CN105524082A - Synthesis and antibacterial activity of zinc voriconazole complex - Google Patents
Synthesis and antibacterial activity of zinc voriconazole complex Download PDFInfo
- Publication number
- CN105524082A CN105524082A CN201510870750.9A CN201510870750A CN105524082A CN 105524082 A CN105524082 A CN 105524082A CN 201510870750 A CN201510870750 A CN 201510870750A CN 105524082 A CN105524082 A CN 105524082A
- Authority
- CN
- China
- Prior art keywords
- synthesis
- title complex
- purposes
- complex
- voriconazole
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 title claims abstract description 12
- 229960004740 voriconazole Drugs 0.000 title claims abstract description 12
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 6
- 230000015572 biosynthetic process Effects 0.000 title claims description 20
- 238000003786 synthesis reaction Methods 0.000 title claims description 20
- 239000011701 zinc Substances 0.000 title claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims 2
- 229910052725 zinc Inorganic materials 0.000 title claims 2
- 201000007336 Cryptococcosis Diseases 0.000 claims abstract description 3
- 241000221204 Cryptococcus neoformans Species 0.000 claims abstract description 3
- 241001225321 Aspergillus fumigatus Species 0.000 claims abstract 2
- 241000228245 Aspergillus niger Species 0.000 claims abstract 2
- 241000222126 [Candida] glabrata Species 0.000 claims abstract 2
- 208000032343 candida glabrata infection Diseases 0.000 claims abstract 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 12
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- 238000011160 research Methods 0.000 claims description 6
- -1 tetracol phenixin Chemical compound 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 241000370738 Chlorion Species 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 229940091771 aspergillus fumigatus Drugs 0.000 claims 1
- 230000004071 biological effect Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- 229940006461 iodide ion Drugs 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000012046 mixed solvent Substances 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 abstract description 4
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 241000228197 Aspergillus flavus Species 0.000 abstract 1
- 241001465318 Aspergillus terreus Species 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000005284 excitation Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 4
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 3
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 2
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 2
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RHMXXJGYXNZAPX-UHFFFAOYSA-N emodin Chemical compound C1=C(O)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O RHMXXJGYXNZAPX-UHFFFAOYSA-N 0.000 description 2
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 2
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 2
- 229960004884 fluconazole Drugs 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 description 1
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 description 1
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 description 1
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 description 1
- 241000228404 Histoplasma capsulatum Species 0.000 description 1
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 description 1
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012822 chemical development Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 description 1
- 229940058690 lanosterol Drugs 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000010197 meta-analysis Methods 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a synthetic method for a complex containing voriconazole. Ultraviolet, infrared, fluorescent and antibacterial activities of the complex are further researched by determining the crystal structure of the complex via monocrystalline X-rays. Ultraviolet absorption occurs when wavelengths are 207 nm (wherein Abs is equal to 0.48) and 256 nm (wherein Abs is equal to 0.40). When excitation wavelength is 220 nm, emission wavelength is 377 nm. Testing results show that the complex has strong antibacterial activity to Candida glabrata, Cryptococcus neoformans, Aspergillus niger, Aspergillus terreus, Aspergillus fumigates, Aspergillus flavus and the like and is expected to become a novel antibacterial agent.
Description
Technical field
The invention belongs to inorganic chemistry, organic chemistry and medicinal chemistry art, relate to the synthesis of metal complexes and the research of structure, fluorescence and anti-microbial activity.
Background technology
Metal complexes has novel structure and unique character, such as in antibacterial, catalysis, gas adsorption, atmosphere storage, fluorescence, sensing and medicament transport, there is potential using value (G.V.Kurlyandskaya, V.A.Lukshina, A.Larra aga, I.Orue, A.A.Zaharova, D.A.Shishkin, J.AlloysCompd., 2013,566,31-36; X.M.Zhang, R.Q.Fang, Inorg.Chem., 2005,44,3955-3959; Q.L.Li, J.P.Wang, W.C.Liu, X.Y.Zhuang, J.Q.Liu, G.L.Fan, B.H.Li, W.N.Lin, J.H.Man, Inorg.Chem.Commun., 2015,55,8-10; J.L.Harding, J.M.Metz, M.M.Reynolds, Adv.Funct.Mater., 2014,24,7503-7509).For the synthesis of metal complexes, conventional method has conventional soln reaction method, hydrothermal method and solvent-thermal method etc., therefore synthesizes the title complex with special construction and character and still has certain difficulty.
