PL410364A1 - phenyl, alkylophenyl, dialkylophenyl, alkoxyphenyl substituted 3-(4-nitrophenyl)-7,8-dihydroimidazo[2,1-c][1,2,4] triazin-4(6H)-one derivatives, method for obtaining them and medical applications - Google Patents
phenyl, alkylophenyl, dialkylophenyl, alkoxyphenyl substituted 3-(4-nitrophenyl)-7,8-dihydroimidazo[2,1-c][1,2,4] triazin-4(6H)-one derivatives, method for obtaining them and medical applicationsInfo
- Publication number
- PL410364A1 PL410364A1 PL410364A PL41036414A PL410364A1 PL 410364 A1 PL410364 A1 PL 410364A1 PL 410364 A PL410364 A PL 410364A PL 41036414 A PL41036414 A PL 41036414A PL 410364 A1 PL410364 A1 PL 410364A1
- Authority
- PL
- Poland
- Prior art keywords
- phenyl
- cancer
- alkoxyphenyl
- dihydroimidazo
- triazin
- Prior art date
Links
- 125000005036 alkoxyphenyl group Chemical group 0.000 title abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title abstract 3
- LHTLRHMXCMFBLP-UHFFFAOYSA-N 3-(4-nitrophenyl)-7,8-dihydro-6H-imidazo[2,1-c][1,2,4]triazin-4-one Chemical class [N+](=O)([O-])C1=CC=C(C=C1)C=1C(N2C(=NN=1)NCC2)=O LHTLRHMXCMFBLP-UHFFFAOYSA-N 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- -1 dialkylphenyl Chemical group 0.000 abstract 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 abstract 1
- WIPKZLIKOXLWCF-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-ylhydrazine Chemical class NNC1=NCCN1 WIPKZLIKOXLWCF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 206010006187 Breast cancer Diseases 0.000 abstract 1
- 208000026310 Breast neoplasm Diseases 0.000 abstract 1
- 206010008342 Cervix carcinoma Diseases 0.000 abstract 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 206010033128 Ovarian cancer Diseases 0.000 abstract 1
- 206010061535 Ovarian neoplasm Diseases 0.000 abstract 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 201000010881 cervical cancer Diseases 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- ZFCXKZCKJZFZGR-UHFFFAOYSA-N ethyl 2-(4-nitrophenyl)-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CC=C([N+]([O-])=O)C=C1 ZFCXKZCKJZFZGR-UHFFFAOYSA-N 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 201000005202 lung cancer Diseases 0.000 abstract 1
- 208000020816 lung neoplasm Diseases 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 239000003586 protic polar solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem wynalazku są nowe pochodne 3-(4-nitrofenylo)-7,8-dihydroimidazo[2,1-c][1,2,4]triazyn-4(6H)-onu podstawione fenylem, alkilofenylem, dialkilofenylem, alkoksyfenylem o wzorze ogólnym 1, w którym R oznacza podstawnik, taki jak: fenyl, alkilofenyl, zwłaszcza 2-metylofenyl, 4-metylofenyl, dialkilofenyl, zwłaszcza 2,3-dimetylofenyl, lub alkoksyfenyl, zwłaszcza 2-metoksyfenyl, wykazujące działanie przeciwnowotworowe. Związki będące przedmiotem wynalazku otrzymuje się w wyniku kondensacji odpowiednio podstawionych halogenowodorków 2-hydrazynoimidazolin z estrem etylowym kwasu 4-nitrofenyloglioksalowego, stosując stosunek molowy substratów 1 : 1, w środowisku rozpuszczalników organicznych w obecności substancji zasadowych wiążących wydzielający się halogenowodór. Produkt oczyszcza się przez krystalizację z mieszaniny rozpuszczalników polarnych aprotonowych i protonowych zwłaszcza dimetyloformamidu i alkoholu metylowego. Przedmiotem wynalazku jest również medyczne zastosowanie związków o wzorze ogólnym 1 w leczeniu raka, zwłaszcza raka płuc, raka szyjki macicy, raka piersi, a także raka jajnika. The present invention relates to new 3- (4-nitrophenyl) -7,8-dihydroimidazo [2,1-c] [1,2,4] triazin-4 (6H) -one derivatives substituted with phenyl, alkylphenyl, dialkylphenyl, alkoxyphenyl general 1, wherein R is a substituent such as: phenyl, alkylphenyl, especially 2-methylphenyl, 4-methylphenyl, dialkylphenyl, especially 2,3-dimethylphenyl, or alkoxyphenyl, especially 2-methoxyphenyl, having anti-tumor activity. The compounds of the invention are obtained by condensing appropriately substituted 2-hydrazinoimidazoline hydrohalides with 4-nitrophenylglyoxylic acid ethyl ester, using a 1: 1 molar ratio of substrates, in an organic solvent environment in the presence of basic substances that bind hydrogen halide. The product is purified by crystallization from a mixture of polar aprotic and protic solvents, especially dimethylformamide and methyl alcohol. The invention also relates to the medical use of compounds of general formula I in the treatment of cancer, especially lung cancer, cervical cancer, breast cancer and also ovarian cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL410364A PL225419B1 (en) | 2014-12-03 | 2014-12-03 | phenyl, alkylophenyl, dialkylophenyl, alkoxyphenyl substituted 3-(4-nitrophenyl)-7,8-dihydroimidazo[2,1-c][1,2,4] triazin-4(6H)-one derivatives, method for obtaining them and medical applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL410364A PL225419B1 (en) | 2014-12-03 | 2014-12-03 | phenyl, alkylophenyl, dialkylophenyl, alkoxyphenyl substituted 3-(4-nitrophenyl)-7,8-dihydroimidazo[2,1-c][1,2,4] triazin-4(6H)-one derivatives, method for obtaining them and medical applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL410364A1 true PL410364A1 (en) | 2015-09-14 |
| PL225419B1 PL225419B1 (en) | 2017-04-28 |
Family
ID=54065033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL410364A PL225419B1 (en) | 2014-12-03 | 2014-12-03 | phenyl, alkylophenyl, dialkylophenyl, alkoxyphenyl substituted 3-(4-nitrophenyl)-7,8-dihydroimidazo[2,1-c][1,2,4] triazin-4(6H)-one derivatives, method for obtaining them and medical applications |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL225419B1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL447851A1 (en) * | 2024-02-26 | 2025-09-01 | Uniwersytet Medyczny W Lublinie | 8-Substituted-3-(4-chlorophenyl)-7,8-dihydroimidazo[2,1-c][1,2,4]triazin-4(6H)-ones, method of their preparation and medical use |
-
2014
- 2014-12-03 PL PL410364A patent/PL225419B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL225419B1 (en) | 2017-04-28 |
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