CS264198B1 - 3-/5-nitro-2-furyl/propenylisothiocyanat and process for preparing them - Google Patents
3-/5-nitro-2-furyl/propenylisothiocyanat and process for preparing them Download PDFInfo
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- CS264198B1 CS264198B1 CS878911A CS891187A CS264198B1 CS 264198 B1 CS264198 B1 CS 264198B1 CS 878911 A CS878911 A CS 878911A CS 891187 A CS891187 A CS 891187A CS 264198 B1 CS264198 B1 CS 264198B1
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- furyl
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- propenylisothiocyanate
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- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 3- (5-nitro-2-furyl) propenylisothiocyanate Chemical compound 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- WRASENKOWNCZKM-UHFFFAOYSA-N C1=C(OC(=C1)[N+](=O)[O-])CC=CBr Chemical compound C1=C(OC(=C1)[N+](=O)[O-])CC=CBr WRASENKOWNCZKM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004332 silver Substances 0.000 claims abstract description 4
- 229910052709 silver Inorganic materials 0.000 claims abstract description 4
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- NNQDMQVWOWCVEM-UHFFFAOYSA-N 1-bromoprop-1-ene Chemical compound CC=CBr NNQDMQVWOWCVEM-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 230000002051 biphasic effect Effects 0.000 claims 1
- 235000010216 calcium carbonate Nutrition 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- FIMJSWFMQJGVAM-UHFFFAOYSA-N chloroform;hydrate Chemical compound O.ClC(Cl)Cl FIMJSWFMQJGVAM-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000011181 potassium carbonates Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 241000894006 Bacteria Species 0.000 abstract description 2
- 230000000842 anti-protozoal effect Effects 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYEMDAZVNKCOHK-UHFFFAOYSA-N 1-isothiocyanatoprop-1-ene Chemical compound CC=CN=C=S RYEMDAZVNKCOHK-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000195619 Euglena gracilis Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000223892 Tetrahymena Species 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
3-(5-nitro-2-íuryl)propenylizotiokyanát a sposob jeho přípravy. Podstata spósobu přípravy 3-(5-mtro-2-furyl)propenylizotiokyanátu spočívá v tom, že sa 3-(5-nitro-2-furyl)- propenylbromid pósobením urotropínu prevedie na 3-(5-nitro-2-furyl)propenylamín- -hydrochlorid, z ktorého sa pósobením tiofosgénu za přítomnosti zásady připraví produkt. Další sposob přípravy spočívá v pósobení rodanidu strieborného alebo olovnatého na 3-(5-nitro-2-furyl)propenylbromid a 3- (5-nitro-2 furyljpropenylizotiokyanát sa chromatograficky oddělí od vedlajšieho produktu, 3- (5-nitro-2-furyl) propenyltiokyanátu. Zlúčenina vykazuje biologickú účinnost na baktérie a má antiprotozoálnu účinnost. Tiež najde využitie pri přípravě nových 3- - (5-nitro-2-furyl) propenylových derivátov. 3-(5-nitro-2-furyl)propenylizotiokyanát je charakterizovaný vzorcom 1.3- (5-nitro-2-furyl) propenylisothiocyanate a way of its preparation. The nature of the method of preparation 3- (5-methyl-2-furyl) propenylisothiocyanate is that 3- (5-nitro-2-furyl) - propenylbromide is converted by urotropin to 3- (5-nitro-2-furyl) propenylamine- the hydrochloride from which the thiophosgene acts product in the presence of a base. Another method of preparation is to act silver or lead acid rodanide to 3- (5-nitro-2-furyl) propenyl bromide a 3- (5-nitro-2 furylpropenylisothiocyanate is Chromatographically separate from the by-product 3- (5-nitro-2-furyl) propenyl thiocyanate. The compound exhibits biological activity bacteria and has antiprotozoal efficacy. It also finds use in preparing new 3- - (5-nitro-2-furyl) propenyl derivatives. 3- (5-nitro-2-furyl) propenylisothiocyanate is characterized by formula 1.
Description
Vynález sa týká 3-(5-nitro-2-furyl)propenylizokyanátu vyznačujúceho sa biologickou aktivitou a sposobu jeho přípravy.The present invention relates to 3- (5-nitro-2-furyl) propenyl isocyanate characterized by biological activity and a process for its preparation.
