MINOCYCLINE
Conditions | Yield |
---|---|
With methanol; lithium hydroxide at 0 - 20℃; for 2h; Reagent/catalyst; | 93% |
[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
MINOCYCLINE
Conditions | Yield |
---|---|
With nitrous acid isobutyl ester In N,N-dimethyl-formamide at 70℃; for 0.75h; | 85% |
(dimethylamino)trimethyltin
[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
MINOCYCLINE
Conditions | Yield |
---|---|
dichlorobis(tri-O-tolylphosphine)palladium In toluene for 8h; Heating; | 68% |
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In N,N-dimethyl-formamide at 50℃; for 6h; Concentration; Reagent/catalyst; |
minocycline Hydrochloride
MINOCYCLINE
Conditions | Yield |
---|---|
With acetic acid In methanol at 42℃; for 3h; Temperature; Reagent/catalyst; Solvent; | 55.4% |
With sodium hydrogencarbonate In water pH=6.5 - 7.0; |
morpholine
(dimethylamino)trimethyltin
[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
A
MINOCYCLINE
Conditions | Yield |
---|---|
Stage #1: morpholine; (dimethylamino)trimethyltin In toluene Heating; Stage #2: [4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide; dichlorobis(tri-O-tolylphosphine)palladium In toluene for 24h; Heating; | A n/a B 42% |
1-methyl-piperazine
(dimethylamino)trimethyltin
[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
A
MINOCYCLINE
Conditions | Yield |
---|---|
Stage #1: 1-methyl-piperazine; (dimethylamino)trimethyltin In toluene Heating; Stage #2: [4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide; dichlorobis(tri-O-tolylphosphine)palladium In toluene for 24h; Heating; | A n/a B 40% |
azetidine
(dimethylamino)trimethyltin
[4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide
A
MINOCYCLINE
Conditions | Yield |
---|---|
Stage #1: azetidine; (dimethylamino)trimethyltin In toluene Heating; Stage #2: [4S-(4α,12aα)]-4-(dimethylamino)-3,10,12,12a-tetrahydroxy-7-iodo-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacene-2-carboxamide; dichlorobis(tri-O-tolylphosphine)palladium In toluene for 24h; Heating; Further stages.; | A 10% B 35% |
MINOCYCLINE
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water pH=8 - 9; | |
With sodium hydrogencarbonate In water pH=6.5 - 7; |
demeclocycline hydrochloride
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine; palladium on activated charcoal; hydrogen / ethanol 2: rhodium contaminated with carbon; hydrogen; toluene-4-sulfonic acid / methanol / -5 - 5 °C 3: sulfuric acid; N-iodo-succinimide / 2 h / 0 - 10 °C 4: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 6 h / 50 °C View Scheme |
6-demethyltetracycline
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: rhodium contaminated with carbon; hydrogen; toluene-4-sulfonic acid / methanol / -5 - 5 °C 2: sulfuric acid; N-iodo-succinimide / 2 h / 0 - 10 °C 3: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 6 h / 50 °C View Scheme |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sulfuric acid; potassium nitrate / 1 h / Cooling with ice 2: potassium hydroxide / 4 h / 100 °C / Sealed tube 3: sodium hydroxide; urea; 5%-palladium/activated carbon; hydrogen / water / 6 h / 20 °C / 5250.53 Torr / Autoclave 4: hydrogen; methanesulfonic acid; 5% rhodium-on-charcoal / N,N-dimethyl-formamide; methanol / 7 h / 50 °C / 5250.53 - 6000.6 Torr / Autoclave 5: nitrous acid isobutyl ester / N,N-dimethyl-formamide / 0.75 h / 70 °C View Scheme |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide / 4 h / 100 °C / Sealed tube 2: sodium hydroxide; urea; 5%-palladium/activated carbon; hydrogen / water / 6 h / 20 °C / 5250.53 Torr / Autoclave 3: hydrogen; methanesulfonic acid; 5% rhodium-on-charcoal / N,N-dimethyl-formamide; methanol / 7 h / 50 °C / 5250.53 - 6000.6 Torr / Autoclave 4: nitrous acid isobutyl ester / N,N-dimethyl-formamide / 0.75 h / 70 °C View Scheme |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; urea; 5%-palladium/activated carbon; hydrogen / water / 6 h / 20 °C / 5250.53 Torr / Autoclave 2: hydrogen; methanesulfonic acid; 5% rhodium-on-charcoal / N,N-dimethyl-formamide; methanol / 7 h / 50 °C / 5250.53 - 6000.6 Torr / Autoclave 3: nitrous acid isobutyl ester / N,N-dimethyl-formamide / 0.75 h / 70 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione; MINOCYCLINE With hydrogenchloride; sulfuric acid; trifluoroacetic acid at 40 - 50℃; Inert atmosphere; Stage #2: With monomethanolamine | 97% |
