ethyl bromide
6,7-methylenedioxy-4(1H)-oxo-cinnolin-3-carboxylic acid ethylester
Aliquat 336
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide; potassium carbonate In water; toluene |
cinoxacin
ethanol
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Reflux; | 92.9% |
cinoxacin
dimethyl sulfoxide
B
{Ni(1-ethyl-1,4-dihydro-4-oxo(1,3)dioxolo(4,5-g)cinnoline-3-carboxylate)2(H2O)2}
Conditions | Yield |
---|---|
With NaOH; H2O In dimethyl sulfoxide mixing DMSO soln. of cinoxacin and of the Ni salt, slow addn. of 5 ml of aq. NaOH with stirring, crystn. of Ni(cinoxacinate)2*2H2O after 1 d; filtration, washing (water), drying at 90°C, crystn. of the Ni complex contg. dimethyl sulfoxide ligands after 2-3 months from the remaining soln., filtration, drying at room temp., elem. anal.; | A 10% B 80% |
cinoxacin
1,2,3-Benzotriazole
3-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-1-ethyl-[1,3]dioxolo[4,5-g]cinnolin-4(1H)-one
Conditions | Yield |
---|---|
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 25℃; for 0.5h; Stage #2: cinoxacin In dichloromethane at 25℃; for 2h; | 80% |
Conditions | Yield |
---|---|
With NaOH; H2O In dimethyl sulfoxide mixing of a DMSO soln. of cinoxacin and of ZnCl2, addn. of 1 ml of aq. NaOH with stirring, pptn. of Zn(cinoxacinate)2*4H2O after 12-14 d; filtration, washing (water), drying at 90°C, remaining soln. standing at room temp., crystn. of the Zn complex (contg. additionally DMSO ligands) after a few d, filtration, drying at room temp., elem. anal.; | A 75% B 6% |
cinoxacin
1-ethyl-5-nitro-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnolin-3-carboxylic acid
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 0 - 20℃; for 13h; Inert atmosphere; | 75% |
cinoxacin
methanol
methyl 1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnolin-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: cinoxacin With boron tribromide In dichloromethane at -30 - 20℃; for 41h; Inert atmosphere; Stage #2: methanol In dichloromethane at -30 - 20℃; Inert atmosphere; | 74.5% |
cinoxacin
A
1-Ethyl-1H-[1,3]dioxolo[4,5-g]cinnolin-4-one
Conditions | Yield |
---|---|
With oxygen In methanol for 12h; Ambient temperature; Irradiation; in PBS-solution (pH=8); Yields of byproduct given; | A n/a B 62% |
With oxygen In methanol for 12h; Mechanism; Product distribution; Ambient temperature; Irradiation; Iin PBS-solution (pH=8); | |
With oxygen In methanol for 12h; Ambient temperature; Irradiation; in PBS-solution (pH=8); Yields of byproduct given; | A 0.580 mol B n/a |
cinoxacin
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
water
toluene
Conditions | Yield |
---|---|
With NaOCH3 In methanol; chloroform byproducts: NaCl; addn. of sodium methylate to soln. of ruthenium compd. and sodium nalidixicate in CHCl3/methanol (1/1), refluxing for 6 h; filtration through celite, addn. of toluene, keeping at room temp. with slow evapn. for 3 d, isolation of crystals, washing with hexane, elem. anal.; | 55% |
cinoxacin
1-ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carbonitrile
Conditions | Yield |
---|---|
Stage #1: cinoxacin With polyphosphate ester; ammonia In chloroform at 119 - 123℃; for 24h; Stage #2: With polyphosphate ester at 120℃; for 1h; | 21% |
cinoxacin
dimethyl sulfoxide
Conditions | Yield |
---|---|
With NaOH In dimethyl sulfoxide mixing DMSO solns. of cinoxacin (0.4 mmol) and CdCl2*2.5H2O (0.1 mmol); slow addn. of NaOH (0.1 M) with continuous stirring;; slow evapn. at room temp.; crystn. after 2-3 mo; elem. anal.;; | 12% |
cinoxacin
5-ethyl-5H-[1,3]dioxolo[4,5-f]indole-6,7-dione
Conditions | Yield |
---|---|
In formic acid; water (electrochemical reduction); |
cinoxacin
2-mercaptoethylamine hydrochloride
1-Ethyl-N-(2-mercaptoethyl)-6,7-methylene-dioxy-4(1H)-oxocinnoline-3-carboxamide
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide |
cinoxacin
1-Ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid, methyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In methanol; water |
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide In water; dimethyl sulfoxide Co(ClO4)2*6H2O mixed with cinoxacin; soln. NaOH added with stirring for1 h; filtered; washed (DMSO); dreid in vac. at 50°C to const. wt.; elem. anal.; powd. XRD; TG-DTA; |
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide In water; dimethyl sulfoxide cinoxacin mixed with Cu(NO3)2*3H2O; NaOH added with stirring; ppt. filtered; washed (DMSO); dried in vac. at 50°C; elem. anal.; powd. XRD, TG-DTA; |
cinoxacin
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water cinoxacin mixed with Ni(ClO4)2*6H2O; NaOH added with stirring; evapn. at room temp. for several d; filtered; washed (methanol); dried in vac. at 50°C; elem. anal.; powd. XRD, TG-DTA; |
Conditions | Yield |
---|---|