V literatuře je len velmi málo odkazov týkajúcich sa přípravy 3-(5-nitro-2-furyl)propenylových derivátov. Z dostupnej literatury je známa syntéza 3-(5-nitro-2-furyl jpropenylalkoholu a niekotkých jeho esterov (M. J. Berklava, S. Hillers: Latvijas PSR Zinatnu Akad. Vestis 3, 349 [1963]) studium literatury ukázalo, že 3-(5-nitro-2-furyl)propenylizotiokyanát nebol doteraz připravený.There are very few references in the literature regarding the preparation of 3- (5-nitro-2-furyl) propenyl derivatives. From the available literature, the synthesis of 3- (5-nitro-2-furyl) propenyl alcohol and some of its esters is known (MJ Berklava, S. Hillers: Latvijas PSR Zinatnu Akad. Vestis 3, 349 [1963]). 5-Nitro-2-furyl) propenylisothiocyanate has not been prepared yet.
Predmetom vynálezu je 3-(5-nitro-2-furyl)propenylizotiokyanát vzorcaThe present invention provides 3- (5-nitro-2-furyl) propenylisothiocyanate of the formula
O2N-^y~CH^ CH- CHZ-NCS íl)„ a sposoby jeho přípravy.O 2 N- (γ-CH 2 CH-CH 2 -NCS III) and methods for its preparation.
Podstata sposobu přípravy 3-(5-nitro-2-furyljpropenylizotlokyanátu spočívá v tom, že na 3-(5-nitro-2-f uryl jpropenylbromid (známy z čs. autorského osvedčenia č. 264191 sa vo vodnom etanole posobí urotropínom a na vzniknutý 3-(5-nitro-2-furyl)propenylamín-hydrochlorid sa posobí tiofosgénom v prostředí vody a chloroformu pri teplote 0 až 30 °C v přítomnosti zásady s výhodou v přítomnosti uhličitanu vápenatého. Reakcia prebieha podl'a schémy:The essence of the process for preparing 3- (5-nitro-2-furyl) -propenylisotloocyanate is to provide 3- (5-nitro-2-furyl) propenyl bromide (known from the Czech Certificate of Authorization No. 264191 with urotropin in aqueous ethanol and the resulting The 3- (5-nitro-2-furyl) propenylamine hydrochloride is impregnated with thiophosgene in water and chloroform at a temperature of 0 to 30 ° C in the presence of a base, preferably in the presence of calcium carbonate.
O?N CH s CH' CHÍ + (CH2.k HCI (g)O? N CH CH s' i + CH (CH 2.K HCl (g)
ON CH^CH-CH^NH^ hci £· 0 s—y Ce.C03 o N-< CH=CH-CH?-NH.. HCí + CSCt ~ >ON CH? CH-CH? NH? Hc? O? S? Y Ce.C0 3 o N- <CH = CH-CH ? -NH 2 HCl + CSCl 2
** - ΟΛ N CH=CH-C H<NC S** - Ο Λ N CH = CH-CH <NC S
OO
Další sposob přípravy 3-(5-nitr o-2-f uryl)propenylizotiokyanátu podta vynálezu spočívá v tom, že na 3-(5-nitro-2-furyl jpropenylbromid sa posobí rodanidom strieborným, alebo rodanidom olovnatým v prostředí benzenu pri teplotách 20 až 80 °C. Zmes produktov 3- (5-nitro-2-f uryl j propenylizotiokyanát a 3- (5-nitr o-2-f uryl jpropenyltiokyanát sa rozdělí na chromatografickej koloně na silikageli, pričom ako eluent možno použit benzen, chloroform, chlorid uhličitý s výhodou chloroformu.A further process for preparing 3- (5-nitro-2-furyl) propenyl isothiocyanate according to the invention is to treat 3- (5-nitro-2-furyl) propenyl bromide with silver rodanide or lead rodanide in benzene at 20 ° C. The product mixture of 3- (5-nitro-2-furyl) propenylisothiocyanate and 3- (5-nitro-2-furyl) propenylthiocyanate is separated on a silica gel column using benzene, chloroform as eluent. , carbon tetrachloride, preferably chloroform.
Reakcia prebieha podta schémy:The reaction follows the scheme:
iVCH = CH-C8r + Ag-SCNO^NCH=CH~CΗΛ-NCS + + OzN-^y-CH=CH-CHz-SCNiVCH = CH-C8r + Ag SCNO ^ NCH = CH ~ -NCS CΗ Λ + O ^ y from N-CH = CH of -SCN
Výhody spůsobu přípravy 3-(5-nitro-2-furyljpropenylizotiokyanátu podta vynálezu spočívajú okrem iného v tom, že jeho příprava nie je komplikovaná a je z dostupných surovin.The advantages of the process according to the invention for the preparation of 3- (5-nitro-2-furyl) propenylisothiocyanate are, inter alia, that its preparation is not complicated and is made from available raw materials.
