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CAS No.: | 74191-85-8 |
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Name: | [4-(4-Amino-6,7-dimethoxy-quinazolin-2- yl)piperazin-1-yl]-(2,5-dioxabi cyclo[4.4.0]deca-6,8,10-trien-4-yl)methanone |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C23H25N5O5 |
Molecular Weight: | 451.482 |
Synonyms: | Piperazine,1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]-(9CI);[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](2,3-dihydro-1,4-benzodioxin-2-yl)methanone;Doxazosine;UK 33274;piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]-;2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)pipérazin-1-yl]-6,7-diméthoxyquinazolin-4-amine; |
Density: | 1.371 g/cm3 |
Melting Point: | 289-290 °C |
Boiling Point: | 718 °C at 760 mmHg |
Flash Point: | 388 °C |
Hazard Symbols: | T,Xi |
Risk Codes: | R23/24/25; R34; R40; R43; R36/37/38; R38 |
PSA: | 175.02000 |
LogP: | 2.88670 |
2-chloro-6,7-dimethoxyquinazolin-4-amine
(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone
doxazosin
Conditions | Yield |
---|---|
In butan-1-ol Reflux; | 88% |
In butan-1-ol for 5h; Heating; | 83% |
1,4-benzodioxane-2-carboxylic acid
4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline
doxazosin
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 5.16667h; | 80% |
ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate
doxazosin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 65 percent / 6 h / 70 - 80 °C 2: 83 percent / butan-1-ol / 5 h / Heating View Scheme |
benzene-1,2-diol
doxazosin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / potassium hydroxide; polyethylene glycol-400; potassium carbonate / toluene / 3.75 h / Heating 2: 65 percent / 6 h / 70 - 80 °C 3: 83 percent / butan-1-ol / 5 h / Heating View Scheme |
(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(1H-imidazol-1-yl)methanone
4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline
doxazosin
Conditions | Yield |
---|---|
In tetrahydrofuran at 25 - 28℃; Product distribution / selectivity; |
1,4-benzodioxane-2-carboxylic acid
doxazosin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 - 25 °C 2: tetrahydrofuran / 25 - 28 °C View Scheme | |
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: butan-1-ol / Reflux View Scheme |
2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin
doxazosin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; potassium permanganate / water / 0 °C 2: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium hydroxide; potassium permanganate / water / 0 °C 2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 4: butan-1-ol / Reflux View Scheme |
2-Iodophenol
doxazosin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 4: potassium hydroxide; potassium permanganate / water / 0 °C 5: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide; water; ethyl acetate / 24 h / 50 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 3: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 4: potassium hydroxide; potassium permanganate / water / 0 °C 5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 7: butan-1-ol / Reflux View Scheme |
doxazosin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 3: potassium hydroxide; potassium permanganate / water / 0 °C 4: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 6 h / 0 °C 2: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 3: potassium hydroxide; potassium permanganate / water / 0 °C 4: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 6: butan-1-ol / Reflux View Scheme |
doxazosin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 2: potassium hydroxide; potassium permanganate / water / 0 °C 3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 5.17 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 90 °C / Sealed tube; Inert atmosphere 2: potassium hydroxide; potassium permanganate / water / 0 °C 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane / -15 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 5: butan-1-ol / Reflux View Scheme |
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The Doxazosin, with the CAS registry number 74191-85-8, has the systematic name of [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](2,3-dihydro-1,4-benzodioxin-2-yl)methanone. Its classification codes are: Adrenergic Agents; Adrenergic Antagonists; Adrenergic alpha-antagonists; Antihypertensive agents; Cardiovascular Agents; Neurotransmitter Agents. The molecular formula of this chemical is C23H25N5O5.
The physical properties of Doxazosin are as following: (1)ACD/LogP: 0.65; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.33; (4)ACD/LogD (pH 7.4): 0.6; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.65; (7)ACD/KOC (pH 5.5): 5.62; (8)ACD/KOC (pH 7.4): 48.37; (9)#H bond acceptors: 10; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 89.49 Å2; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 121.23 cm3; (15)Molar Volume: 329.2 cm3; (16)Polarizability: 48.06×10-24cm3; (17)Surface Tension: 64.9 dyne/cm; (18)Density: 1.371 g/cm3; (19)Flash Point: 388 °C; (20)Enthalpy of Vaporization: 104.92 kJ/mol; (21)Boiling Point: 718 °C at 760 mmHg; (22)Vapour Pressure: 1.83E-20 mmHg at 25°C.
Preparation of Doxazosin: It can be prepared by 4-Amino-2-chloro-6,7 -dimethoxy-quinazoline and 2-(1-carboxymethyl piperazine carbonyl)-1,4-Benzodioxan.
Uses of Doxazosin: It is used to treat high blood pressure and urinary retention associated with benign prostatic hyperplasia. It is a kind of alpha-1 adrenergic receptor blocker that inhibits the binding of norepinephrine to the alpha-1 receptors on the membrane of vascular smooth muscle cells. And this primary effect of the inhibition is relaxed vascular smooth muscle tone, which decreases peripheral vascular resistance, leading to decreased blood pressure.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4Oc5c(OC4)cccc5
(2)InChI: InChI=1/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
(3)InChIKey: RUZYUOTYCVRMRZ-UHFFFAOYAW