With NaOH In ethanol; water addn. of freshly prepared soln. of histamine in ethanol to aq. soln. of copper salt, addn. of an aq. soln. of cinoxacin with NaOH; cooling overnight, filtration, cooling filtrate in refrigerator for 7- 8months; elem. anal.; |
cinoxacin
Conditions | Yield |
---|---|
In methanol stoich. amts., warm solvent; pptn. on standing for few d, collection (filtration); single crystals fro mother liquor on slow evapn.; |
Conditions | Yield |
---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
cinoxacin
1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)cinnolin-4(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere 6.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 1.5 h / 20 °C / Inert atmosphere View Scheme |
cinoxacin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: thionyl chloride / dichloromethane / 1 h / Inert atmosphere; Reflux View Scheme |
cinoxacin
1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydrocinnolin-3-carboxamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: thionyl chloride / dichloromethane / 1 h / Inert atmosphere; Reflux 5.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Cooling with ice View Scheme |
cinoxacin
1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(piperidin-1-ylmethyl)cinnolin-4(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: boron tribromide / dichloromethane / 41 h / -30 - 20 °C / Inert atmosphere 1.2: -30 - 20 °C / Inert atmosphere 2.1: potassium carbonate; potassium iodide / acetone / Inert atmosphere; Reflux 3.1: potassium hydroxide / methanol; water / 1.5 h / Inert atmosphere; Reflux 3.2: 20 °C / pH 1 / Inert atmosphere 4.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / Cooling with ice; Inert atmosphere 5.2: Inert atmosphere View Scheme |
cinoxacin
5-amino-1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnolin-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid; potassium nitrate / 13 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid / 5 h / 2585.81 Torr / Inert atmosphere View Scheme |
cinoxacin
3-carboxy-1-ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnolin-5-diazonium chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sulfuric acid; potassium nitrate / 13 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid / 5 h / 2585.81 Torr / Inert atmosphere 3: hydrogenchloride; sodium nitrite / water / 5 h / 45 °C / Inert atmosphere View Scheme |
cinoxacin
5-chloro-1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnolin-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sulfuric acid; potassium nitrate / 13 h / 0 - 20 °C / Inert atmosphere 2: hydrogenchloride; palladium on activated charcoal; hydrogen; acetic acid / 5 h / 2585.81 Torr / Inert atmosphere 3: hydrogenchloride; sodium nitrite / water / 5 h / 45 °C / Inert atmosphere 4: sulfuric acid / 20 h / 95 °C / Inert atmosphere View Scheme |
Product Name: Cinoxacin (CAS NO.28657-80-9)
Molecular Formula: C12H10N2O5
Molecular Weight: 262.22g/mol
Mol File: 28657-80-9.mol
Einecs: 249-133-8
Appearance: Light tan crystals
Boiling point: 517.2 °C at 760 mmHg
Density: 1.64 g/cm3
Surface Tension: 65.7 dyne/cm
Enthalpy of Vaporization: 83.11 kJ/mol
Vapour Pressure: 1.61E-11 mmHg at 25°C
XLogP3-AA: 2.1
H-Bond Donor: 1
H-Bond Acceptor: 7
Product Categories: Interferes with DNA SynthesisAntibiotics; Quinolones and FluoroquinolonesMore...Close...; A - KAntibiotics; Antibacterial; Antibiotics A to; Antibiotics A-FAntibiotics; Antibiotics by Application; Antineoplastic and Immunosuppressive AntibioticsAntibiotics; Chemical Structure Class; Inhibits an EnzymeAntibiotics; Mechanism of Action; Spectrum of Activity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 850mg/kg (850mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 28(Suppl, |
mouse | LD50 | oral | 2330mg/kg (2330mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 28(Suppl, |
mouse | LD50 | subcutaneous | 900mg/kg (900mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Chemotherapy Vol. 28(Suppl, |
rat | LD50 | intravenous | 860mg/kg (860mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 28(Suppl, |
rat | LD50 | oral | 3610mg/kg (3610mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 28(Suppl, |
rat | LD50 | subcutaneous | 1380mg/kg (1380mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Chemotherapy Vol. 28(Suppl, |
Moderately toxic by ingestion, subcutaneous and intravenous routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Cinoxacin ,its CAS NO. is 28657-80-9,the synonyms is 1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid;cinoxacin ; Timtec-bb sbb003082 ; 1-Ethyl-6,7-methylenedioxy-4(1h)-oxocinnoline-3-carboxylicacid ; 3)Dioxolo(4,5-g)cinnoline-3-carboxylicacid,1,4-dihydro-1-ethyl-4-oxo-( ; Cinobac ; 1-Ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid .
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