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97322-87-7

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97322-87-7 Usage

Description

Rezulin was launched in Japan, the UK (subseqently withdrawn) and the US for treatment of type Ⅱ diabetes. Two approaches, four steps and six steps, converge on 6-acetoxy-2-(4-aminophenoxymethyl)-2,5,7,8-tetramethylchroman which can be elaborated in two steps to Rezulin. It is the first of a new class of thiazolidenediones for NIDDM that reduces glucose concentrations without effecting insulin secretion. It binds to peroxisome proliferator-activated receptor gamma (PPARγ) thus activating this nuclear receptor which then influences carbohydrate metabolism. This is accomplished by increasing insulin sensitivity by upregulating glucose transporter (Glut1 and/or Glut4) expression without affecting the number or affinity of insulin receptors. There is also an increase in hepatic glycogen synthase activity which enhances glucose utilization and a reduction in hepatic gluconeogenesis by inhibiting fructose-1 ,&bisphosphatase. Pancreatic islet cell destruction is prevented. It reduces serum triglycerides because PPARγ causes fibroblasts to differentiate into adipocytes and does not activate RARα. It has a half-life of 9 h and is metabolized into three compounds having no activity.

Chemical Properties

Crystalline Solid

Uses

Different sources of media describe the Uses of 97322-87-7 differently. You can refer to the following data:
1. Troglitazone is an an oral hypoglycemic agent which improves insulin sensitivity and decreases hepatic glucose production. Antidiabetic.
2. antidiabetic;peroxisome proliferator-activated receptors activator
3. Troglitazone is a TZD which was approved for the treatment of insulin resistance and hyperglycemia in Type II diabetes, under the trade name Resulin?, but was withdrawn from the market due to hepatotoxicity. Troglitazone is a potent and selective PPARγ agonist. The EC50 values for transactivation of human and mouse PPARγ in a cell-based assay are 0.55 and 0.78 μM, respectively. In the same assay system, no activation of PPARα and PPARδ was observed at concentrations up to 10 μM. Troglitazone binds to the PPARγ ligand-binding domain (LBD) but fails to induce interaction of the PPARγ LBD with the transcriptional coactivators SRC-1, TIF2, AIB1, p300, or TRAP220. Troglitazone also induces cell cycle arrest and apoptosis in several cancer cell lines with an EC50 of 10 μM.

Manufacturing Process

A mixture of 70 g of ethyl-3-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2- ylmethoxy)phenyl]-2-chloropropionate, 13.12 g of thiourea and 80.2 ml of sulpholane was reacted for 80 min, under a nitrogen stream at 115°-120°C. Subsequently, a 656.2 ml acetic acid, 218.7 ml conc. hydrochloric acid and 109.4 ml water was added to this and the resulting mixture was further heated for 12 h at 85°-90°C. The reaction mixture was cooled to room temperature and 196.8 g of sodium bicarbonate was added and once the evolution of carbondioxide had ceased, the solvent was distilled off applying high vacuum. A 10:1 by volume mixture of benzene and ethyl acetate was added to the residue and the crude product was washed with a mixture of equal volumes of a saturated aq. sodium bicarbonate solution water. The organic layer was dried over anhydrous sodium sulphate and the solvent was distilled off. The resulting crude product was quickly eluted from a silica gel column with 50% ethylacetate-hexane to furnish 40 g of the required 5-{4- (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)benzyl)thiazolidine-2,4- dione (Troglitazone) with a HPLC purity of about 67-70%. The elution of column was continued further to yield 5-[4-(6-hydroxy-2,5,7,8- tetramethylchroman-2-yl-methoxy)benzyl]-2-iminothiazolidine-4-one with HPLC purity of about 70%.

Brand name

Prelay (Sankyo); Rezulin (Pfizer);Ronglitazone.

General Description

A α-tocopherol (vitamin E) moiety containing thiazolidinedione class of insulin-sensitizer that acts as an activator of peroxisome proliferator-activated receptors γ (PPARγ). Also exhibits anti-proliferative and anti-inflammatory properties. Shown to induce cell cycle arrest and apoptosis in human hepatoma cells. Inhibits vascular smooth muscle cell (VSMC) migration by rapidly activating MEK/ERK pathway leading to the induction of c-fos and Ets-1 expression. Blocks PDGF-induced cell proliferation of pancreatic stellate and accelerates p21Cip1 turnover by inhibiting PKCδ signaling in VSMCs. Exerts positive inotropic effect via Ca2+ sensitization in the sarcoplasmic reticulum and inhibits Na+/H+ exchange activity and proliferation of macrovascular endothelial cells.