Voriconazole is a kind of New-type wide-spectrum antifungal drug in triazole class, can the demethylation of 14 α-sterol of Antifungi cytochrome P 450 mediated, thus the synthesis of Antifungi ergosterol, to the selectivity of fungal cytochrome P450 enzyme higher than various mammiferous cytochrome P 450 Enzyme.Voriconazole suppresses yeast also to kill some thread organism, compares saccharomycetic higher the affinity of the lanosterol 14 α-demethyl enzyme of mould, ergosterol can be made to synthesize and be obstructed completely, cause necrocytosis.It has fabulous anti-microbial activity to the Candida albicans of resistance to fluconazole, to the saccharomycetic anti-microbial activity of pathogenicity bo higher than fluconazole, to the mould Pseudomonas of sufficient branch, Fusarium, Histoplasma capsulatum, the raw bacterium of dermatitis tooth and cryptococcus neoformans also have activity (Li Fangfang. the meta-analysis of voriconazole prevention invasive infections with fungi effectiveness and reliability. China infects and chemotherapy magazine, 2012,12, (6): 453-458).
In recent years, the title complex formed by medicine organic molecule achieve in medical research certain progress (Zhu is dragon early. the research of the synthesis of the large ring schiff bases complex of rare earth curcumine, sign and bacteriostatic activity thereof: [D]. Lanzhou: Northwest Normal University's chemistry and chemical engineering institute, 2009; Bao Juan. the synthesis of benzimidazoles compound and title complex thereof and activity research: [D]. Guangzhou: medicine academy of sciences of Guangdong Pharmaceutical University, 2009).Schuttgelb reacts form Schuttgelb metal complexes with Cu (II), Co (II), Ni (II), Zn (II), Mn (II) transition metal ion respectively, these metal complexess have obvious anti-tumor activity (poplar Lee. the synthesis of Schuttgelb transition metal complex and antitumor activity: [D]. Chongqing: biological engineering college of University Of Chongqing, 2014).By own azoles alcohol and bivalent cupric ion react the title complex obtained have effective bacteriostatic activity (Bi Yanbo. own azoles alcohol copper complex bacteriostatic activity and plant growth regulating effect research: [D]. Xi'an: Northwest University, 2012).
Therefore synthesis contains the title complex of voriconazole and studies its character, not only plays huge pushing effect to coordination chemistry but also to organic chemistry and pharmaceutical chemical development.
Summary of the invention
The invention provides a kind of synthetic method of synthetic compound, and its spectral quality, anti-microbial activity are studied.
Concrete synthesis step of the present invention.
The synthesis of embodiment one, compound
By voriconazole 0.035g(0.1mmol) and 0.014g(0.1mmol) the water-soluble and methyl alcohol of zinc chloride mixed solution in, then transferred in flask by reaction solution and heat, temperature of reaction is 65 degree.Reaction solution is down to room temperature after reacting 10 minutes, moves in test tube.White plates crystal 1 is obtained after 5 days.Products obtained therefrom 1 is determined its molecular structure through Advances in crystal X-ray diffraction analysis, sees Fig. 1.
The germ resistance of product 1 is tested, its anti-microbial activity (MIC-
50, μ gmL
-1) as table one, two.
The anti-microbial activity of table one different population
The antibacterial work of table two mould series is studied carefully
Accompanying drawing explanation
The crystalline structure figure of Fig. 1, compound 1.
The ultraviolet spectrogram of Fig. 2, compound 1.
The infrared spectrogram of Fig. 3, compound 1.
The fluorescence spectrum figure of Fig. 4, compound 1.
Embodiment
Be described in detail embodiments of the invention below, the present embodiment is implemented under premised on technical solution of the present invention, give detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
The invention provides a kind of synthetic method of title complex, and its ultraviolet, infrared, the character such as fluorescence and anti-microbial activity are studied.
For achieving the above object, by voriconazole and the water-soluble and methyl alcohol of zinc chloride, then transferred in flask by reaction solution and heat, temperature of reaction is 65 degree.Reaction solution is down to room temperature after reacting 10 minutes, is moved in test tube by reaction solution.White plates crystal 1 is obtained after 5 days.Products obtained therefrom 1 is determined its molecular structure through Advances in crystal X-ray diffraction analysis, sees Fig. 1.
