2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine hydrochloride

• ChemBase ID: 122734
• Molecular Formular: C19H22ClN5O4
• Molecular Mass: 419.86208
• Monoisotopic Mass: 419.13603189
• SMILES: c1(nc(c2c(n1)cc(c(c2)OC)OC)N)N1CCN(C(=O)c2occc2)CC1.Cl
• Canonical SMILES: COc1cc2nc(nc(c2cc1OC)N)N1CCN(CC1)C(=O)c1ccco1.Cl
• InChI: InChI=1S/C19H21N5O4.ClH/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14;/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22);1H
• InChIKey: WFXFYZULCQKPIP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine hydrochloride
• IUPAC Traditional name: 2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine hydrochloride; prazosin hydrochloride
• Synonyms: 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazine hydrochloride; Furazosin hydrochloride; Prazosin hydrochloride; [4-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl]-2-furanylmethanone Hydrochloride; 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonxyl)piperazine Hydrochloride; Adversuten; Adverszuten; Alpress LP; Furazosin; Lentopres; NSC 292810; Peripress; Prazosin Hydrochloride; (4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(furan-2-yl)methanone hydrochloride; Minipress; Vasoflex; Pressin and Hypovase; Prazosin HCl; 1-(4-氨基-6,7-二甲氧基-2-喹唑啉基)-4-(2-呋喃甲酰基)哌嗪 盐酸盐; 脉宁平 盐酸盐; 哌唑嗪 盐酸盐

Database IDs

• CAS Number: 19237-84-4
• EC Number: 242-903-4
• MDL Number: MFCD00058177
• Beilstein Number: 4303561
• PubChem SID: 24277793; 162217087
• PubChem CID: 68546

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.14705259
• LogD (pH = 7.4): 1.4251277
• Log P: 1.6505165
• Molar Refractivity: 104.4981 cm^3
• Polarizability: 39.320244 Å^3
• Polar Surface Area: 106.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dilute aqueous acid: insoluble; DMSO; H2O: soluble0.5 mg/mL; H2O: soluble1 mg/mL, clear, colorless; Methanol; methanol: soluble6 mg/mL
• Apperance: white; White Solid
• Melting Point: 276-278°C; 277-280 °C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: VA1350000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38-62
• Safety Statements: 28-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335-H361
• GHS Precautionary statements: P261-P281-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Target: Others
• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146)
• Mechanism of Action: Alpha 2B -Adrenoceptor antagonist,; Melatonin MT 3 -receptor antagonist

Product Information

• Purity: ≥99% (TLC); ≥99.0% (TLC)
• Salt Data: Free Base; HCl
• Impurities: ≤1% water
• Application(s): Antihypertensive agent
• Empirical Formula (Hill Notation): C19H21N5O4 · HCl

DETAILS

Sigma Aldrich - P115

Biochem/physiol Actions
α1- 和 α2Β-肾上腺素受体拮抗剂；MT3 褪黑激素受体拮抗剂。
General description
吸湿、光敏

Sigma Aldrich - P7791

Biochem/physiol Actions
Peripheral α1-adrenoceptor antagonist; vasodilator.
Caution
Hygroscopic; light sensitive.

Sigma Aldrich - 81515

Other Notes
An α1-adrenergic receptor antagonist. Suppresses experimental autoimmune encephalomyelitis in the Lewis rat1

Toronto Research Chemicals - P702325

An antihypertensive. α1-Adrenergic blocker.

REFERENCES

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• Honkanen, E. et al., J. Het. Chem., 1980, 17, 797, (synth, bibl)
• Cavero, I. et al., Life Sci., 1980, 27, 1525, (rev, pharmacol)
• Rawlins, M.D., Prazosin: Pharmacol., Hypertens. Congestive Heart Failure, (Ed.), Grune and Stratton, N.Y., 1981, (book)
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• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5260
• Kostek, L.J., Anal. Profiles Drug Subst., 1989, 18, 351, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 384
• Luchelli, A. et al., Br. J. Pharmacol., 1997, 121, 1775-1781, (pharmacol)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AJP000; FPP100