MINOCYCLINE
minocycline Hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 0 - 5℃; for 1h; pH=1 - 2; Solvent; | 92.7% |
N,N-phenylbistrifluoromethane-sulfonimide
MINOCYCLINE
10-trifluoromethylsulfonate-minocycline
Conditions | Yield |
---|---|
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; | 90% |
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran for 0.75h; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; for 3h; | |
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 0.666667h; Schlenk technique; Inert atmosphere; Stage #2: N,N-phenylbistrifluoromethane-sulfonimide With dmap In tetrahydrofuran Schlenk technique; Inert atmosphere; |
MINOCYCLINE
Conditions | Yield |
---|---|
Stage #1: MINOCYCLINE With mercury(II) diacetate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Stage #2: With dipotassium hydrogenphosphate; water; edetate disodium In N,N-dimethyl-formamide; acetonitrile at 0 - 5℃; for 0.583333h; | 87.5% |
MINOCYCLINE
Conditions | Yield |
---|---|
With mercury(II) diacetate; sodium hydroxide In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 20℃; for 1h; Molecular sieve; | 22% |
Conditions | Yield |
---|---|
Stage #1: MINOCYCLINE With potassium tert-butylate In tetrahydrofuran at -78 - 20℃; for 0.916667h; Schlenk technique; Inert atmosphere; Stage #2: methyl p-toluene sulfonate In tetrahydrofuran Schlenk technique; Inert atmosphere; Stage #3: trifluoroacetic acid In water; acetonitrile | 17.4% |
chloro-methylsulfanyl-methane
MINOCYCLINE
Conditions | Yield |
---|---|
(i) MeSO3H, (ii) Raney-Ni, aq. EtOH; Multistep reaction; |
MINOCYCLINE
C21H20N2O8(1-)
Conditions | Yield |
---|---|
With potassium hexacyanoferrate(III) In water pH 8.5 buffer; |
Conditions | Yield |
---|---|
With potassium hexacyanoferrate(III) In water Mechanism; Rate constant; Equilibrium constant; various pH; |
MINOCYCLINE
C21H19N2O8(2-)
Conditions | Yield |
---|---|
With potassium hexacyanoferrate(III) In water pH 14 buffer; |
Conditions | Yield |
---|---|
With MES buffer; dihydrogen peroxide; potassium iodide; porcine thyroid peroxidase In water at 22℃; for 0.133333h; pH=6.5; Kinetics; Product distribution; Further Variations:; Catalysts; Reagents; Temperatures; reaction time; Enzymatic reaction; |
MINOCYCLINE
(4S,4aS,5aR,12S)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxanaphthacene-2-carboxamide
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 0℃; for 1h; |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HNO3; H2SO4 / 1 h / 0 °C 2: H2 / Pd/C / 2068.59 Torr 3: Na2CO3 / tetrahydrofuran View Scheme |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HNO3; H2SO4 / 1 h / 0 °C 2: H2 / Pd/C / 2068.59 Torr 3: Na2CO3 / tetrahydrofuran View Scheme |
MINOCYCLINE
(4S,4aS,5aR,12aS)-9-(4-Bromo-butyrylamino)-4,7-bis-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HNO3; H2SO4 / 1 h / 0 °C 2: H2 / Pd/C / 2068.59 Torr 3: DMPU View Scheme |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HNO3; H2SO4 / 1 h / 0 °C 2: H2 / Pd/C / 2068.59 Torr 3: Na2CO3 / tetrahydrofuran View Scheme |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: HNO3; H2SO4 / 1 h / 0 °C 2: H2 / Pd/C / 2068.59 Torr 3: DMPU View Scheme |
MINOCYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HNO3; H2SO4 / 1 h / 0 °C 2: H2 / Pd/C / 2068.59 Torr 3: Na2CO3 / tetrahydrofuran View Scheme |
1. Introduction of Minocycline
Minocycline is one kind of light yellow irregular solid or bright yellow-orange amorphous solid. The IUPAC Name of this chemical is (2Z,4S,4aS,5aR,12aS)-2-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-10,11,12a-trihydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione. Besides, Minocycline belongs to antibiotics. In addition, its Classification Code is Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Drug / Therapeutic Agent; Human Data; Mutation data; Natural Product. Minocycline is the most lipid-soluble of the tetracycline-class antibiotics.
