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CAS No.: | 85441-61-8 |
---|---|
Name: | Quinapril |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C25H30N2O5 |
Molecular Weight: | 438.524 |
Synonyms: | 3-Isoquinolinecarboxylicacid,2-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-,[3S-[2[R*(R*)],3R*]]-;Ectren;Koretic; |
EINECS: | 1312995-182-4 |
Density: | 1.217 g/cm3 |
Melting Point: | 120-130 °C |
Boiling Point: | 662 °C at 760 mmHg |
Flash Point: | 354.1 °C |
Appearance: | white solid |
Safety: | 22-24/25 |
PSA: | 95.94000 |
LogP: | 2.89590 |
L-Tic-OH
N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine
L-alanine acid chloride
quinapril
Conditions | Yield |
---|---|
With benzenesulfonamide; phosphorus pentachloride; triethylamine In n-heptane; dichloromethane; water | 83.9% |
tert-butyl (S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
quinapril
Conditions | Yield |
---|---|
With trifluoroacetic acid for 1h; Ambient temperature; |
quinapril hydrochloride
A
quinapril
B
<3S-<2(R*),3α,11aβ>>-1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino<1,2-b>isoquinoline-2-acetic acid, ethyl ester
Conditions | Yield |
---|---|
With citric acid at 80℃; pH=2.60; Kinetics; Further Variations:; pH-values; |
quinapril benzyl ester
quinapril
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal | |
With hydrogenchloride; hydrogen; 5%-palladium/activated carbon In water; acetone at 35 - 40℃; under 367.786 Torr; for 5h; Product distribution / selectivity; |
[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine
quinapril
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: triphenylphosphine / CH2Cl2 / 0.75 h 1.2: 45 percent / CH2Cl2 / 2.5 h / 25 - 30 °C 2.1: triethylamine / CH2Cl2 / 4 h / -15 - -10 °C 3.1: hydrogen / Pd/C View Scheme |
N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester
quinapril
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / CH2Cl2 / 4 h / -15 - -10 °C 2: hydrogen / Pd/C View Scheme |
L-Tic-OH
quinapril
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2SO4 / dioxane / 17 h / Ambient temperature 2: 78 percent / Et3N, DCC, 1-hydroxybenzotriazole / tetrahydrofuran / Ambient temperature 3: TFA / 1 h / Ambient temperature View Scheme |
(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester
quinapril
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / Et3N, DCC, 1-hydroxybenzotriazole / tetrahydrofuran / Ambient temperature 2: TFA / 1 h / Ambient temperature View Scheme |
N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride
quinapril
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 78 percent / Et3N, DCC, 1-hydroxybenzotriazole / tetrahydrofuran / Ambient temperature 2: TFA / 1 h / Ambient temperature View Scheme |
quinapril
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; 5%-palladium/activated carbon In ethanol; water at 35 - 40℃; under 367.786 Torr; for 5h; Product distribution / selectivity; |
The IUPAC name of Quinapril is (3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid. With the CAS registry number 85441-61-8, it is also named as 3-Isoquinolinecarboxylic acid, 2-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-, (3S-(2(R*(R*)),3R*))-. The classification codes are Angiotensin-Converting Enzyme Inhibitors, Antihypertensive Agents, Cardiovascular Agents, Enzyme Inhibitors and Protease Inhibitors. People should not breathe dust and avoid contact with skin and eyes.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.13; (4)ACD/LogD (pH 7.4): 0.76; (5)ACD/BCF (pH 5.5): 7.33; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.62; (8)ACD/KOC (pH 7.4): 1.49; (9)#H bond acceptors: 7; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.577; (13)Molar Refractivity: 119.51 cm3; (14)Molar Volume: 360.1 cm3; (15)Polarizability: 47.37×10-24 cm3; (16)Surface Tension: 52.2 dyne/cm; (17)Enthalpy of Vaporization: 102.32 kJ/mol; (18)Vapour Pressure: 2E-18 mmHg at 25°C; (19)Rotatable Bond Count: 10; (20)Exact Mass: 438.215472; (21)MonoIsotopic Mass: 438.215472; (22)Topological Polar Surface Area: 95.9; (23)Heavy Atom Count: 32.
Uses of Quinapril: It is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used in the treatment of hypertension and congestive heart failure. Contraindications: 1. Pregnancy; 2. Impaired renal and liver function; 3. Patients with a history of angioedema related to; 4. previous treatment with an ACE inhibitor; 5. Hypersensitive to Quinapril.
People can use the following data to convert to the molecule structure.
1. SMILES: O=C(OCC)[C@@H](N[C@H](C(=O)N2[C@H](C(=O)O)Cc1c(cccc1)C2)C)CCc3ccccc3;
2. InChI: InChI=1/C25H30N2O5/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30)/t17-,21-,22-/m0/s1.