Concrete synthesis step of the present invention is as follows.
The synthesis of embodiment one, product 1
By voriconazole 0.035g(0.1mmol) and 0.014g(0.1mmol) the water-soluble and methyl alcohol of zinc chloride mixed solution in, then reaction solution is transferred in flask and is heated, and temperature of reaction is 65 degree.Reaction solution is down to room temperature after reacting 10 minutes, and moves in test tube.White plates crystal 1 is obtained after 5 days.Products obtained therefrom 1 is determined its molecular structure through Advances in crystal X-ray diffraction analysis, sees Fig. 1.
Claims (6)
1. the synthesis of voriconazole Zn complex and the research of anti-microbial activity thereof, this title complex can be used for antibacterials, it is characterized in that:
(1) synthesis of embodiment one, title complex 1
A certain proportion of voriconazole and zinc chloride are dissolved in a certain amount of water and organic solvent; Then transfer in flask by reaction mixture, after having heated, be down to room temperature, filter, leave standstill, separate out the target product 1 of white and determine its crystalline structure;
(2) biological activity of embodiment two, metallic zinc title complex
Its anti-microbial activity measuring process: get after appropriate product 1 is dissolved in suitable solvent for some time at moderate temperatures, measure its anti-microbial activity.
2. the synthesis of the title complex according to claims 1 and purposes, is characterized in that selected temperature range is from room temperature to 100 degrees Celsius.
3. the synthesis of the title complex according to claims 1 and purposes, is characterized in that heat-up time was from 5 minutes to 30 minutes.
4. the synthesis of the title complex according to claims 1 and purposes, it is characterized in that selected organic solvent to be carbon atom quantity be single solvent or the mixed solvent of the unit alcohol of 1-10, acetone, ethyl acetate, dimethyl sulfoxide (DMSO), DMF, methylene dichloride, trichloromethane, tetracol phenixin, Nitromethane 99Min., tetrahydrofuran (THF), N-Methyl pyrrolidone, sherwood oil, benzene, toluene.
5. the synthesis of the title complex according to claims 1 and purposes, is characterized in that in selected zinc salt, negatively charged ion is fluorion, chlorion, bromide anion, iodide ion, sulfate radical, formate, acetate, tetrafluoroborate.
6. the synthesis of the title complex according to claims 1 and purposes, is characterized in that such title complex has very strong anti-microbial activity to Candida glabrata, Cryptococcus neoformans, aspergillus niger, terreus, Aspergillus fumigatus, flavus etc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510870750.9A CN105524082A (en) | 2015-12-01 | 2015-12-01 | Synthesis and antibacterial activity of zinc voriconazole complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510870750.9A CN105524082A (en) | 2015-12-01 | 2015-12-01 | Synthesis and antibacterial activity of zinc voriconazole complex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105524082A true CN105524082A (en) | 2016-04-27 |
Family
ID=55766644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510870750.9A Pending CN105524082A (en) | 2015-12-01 | 2015-12-01 | Synthesis and antibacterial activity of zinc voriconazole complex |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105524082A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103923110A (en) * | 2014-04-03 | 2014-07-16 | 哈尔滨工业大学 | Benzimidazole derivative metal complex with antibacterial activity and preparation method of complex |
| CN104399086A (en) * | 2014-12-05 | 2015-03-11 | 重庆市畜牧科学院 | Clathrate compound of aureomycin zinc complex, and preparation method thereof |
-
2015
- 2015-12-01 CN CN201510870750.9A patent/CN105524082A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103923110A (en) * | 2014-04-03 | 2014-07-16 | 哈尔滨工业大学 | Benzimidazole derivative metal complex with antibacterial activity and preparation method of complex |
| CN104399086A (en) * | 2014-12-05 | 2015-03-11 | 重庆市畜牧科学院 | Clathrate compound of aureomycin zinc complex, and preparation method thereof |
Non-Patent Citations (4)
| Title |
|---|
| ADAM Z. ET AL: ""Activity of fluconazole and its Cu(II) complex towards Candida species"", 《MED CHEM RES》 * |
