MD4402C1 - Метил-N'-[(2-гидроксинафтален-1-ил)метилиден]-N-проп-2-ен-1-илгидразонотиоат, проявляющий противогрибковую активность в отношении Candida albicans - Google Patents
Метил-N'-[(2-гидроксинафтален-1-ил)метилиден]-N-проп-2-ен-1-илгидразонотиоат, проявляющий противогрибковую активность в отношении Candida albicans Download PDFInfo
- Publication number
- MD4402C1 MD4402C1 MDA20150084A MD20150084A MD4402C1 MD 4402 C1 MD4402 C1 MD 4402C1 MD A20150084 A MDA20150084 A MD A20150084A MD 20150084 A MD20150084 A MD 20150084A MD 4402 C1 MD4402 C1 MD 4402C1
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- MD
- Moldova
- Prior art keywords
- candida albicans
- ylhydrazonothioate
- activity against
- methylidene
- prop
- Prior art date
Links
- 241000222122 Candida albicans Species 0.000 title claims abstract description 12
- 229940095731 candida albicans Drugs 0.000 title claims abstract description 12
- 230000000843 anti-fungal effect Effects 0.000 title claims abstract description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 title claims description 7
- 230000001747 exhibiting effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- -1 2-hydroxynaphthalen-1-yl Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 abstract description 8
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 150000003584 thiosemicarbazones Chemical class 0.000 abstract description 3
- 238000011282 treatment Methods 0.000 abstract description 3
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 206010017533 Fungal infection Diseases 0.000 abstract 1
- 208000024386 fungal infectious disease Diseases 0.000 abstract 1
- 241000233866 Fungi Species 0.000 description 6
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000001857 anti-mycotic effect Effects 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CZLPCLANGIXFIE-UHFFFAOYSA-N 1-amino-3-prop-2-enylthiourea Chemical compound NNC(=S)NCC=C CZLPCLANGIXFIE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 125000000746 allylic group Chemical group 0.000 description 2
- 239000002543 antimycotic Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 208000027534 Emotional disease Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 102000007537 Type II DNA Topoisomerases Human genes 0.000 description 1
- 108010046308 Type II DNA Topoisomerases Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 208000002399 aphthous stomatitis Diseases 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229960000988 nystatin Drugs 0.000 description 1
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N thiosemicarbazide group Chemical group NNC(=S)N BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Изобретение относится к химии и медицине, а именно к биологически активному органическому соединению класса тиосемикарбазонов.Сущность изобретения заключается в синтезе соединения метил-N'-[(2-гидроксинафтален-1-ил)метилиден]-N-проп-2-ен-1-илгидразонотиоат формулы:Соединение проявляет противогрибковую активность в отношении Candida albicans и может найти применение в медицине и ветеринарии для профилактики и лечения микозов.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20150084A MD4402C1 (ru) | 2015-09-04 | 2015-09-04 | Метил-N'-[(2-гидроксинафтален-1-ил)метилиден]-N-проп-2-ен-1-илгидразонотиоат, проявляющий противогрибковую активность в отношении Candida albicans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20150084A MD4402C1 (ru) | 2015-09-04 | 2015-09-04 | Метил-N'-[(2-гидроксинафтален-1-ил)метилиден]-N-проп-2-ен-1-илгидразонотиоат, проявляющий противогрибковую активность в отношении Candida albicans |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4402B1 MD4402B1 (ru) | 2016-02-29 |
| MD4402C1 true MD4402C1 (ru) | 2016-09-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20150084A MD4402C1 (ru) | 2015-09-04 | 2015-09-04 | Метил-N'-[(2-гидроксинафтален-1-ил)метилиден]-N-проп-2-ен-1-илгидразонотиоат, проявляющий противогрибковую активность в отношении Candida albicans |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4402C1 (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4452C1 (ru) * | 2016-02-29 | 2017-07-31 | Государственный Университет Молд0 | Применение N-(2,4-диметилфенил)-2-(2-гидроксибензилиден)-гидразинкарботиоамида в качестве ингибитора роста и размножения грибов вида Candida albicans |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD1812B1 (en) * | 2000-12-29 | 2001-12-31 | Univ Nicolae Testemitanu | Copper complexes as bacteria and fungi inhibitors |
| MD2003B1 (en) * | 2001-01-10 | 2002-09-30 | Univ Nicolae Testemitanu | Copper chelate compounds(II) with antimicrobial and antimycotic activity |
| MD4194B1 (en) * | 2012-01-23 | 2013-01-31 | Univ De Stat Din Moldova | Trinuclear coordinative compound tris{µ-¢3,5-dibromo-2-hydroxybenzylidene-4′-(pyridin-2-yl)-thiosemicarbazido(2-)]copper}hydrate, exhibiting antifungal activity against Candida albicans |
| MD4258B1 (en) * | 2012-05-31 | 2013-11-30 | Univ De Stat Din Moldova | The use of biologically active coordinative compounds of copper(II) with 4-(methoxyphenyl)thiosemicarbazones of 2-benzoylpyridine as inhibitors of Candida albicans |
-
2015
- 2015-09-04 MD MDA20150084A patent/MD4402C1/ru not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD1812B1 (en) * | 2000-12-29 | 2001-12-31 | Univ Nicolae Testemitanu | Copper complexes as bacteria and fungi inhibitors |
| MD2003B1 (en) * | 2001-01-10 | 2002-09-30 | Univ Nicolae Testemitanu | Copper chelate compounds(II) with antimicrobial and antimycotic activity |
| MD4194B1 (en) * | 2012-01-23 | 2013-01-31 | Univ De Stat Din Moldova | Trinuclear coordinative compound tris{µ-¢3,5-dibromo-2-hydroxybenzylidene-4′-(pyridin-2-yl)-thiosemicarbazido(2-)]copper}hydrate, exhibiting antifungal activity against Candida albicans |
| MD4258B1 (en) * | 2012-05-31 | 2013-11-30 | Univ De Stat Din Moldova | The use of biologically active coordinative compounds of copper(II) with 4-(methoxyphenyl)thiosemicarbazones of 2-benzoylpyridine as inhibitors of Candida albicans |
Non-Patent Citations (3)
| Title |
|---|
| He Huang, Qin Chen, Xin Ku, Linghua Meng, Liping Lin, Xiang Wang, Caihua Zhu, Yi Wang, Zhi Chen, Ming Li, Hualiang Jiang, Kaixian Chen, Jian Ding, Hong Liu. A Series of a-Heterocyclic Carboxaldehyde Thiosemicarbazones Inhibit Topoisomerase IIa Catalytic Activity. Journal of Medicinal Chemistry, 2010, vol. 53, p. 3048-3064 * |
| Liberta A., West D. Antifungal and antitumor activity of heterocyclic thiosemicarbazones and their metal complexes: current status. BioMetals, 1992, p. 121-126 (regăsit în Internet la 2015.11.23 URL:<http://www.ncbi.nlm.nih.gov/pubmed/1525478>) * |
| Pahontu E., Julea F., Rosu T., Purcarea V., Chumakov Yu., Petrenco P., Gulea A. Antibacterial, antifungal and in vitro antileukaemia activity of metal complexes with thiosemicarbazones. Journal of Cellular and Molecular Medicine, 2015 April, p. 865-878 (regăsit în Internet la 2015.12.01 URL:<http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4395200/>) * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4402B1 (ru) | 2016-02-29 |
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| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |