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Gliquidone

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Name

Gliquidone

EINECS 251-463-2
CAS No. 33342-05-1 Density 1.34 g/cm3
PSA 130.26000 LogP 5.31900
Solubility N/A Melting Point 179 °C
Formula C27H33N3O6S Boiling Point N/A
Molecular Weight 527.642 Flash Point N/A
Transport Information N/A Appearance white powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 33342-05-1 (Gliquidone) Hazard Symbols N/A
Synonyms

AR-DF 26;ARDF 26SE;Beglynor;Glurenorm;

Article Data 73

Gliquidone Synthetic route

33456-68-7

4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonamid

3173-53-3

Cyclohexyl isocyanate

33342-05-1

gliquidone

Conditions
ConditionsYield
Stage #1: 4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonamid With potassium carbonate at 40℃; for 0.5h;
Stage #2: Cyclohexyl isocyanate at 90℃; for 4.5h; Reagent/catalyst; Temperature;
80%
33342-05-1

gliquidone

N-Cyclohexyl-N',N''-bis-<4-<2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonyl>guanidin

Conditions
ConditionsYield
With pyridine; p-toluenesulfonyl chloride Heating;81%
33342-05-1

gliquidone

33456-68-7

4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonamid

Conditions
ConditionsYield
With dmap; phthalic anhydride In pyridine for 5h; Reflux; Inert atmosphere;77%
With pyridine; dmap; phthalic anhydride for 5h; Inert atmosphere; Reflux;77%
With pyridine; dmap; phthalic anhydride for 4h; Inert atmosphere; Reflux;75%
33342-05-1

gliquidone

108-24-7

acetic anhydride

N-<4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonyl>acetamid

Conditions
ConditionsYield
With pyridine for 0.25h;71%
85-44-9

phthalic anhydride

33342-05-1

gliquidone

A

33456-68-7

4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonamid

B

2133-65-5

N-cyclohexylphthalimide

Conditions
ConditionsYield
With pyridine; dmap for 4h; Heating;A 46%
B 46%
33342-05-1

gliquidone

A

33456-68-7

4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonamid

B

2133-65-5

N-cyclohexylphthalimide

Conditions
ConditionsYield
With pyridine; dmap; phthalic anhydride for 4h; Heating;A 46%
B 46%
108-30-5

succinic acid anhydride

33342-05-1

gliquidone

N-<4-<2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl>benzolsulfonyl>succinimid

Conditions
ConditionsYield
With pyridine; dmap32%
33342-05-1

gliquidone

nickel(II) chloride hexahydrate

Ni(gliquidone)2Cl2

Conditions
ConditionsYield
In methanol MeOH soln. of metal salt added to gliquidone soln. with stirring, warmedto ca. 60°C; filtered, washed, dried; elem. anal.;

copper(II) choride dihydrate

33342-05-1

gliquidone

Cu(gliquidone)2Cl2

Conditions
ConditionsYield
In methanol MeOH soln. of metal salt added to gliquidone soln. with stirring, warmedto ca. 60°C; filtered, washed, dried; elem. anal.;

iron(III) chloride hexahydrate

33342-05-1

gliquidone

Fe(gliquidone)2Cl3

Conditions
ConditionsYield
In methanol MeOH soln. of metal salt added to gliquidone soln. with stirring, warmedto ca. 60°C; filtered, washed, dried; elem. anal.;

Gliquidone Specification

The Gliquidone, with the CAS registry number 33342-05-1 and EINECS registry number 251-463-2, has the IUPAC name of 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea. It belongs to the product categories of Active Pharmaceutical Ingredients and API. And the molecular formula of the chemical is C27H33N3O6S. What's more, it is an anti-diabetic drug in the sulfonylurea class, and always used in the treatment of diabetes mellitus type 2.

The physical properties of Gliquidone are as followings: (1)ACD/LogP: 3.11; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.94; (4)ACD/LogD (pH 7.4): 1.14; (5)ACD/BCF (pH 5.5): 9.23; (6)ACD/BCF (pH 7.4): 1.47; (7)ACD/KOC (pH 5.5): 79.48; (8)ACD/KOC (pH 7.4): 12.62; (9)#H bond acceptors: 9; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 112.68 Å2; (13)Index of Refraction: 1.624; (14)Molar Refractivity: 138.9 cm3; (15)Molar Volume: 393.2 cm3; (16)Polarizability: 55.06×10-24cm3; (17)Surface Tension: 62.7 dyne/cm; (18)Density: 1.34 g/cm3.

Uses of Gliquidone: It can react with acetic acid anhydride to produce N-{4-[2-(3,4-Dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isochinolyl)ethyl]benzolsulfonyl}acetamid. This reaction will need reagent pyridine. The reaction time is 15 minutes, and the yield is about 71%.    

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NC1CCCCC1)NS(=O)(=O)c2ccc(cc2)CCN4C(=O)c3c(ccc(OC)c3)C(C4=O)(C)C
(2)InChI: InChI=1/C27H33N3O6S/c1-27(2)23-14-11-20(36-3)17-22(23)24(31)30(25(27)32)16-15-18-9-12-21(13-10-18)37(34,35)29-26(33)28-19-7-5-4-6-8-19/h9-14,17,19H,4-8,15-16H2,1-3H3,(H2,28,29,33)
(3)InChIKey: LLJFMFZYVVLQKT-UHFFFAOYAT

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