2. Properties of Minocycline
Physical properties about Minocycline are:
(1)Flash Point: 445.4 °C; (2)Boiling Point: 812.8 °C at 760 mmHg; (3)Enthalpy of Vaporization: 123.88 kJ/mol; (4)Vapour Pressure: 6.33E-28 mmHg at 25°C; (5)XLogP3: -0.6; (6)H-Bond Donor: 5; (7)H-Bond Acceptor: 9.
3. Structure Descriptors of Minocycline
(1)InChI: InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27-28,31,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17-,23-/m0/s1
(2)InChIKey: FFTVPQUHLQBXQZ-KVUCHLLUSA-N
(3)Canonical SMILES: CN(C)C1C2CC3CC4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C
(4)Isomeric SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3CC4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C
(5)Smiles: [C@@H]12[C@](C(=C3[C@H](C2)Cc2c(C3=O)c(ccc2N(C)C)O)O)(C(=O)C(=C([C@H]1N(C)C)O)C(=O)N)O
4. Toxicity of Minocycline
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
infant | TDLo | oral | 12mg/kg/2D-I (12mg/kg) | BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE GASTROINTESTINAL: NAUSEA OR VOMITING | Therapie. Vol. 38, Pg. 93, 1983. |
man | TDLo | oral | 343mg/kg/17W- (343mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" LIVER: LIVER FUNCTION TESTS IMPAIRED BLOOD: EOSINOPHILIA | American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996. |
mouse | LD50 | intracrebral | 38mg/kg (38mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: EXCITEMENT MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES | Chemotherapy Vol. 26, Pg. 196, 1980. |
mouse | LD50 | intraperitoneal | 310mg/kg (310mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978. | |
mouse | LD50 | intravenous | 140mg/kg (140mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978. | |
mouse | LD50 | oral | 3100mg/kg (3100mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 501, 1978. | |
women | TDLo | oral | 8mg/kg (8mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" | American Journal of Medicine. Vol. 109, Pg. 340, 2000. |
women | TDLo | oral | 28mg/kg/2W-I (28mg/kg) | BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)" BEHAVIORAL: HEADACHE SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE | Annals of Internal Medicine. Vol. 127, Pg. 168, 1997. |
women | TDLo | oral | 100mg/kg (100mg/kg) | KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS KIDNEY, URETER, AND BLADDER: HEMATURIA KIDNEY, URETER, AND BLADDER: PROTEINURIS | British Medical Journal. Vol. 1, Pg. 524, 1979. |
women | TDLo | oral | 112mg/kg/4W-I (112mg/kg) | LIVER: LIVER FUNCTION TESTS IMPAIRED SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996. |
women | TDLo | oral | 730mg/kg/1Y-I (730mg/kg) | BEHAVIORAL: ANOREXIA (HUMAN GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: LIVER FUNCTION TESTS IMPAIRED | American Journal of Gastroenterology. Vol. 91, Pg. 1641, 1996. |
women | TDLo | oral | 1204mg/kg/86W (1204mg/kg) | MUSCULOSKELETAL: JOINTS | British Journal of Rheumatology. Vol. 33, Pg. 674, 1994. |
women | TDLo | oral | 17520mg/kg/12 (17520mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE MUSCULOSKELETAL: CHANGES IN TEETH AND SUPPORTING STRUCTURES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Journal of Ophthalmology. Vol. 125, Pg. 396, 1998. |
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