Nasledujúce příklady bližšie ilustrujú, ale neobmedzujú spůsob přípravy zlúčeniny podta vynálezu.The following examples illustrate but do not limit the preparation of the compound of the invention.
Příklad 1Example 1
K roztoku 4,6 g (0,02 molu) 3-(5-nitro-2-furyl)propenylbromidu v 20 ml etanolu sa přidá 2,82 g (0,02 molu) urotropínu v 80 ml vody. Reakčná zmes sa zahrieva do varu 1 hodinu. Po ochladení na laboratórnu teplotu sa do zmesi zavádza intenzívny prúd plynného (g) chlorovodíku. Zmes sa samovolné zahřeje a po ukončení zavádzania HC1 (g) sa za tepla přefiltruje a odpaří do sucha. Vzniknutý 3- (5-nitro-2-f uryl) propenylamín-hydrochlorid sa rozpustí v 200 ml vody a přidá sa do zmesi 2,3 g (0,02 molu) tiofosgénu, 2,2 g (0,022 molu) uhličitanu vápenatého a 80 ml chloroformu pri teplote 5 až 10 °C. Reakčná zmes sa mieša 4 h pri laboratorně] teplote. Po ukončení reakcie sa oddělí organická vrstva, vodná vrstva sa extrahuje 3 X 25 ml chloroformu. Spojené organické vrstvy sa premyjú vodou a vysušia chloridom vápenatým. Po odpaření rozpúštadla sa surový produkt krystalizuje z heptánu.To a solution of 4.6 g (0.02 mol) of 3- (5-nitro-2-furyl) propenyl bromide in 20 ml of ethanol was added 2.82 g (0.02 mol) of urotropin in 80 ml of water. The reaction mixture is heated to boiling for 1 hour. After cooling to room temperature, an intense stream of gaseous (g) hydrogen chloride is introduced into the mixture. The mixture is self-heated and upon completion of the HCl (g) introduction, filtered hot and evaporated to dryness. The resulting 3- (5-nitro-2-furyl) propenylamine hydrochloride was dissolved in 200 ml of water and added to a mixture of 2.3 g (0.02 mol) of thiophosgene, 2.2 g (0.022 mol) of calcium carbonate and 80 ml of chloroform at 5-10 ° C. The reaction mixture was stirred at room temperature for 4 h. After completion of the reaction, the organic layer was separated, the aqueous layer was extracted with 3 X 25 mL of chloroform. The combined organic layers were washed with water and dried with calcium chloride. After evaporation of the solvent, the crude product is crystallized from heptane.
Výťažok 2,5 g (80 %).Yield 2.5 g (80%).
Příklad 2Example 2
Zmes 1,15 g (0,005 molu) 3-(5-nitro-2-furyljpropenylbromidu, 0,83 g (0,005 molu) rodanidu strieborného v 100 ml benzenu sa zahrieva 1 h do varu. Po ukončení reakcie sa odfiltruje bromid strieborný a benzenový roztok sa odpaří do sucha. Vznikajúce 3-(5-nitro-2-furyl)propenylizotiokyanát a 3-(5-nitro-2-furyl)propenyltiokyanát sa rozdelia na. chromatografickej kolóne plnenej silikagelom, eluent benzen. Poměr izomérov: 3-(5-nitro-2-furyl)propenylizotiokyanát 67 % a 3-(5-nitro-2-furyl)propenyltiokyanát 33%.A mixture of 1.15 g (0.005 mol) of 3- (5-nitro-2-furyl) propenyl bromide, 0.83 g (0.005 mol) of silver rodanide in 100 ml of benzene was heated to boiling for 1 h. The resulting 3- (5-nitro-2-furyl) propenylisothiocyanate and 3- (5-nitro-2-furyl) propenylthiocyanate are separated on a silica gel column, eluent benzene, isomer ratio: 3- ( 5-nitro-2-furyl) propenyl isothiocyanate 67% and 3- (5-nitro-2-furyl) propenylthiocyanate 33%.
Výťažok 0,9 g (86 %).Yield 0.9 g (86%).
Sumárny vzorec slúčeniny je C8H6N2O3S.The general formula of the compound is C 8 H 6 N 2 O 3 S.
Molekulová hmotnost je 210,21 a t. t. 78 stupňov Celzia.The molecular weight is 210.21 and has a melting point of 78 degrees Celsius.
