radiotherapy

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130211067A1 (en) * 2010-10-11 2013-08-15 In Seok Hong Novel seleny-methyluracil compounds, radiosensitizer and pharmaceutical composition using them
PL236657B1 (en) * 2018-10-02 2021-02-08 Univ Gdanski Radiosensitizer in the form of 5-iodo-4-thio-2'-deoxyuridine for use in radiotherapy