MD4179C1 - Compuşi coordinativi ai cuprului(II), care conţin 4-feniltiosemicarbazona 2-formilpiridinei şi sulfanilamide, care manifestă activitate antimicrobiană faţă de bacteriile din specia Bacillus cereus - Google Patents
Compuşi coordinativi ai cuprului(II), care conţin 4-feniltiosemicarbazona 2-formilpiridinei şi sulfanilamide, care manifestă activitate antimicrobiană faţă de bacteriile din specia Bacillus cereus Download PDFInfo
- Publication number
- MD4179C1 MD4179C1 MDA20110051A MD20110051A MD4179C1 MD 4179 C1 MD4179 C1 MD 4179C1 MD A20110051 A MDA20110051 A MD A20110051A MD 20110051 A MD20110051 A MD 20110051A MD 4179 C1 MD4179 C1 MD 4179C1
- Authority
- MD
- Moldova
- Prior art keywords
- copper
- compounds
- formylpyridine
- phenylthiosemicarbazone
- xii
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 15
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 241000193755 Bacillus cereus Species 0.000 title claims abstract description 13
- 241000894006 Bacteria Species 0.000 title claims abstract description 9
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 title claims abstract description 7
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 title 1
- 230000001747 exhibiting effect Effects 0.000 title 1
- 239000003814 drug Substances 0.000 abstract description 7
- 229940124530 sulfonamide Drugs 0.000 abstract description 3
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 239000010949 copper Substances 0.000 description 14
- 229910052802 copper Inorganic materials 0.000 description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 244000005700 microbiome Species 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 8
- SVYBEBLNQGDRHF-UHFFFAOYSA-N 4-amino-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide Chemical compound S1C(CC)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 SVYBEBLNQGDRHF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 6
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 6
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 6
- 229910002651 NO3 Inorganic materials 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 5
- 229960001544 sulfathiazole Drugs 0.000 description 5
- 229940034107 sulfazine Drugs 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 150000004699 copper complex Chemical class 0.000 description 4
- -1 copper(2+) ion Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical group CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- GXBCCUBTQFNGFA-BJMVGYQFSA-N [(e)-pyridin-2-ylmethylideneamino]thiourea Chemical compound NC(=S)N\N=C\C1=CC=CC=N1 GXBCCUBTQFNGFA-BJMVGYQFSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- JHWPKWSWTSDZLG-UHFFFAOYSA-N 1-phenyl-3-(pyridin-2-ylmethylideneamino)thiourea Chemical compound C=1C=CC=CC=1NC(=S)NN=CC1=CC=CC=N1 JHWPKWSWTSDZLG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001148132 Salmonella enterica subsp. enterica serovar Abony Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- ZAMOJKJKCBOKFV-UHFFFAOYSA-N aniline;sulfamide Chemical compound NS(N)(=O)=O.NC1=CC=CC=C1 ZAMOJKJKCBOKFV-UHFFFAOYSA-N 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ABBQGOCHXSPKHJ-WUKNDPDISA-N prontosil Chemical compound NC1=CC(N)=CC=C1\N=N\C1=CC=C(S(N)(=O)=O)C=C1 ABBQGOCHXSPKHJ-WUKNDPDISA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229960002673 sulfacetamide Drugs 0.000 description 2
- 229950008188 sulfamidochrysoidine Drugs 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003584 thiosemicarbazones Chemical class 0.000 description 2
- GXBCCUBTQFNGFA-UHFFFAOYSA-N (pyridin-2-ylmethylideneamino)thiourea Chemical compound NC(=S)NN=CC1=CC=CC=N1 GXBCCUBTQFNGFA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001360526 Escherichia coli ATCC 25922 Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 229940127395 Ribonucleotide Reductase Inhibitors Drugs 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- JZLUWZPEJDRDEO-UHFFFAOYSA-N [N].C1=CN=CN=C1 Chemical group [N].C1=CN=CN=C1 JZLUWZPEJDRDEO-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005837 enolization reaction Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical class O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229960003288 sulfaethidole Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20110051A MD4179C1 (ro) | 2011-05-23 | 2011-05-23 | Compuşi coordinativi ai cuprului(II), care conţin 4-feniltiosemicarbazona 2-formilpiridinei şi sulfanilamide, care manifestă activitate antimicrobiană faţă de bacteriile din specia Bacillus cereus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20110051A MD4179C1 (ro) | 2011-05-23 | 2011-05-23 | Compuşi coordinativi ai cuprului(II), care conţin 4-feniltiosemicarbazona 2-formilpiridinei şi sulfanilamide, care manifestă activitate antimicrobiană faţă de bacteriile din specia Bacillus cereus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4179B1 MD4179B1 (en) | 2012-07-31 |
| MD4179C1 true MD4179C1 (ro) | 2013-02-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20110051A MD4179C1 (ro) | 2011-05-23 | 2011-05-23 | Compuşi coordinativi ai cuprului(II), care conţin 4-feniltiosemicarbazona 2-formilpiridinei şi sulfanilamide, care manifestă activitate antimicrobiană faţă de bacteriile din specia Bacillus cereus |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4179C1 (mo) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985000955A1 (en) * | 1983-08-22 | 1985-03-14 | A/S Cheminova | A biocidal, particularly fungicidal and/or bactericidal composition and thiosemicarbazones and metal complexes thereof for use in the composition |
| MD3032F1 (ro) * | 2005-10-31 | 2006-04-30 | Universitatea De Stat Din Moldova | Naftalidentiosemicarbazidati de cupru(II) care contin sulfanilamide |
| MD3124B1 (ro) * | 2005-05-25 | 2006-08-31 | Universitatea De Stat De Medicina Si Farmacie "Nicolae Testemitanu" Din Republica Moldova | Salicilidentiosemicarbazidati de cupru(II)care contin sulfanilamide |
-
2011
- 2011-05-23 MD MDA20110051A patent/MD4179C1/ro not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985000955A1 (en) * | 1983-08-22 | 1985-03-14 | A/S Cheminova | A biocidal, particularly fungicidal and/or bactericidal composition and thiosemicarbazones and metal complexes thereof for use in the composition |
| MD3124B1 (ro) * | 2005-05-25 | 2006-08-31 | Universitatea De Stat De Medicina Si Farmacie "Nicolae Testemitanu" Din Republica Moldova | Salicilidentiosemicarbazidati de cupru(II)care contin sulfanilamide |
| MD3032F1 (ro) * | 2005-10-31 | 2006-04-30 | Universitatea De Stat Din Moldova | Naftalidentiosemicarbazidati de cupru(II) care contin sulfanilamide |
Non-Patent Citations (1)
| Title |
|---|
| Ello H. Antimicrobial activity of two antitumour agents and ribonucleotide reductase inhibitors, pyridine-2-carboxaldehyde thiosemicarbazone and the acetate form of its copper(II) chelate. Z. Naturforsch, 2007, Jul-Aug, 67(7-8), p. 498-506 (regăsit în Internet la 2012.03.01 url: <http://www.ncbi.nlm.nih.gov/pubmed/17913063>) * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4179B1 (en) | 2012-07-31 |
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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 |