Elementárma analýza: vypočítanéElemental analysis: calculated
13,32 %N, 15,22 % S nájdenéN, 13.22. Found: S, 15.22
13,15 %N, 15,20 % SN, 13.15. S, 15.20
Štruktúra 3-(5-nitro-2-furyl)propenylizotiokyanátu bola dokázaná IČ a 1H NMR spektroskopiou. IC spektrá sa merali na spektrometri UR-20 (fy Zeiss Jena) v chloroforme koncentrácia 102 molu. IC spektrum 3-(5-nitro-2-furyl)propenyllzotiokyanátu vykazuje tieto charakteristické pásy:The structure of 3- (5-nitro-2-furyl) propenylisothiocyanate was shown by IR and 1 H NMR spectroscopy. IC spectra were measured on a UR-20 spectrometer (Zeiss Jena) in chloroform at 10 2 mol. The IC spectrum of 3- (5-nitro-2-furyl) propenyl isothiocyanate shows the following characteristic bands:
γ (C—H) = 952 cm-1 »s (C—O—C) = 1005 cm-; vs (NO2) == 1 338 cm-1 i>as (NO2) = 1 503 cm1 v (NCS) = 2 080 cm1 XH NMR spektrum sa meralo na spektrometri BS 487 C (fy Tesla Brno) v. deuterovanom chloroforme, interný standard tetrametylsilán.γ (C-H) = 952 cm-1 "s (C-O-C) = 1005 cm-; vs (NO2) == 1338 cm -1 and> as (NO2) = 1503 cm 1 (NCS) = 2080 cm 1 X H-NMR spectrum was measured on a spectrometer BS 487 C (from Tesla Brno) in. deuterated chloroform, internal standard tetramethylsilane.
Η HΗ H
O.N CH—CH—CH2—-NCSO.N CH — CH — CH2 — NCS
(. '^0(. '^ 0
CH2 dublet 4,41 ppmCH2 doublet 4.41 ppm
Ηλ = Hb singlet 6,55 ppm fH3 dublet 6,53 ppmB λ = H b singlet 6.55 ppm f H3 doublet 6.53 ppm
H4 dublet 7,4 ppmH4 doublet 7.4 ppm
Výsledky testov ukázali, že 3-(5-nitro-2-furyljpropenylizotiokyanát podl'a vynálezu vykazuje nevýrazná bakteriocídnu účinnost a vysokú antiprotozoálnu účinnost. Výsledky screeningu ma niektoré kmene baktérií, a prvokov sú zhrnuté v tabulke 1.The results of the tests showed that the 3- (5-nitro-2-furyl) propenylisothiocyanate according to the invention shows low bacteriocidal activity and high antiprotozoal activity.The screening results have some strains of bacteria and protozoa are summarized in Table 1.
Tabulka 1Table 1
Názov kmeňa Minimálna inhibičná koncentrácia (^g/disk)Strain name Minimum inhibitory concentration (^ g / disc)
Bacillus subtilis 50Bacillus subtilis 50
Staphylococcus aureus —Staphylococcus aureus -
Streptococcus faecalis —Streptococcus faecalis -
Escherichia coli 50Escherichia coli
Próteus vulgaris 200Proteus vulgaris 200
Tetrahymena pyroformis 3,1Tetrahymena pyroformis 3.1
Euglena gracilis 3,1Euglena gracilis 3.1
Vzhladom k tomu, že 3-(5-nitro-2-furyl)propenylizotiokyanát podlá vynálezu je zlúčenina dobře rozpustná v organických rozpúšťadlách a reaktívna voči nukleofilným činidlám, sprístupňuje syntézu nových 3-(5-nltro-2-furyl)propenylových derivátov s předpokládanou biologickou účinnosťou.Since the 3- (5-nitro-2-furyl) propenylisothiocyanate of the present invention is well soluble in organic solvents and reactive to nucleophilic reagents, it makes available the synthesis of new 3- (5-nitro-2-furyl) propenyl derivatives with the predicted biological efficacy.
Claims (3)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS878911A CS264198B1 (en) | 1987-12-07 | 1987-12-07 | 3-/5-nitro-2-furyl/propenylisothiocyanat and process for preparing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS878911A CS264198B1 (en) | 1987-12-07 | 1987-12-07 | 3-/5-nitro-2-furyl/propenylisothiocyanat and process for preparing them |
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| Publication Number | Publication Date |
|---|---|
| CS891187A1 CS891187A1 (en) | 1988-10-14 |
| CS264198B1 true CS264198B1 (en) | 1989-06-13 |
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| CS878911A CS264198B1 (en) | 1987-12-07 | 1987-12-07 | 3-/5-nitro-2-furyl/propenylisothiocyanat and process for preparing them |
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| CN113651720B (en) * | 2021-09-14 | 2022-08-05 | 西安交通大学 | A kind of substituted alkenyl thiocyanate compound and preparation method thereof |
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