- Doxazosin
- Doxazosin hydrochloride
- Doxazosin mesylate
- 74192-47-5Benzoicacid, 4-amino-3-cyano-
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Cas Database |
| Name |
Doxazosin |
EINECS | N/A |
| CAS No. | 74191-85-8 | Density | 1.371 g/cm3 |
| PSA | 175.02000 | LogP | 2.88670 |
| Solubility | N/A | Melting Point |
289-290 °C |
| Formula | C23H25N5O5 | Boiling Point | 718 °C at 760 mmHg |
| Molecular Weight | 451.482 | Flash Point | 388 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | Risk Codes | R23/24/25; R34; R40; R43; R36/37/38; R38 | |
| Molecular Structure |
|
Hazard Symbols |
 T, Xi
|
| 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; |
Article Data | 9 |
Doxazosin Synthetic route
- 23680-84-4
2-chloro-6,7-dimethoxyquinazolin-4-amine
- 70918-00-2
(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone
- 74191-85-8
doxazosin
| Conditions | Yield |
|---|---|
| In butan-1-ol Reflux; | 88% |
| In butan-1-ol for 5h; Heating; | 83% |
- 3663-80-7, 34385-93-8, 70918-53-5, 70918-54-6
1,4-benzodioxane-2-carboxylic acid
- 60547-97-9
4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline
- 74191-85-8
doxazosin
| Conditions | Yield |
|---|---|
| With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 5.16667h; | 80% |
- 4739-94-0
ethyl 2,3-dihydro-1,4-benzodioxin-2-carboxylate
- 74191-85-8
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 |
- 120-80-9
benzene-1,2-diol
- 74191-85-8
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 |
- 1246188-97-5
(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(1H-imidazol-1-yl)methanone
- 60547-97-9
4-amino-6,7-dimethoxy-2-piperazin-1-ylquinazoline
- 74191-85-8
doxazosin
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at 25 - 28℃; Product distribution / selectivity; |
- 3663-80-7, 34385-93-8, 70918-53-5, 70918-54-6
1,4-benzodioxane-2-carboxylic acid
- 74191-85-8
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 |
- 3663-82-9
2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin
- 74191-85-8
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 |
- 533-58-4
2-Iodophenol
- 74191-85-8
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 |
- 74191-85-8
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 |
- 74191-85-8
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 |
Doxazosin Specification
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.
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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
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