| 傅文红等: ""配合物{[Co(HFlu)2Cl2]•2C2H5OH}n的合成、结构及体外抗真菌活性"", 《广东化工》 * |
| 张培志等: ""三唑酮氯化锌配合物的合成和晶体结构研究"", 《无机化学学报》 * |
| 王艳等: ""三唑类药物研究新进展"", 《中国科学: 化学》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Saif et al. | Synthesis, characterization, and antioxidant/cytotoxic activity of new chromone Schiff base nano-complexes of Zn (II), Cu (II), Ni (II) and Co (II) | |
| Rehman et al. | Synthesis, characterization, antimicrobial and antitumor screening of some diorganotin (IV) complexes of 2-[(9H-Purin-6-ylimino)]-phenol | |
| Shreaz et al. | Anticandidal activity of cinnamaldehyde, its ligand and Ni (II) complex: effect of increase in ring and side chain | |
| Achar et al. | Sterically modulated silver (I) complexes of coumarin substituted benzimidazol–2–ylidenes: Synthesis, crystal structures and evaluation of their antimicrobial and antilung cancer potentials | |
| Alomar et al. | Synthesis, crystal structure, characterisation, and antifungal activity of 3-thiophene aldehyde semicarbazone (3STCH), 2, 3-thiophene dicarboxaldehyde bis (semicarbazone)(2, 3BSTCH2) and their nickel (II) complexes | |
| Aghatabay et al. | Raman, FT-IR, NMR spectroscopic data and antimicrobial activity of bis [μ2-(benzimidazol-2-yl)-2-ethanethiolato-N, S, S-chloro-palladium (II)] dimer,[(μ2-CH2CH2NHNCC6H4) PdCl] 2· C2H5OH complex | |
| Marinelli et al. | Novel multicharged silver (I)–NHC complexes derived from zwitterionic 1, 3-symmetrically and 1, 3-unsymmetrically substituted imidazoles and benzimidazoles: synthesis and cytotoxic properties | |
| Bustamante et al. | A study on the properties and reactivity of naphthoquinone–cobalt (III) prototypes for bioreductive prodrugs | |
| Kumar et al. | Designing, syntheses, characterization, computational study and biological activities of silver-phenothiazine metal complex | |
| Refaat et al. | Chemical and biological evaluation of moxifloxacin-benzimidazole mixed ligands complexes: Anti-cancer and anti-oxidant activities | |
| Milenković et al. | Synthesis, characterization and biological activity of three square-planar complexes of Ni (II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene] hydrazinecarboxylate and monodentate pseudohalides | |
| Kondratenko et al. | Synthesis, crystal structure and properties of copper (II) complexes with triethanolamine and carboxylic acids (succinic, salicylic, cinnamic) | |
| Gull et al. | Synthesis of Ni (II), Cu (II) and Co (II) complexes with new macrocyclic Schiff-base ligand containing dihydrazide moiety: Spectroscopic, structural, antimicrobial and antioxidant properties | |
| Đurić et al. | Silver (I) complexes with 1, 10-phenanthroline-based ligands: The influence of epoxide function on the complex structure and biological activity | |
| Farhan | Study on the interaction of copper (II) complex of morin and its antimicrobial effect | |
| Issa et al. | Synthesis, characterization, thermal, and antimicrobial studies of binuclear metal complexes of sulfa-guanidine Schiff bases | |
| Kalinowska-Lis et al. | Influence of selected inorganic counter-ions on the structure and antimicrobial properties of silver (I) complexes with imidazole-containing ligands | |
| Sumi et al. | Synthesis, spectroscopic investigation and bioactivities of metal complexes from curcuma longa derivative | |
| Kashar et al. | Synthesis, characterization, antimicrobial and anticancer activity of Zn (II), Pd (II) and Ru (III) complexes of dehydroacetic acid hydrazone | |
| Núñez et al. | A novel quinoline molecular probe and the derived functionalized gold nanoparticles: Sensing properties and cytotoxicity studies in MCF-7 human breast cancer cells | |
| Santos et al. | Silver (I) complexes with 2-acetylpyridinebenzoylhydrazones exhibit antimicrobial effects against yeast and filamentous fungi | |
| CN105524082A (en) | Synthesis and antibacterial activity of zinc voriconazole complex | |
| Li et al. | Synthesis and bioactive studies of complex 8-hydroxyquinolinato-bis-(salicylato) yttrium (III) | |
| Khor et al. | Schiff Bases and Their Copper (II) Complexes Derived from Cinnamaldehyde and Different Hydrazides: Synthesis and Antibacterial Properties | |
| CN107759491A (en) | Schiff bases copper（II）Anticancer complex and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160427 |