Biological Activity

Selective PPAR γ receptor agonist (EC 50 values are 780 and 555 nM at murine and human PPAR γ receptors respectively). Displays no activity at PPAR α or PPAR δ receptors. Antidiabetic agent; exerts potent glucose-lowering effects in insulin-resistant diabetic mice. Displays anti-invasive effect on human breast cancer cells; reduces migration, adhesion and spreading on fibronectin-coated plates. Also inhibits lamellipodia formation and actin polymerization.

Biochem/physiol Actions

Primary TargetPeroxisome proliferator-activated receptors γ (PPARγ)

in vitro

troglitazone pparγ ligands showed potent inhibitory effect on proliferation, and could induce rcc cell apoptosis, suggesting that the pparγ ligands have potential antitumor effects on renal carcinoma cells [1].

in vivo

troglitazone increased ec proliferation in brown and white adipose tissue and liver in mice at sarcomagenic doses (400 and 800 mg/kg) after four weeks of treatment [2].

References

γ1) Kodera et al. (2000) Ligand type-specific interactions of peroxisome proliferator-activated receptor gamma with transcriptional coactivators; J. Biol. Chem., 275 33201 2) Tchoukalova et al. (2000) Enhancing effect of troglitazone on porcine adipocyte differentiation in primary culture: a comparison with dexamethasone; Obes. Res., 8 664 3) Tsubouchi et al. (2000) Inhibition of human lung cancer cell growth by the peroxisome proliferator-activated receptor-gamma agonists through induction of apoptosis; Biochem. Biophys. Res. Commun.270 4) Wyttenbach & Kuentz (2017),?Glass-forming ability of compounds in marketed amorphous drug products; Eur. J. Pharm. and Biopharm.,?112?204 [Focus Citation]

Check Digit Verification of cas no

The CAS Registry Mumber 97322-87-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,7,3,2 and 2 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 97322-87:
(7*9)+(6*7)+(5*3)+(4*2)+(3*2)+(2*8)+(1*7)=157
157 % 10 = 7
So 97322-87-7 is a valid CAS Registry Number.
InChI:InChI=1/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)

97322-87-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Troglitazone

1.2 Other means of identification

Product number -
Other names Prelay

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:97322-87-7 SDS

97322-87-7Synthetic route

5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)benzylidene]-2,4-thiazolidinedione

5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)benzylidene]-2,4-thiazolidinedione

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
With sodium tetrahydroborate; dimethylaminoacetic acid; sodium hydroxide In tetrahydrofuran; water at 20℃;84%
With hydrogen; acetic acid In water; palladium
5-[4-(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-ylmethoxy)-benzyl]-thiazolidine-2,4-dione
199441-78-6

5-[4-(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-ylmethoxy)-benzyl]-thiazolidine-2,4-dione

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 70 - 80℃; debenzylation;70%
thiourea
17356-08-0

thiourea

Ethyl 3-<4-<(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>phenyl>-2-chloropropionate
97322-68-4

Ethyl 3-<4-<(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>phenyl>-2-chloropropionate

A

Troglitazone
97322-87-7

Troglitazone

B

5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one
97323-08-5

5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one

Conditions
ConditionsYield
With hydrogenchloride; acetic acid 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h; Yield given. Multistep reaction. Yields of byproduct given;
Troglitazone glucuronide
127040-01-1

Troglitazone glucuronide

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
enzymatic treatment using glusulase;
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C
2: AcOH; piperidine / toluene / 4 h / Heating
3: HCl / methanol / 0.25 h
4: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: imidazole / dimethylformamide
2: LAH / 3 h / 20 °C
3: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C
4: AcOH; piperidine / toluene / 4 h / Heating
5: HCl / methanol / 0.25 h
6: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: toluene-4-sulfonic acid / 12 h / Reflux
2: dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere
3: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
6: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
7: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
8: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme
(6-t-butyldimethylsilyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2yl)methanol
228114-44-1

(6-t-butyldimethylsilyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2yl)methanol

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C
2: AcOH; piperidine / toluene / 4 h / Heating
3: HCl / methanol / 0.25 h
4: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C
View Scheme
6-tert-butyl(dimethyl)silyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid
716320-66-0

6-tert-butyl(dimethyl)silyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: LAH / 3 h / 20 °C
2: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C
3: AcOH; piperidine / toluene / 4 h / Heating
4: HCl / methanol / 0.25 h
5: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C
View Scheme
4-[6-(tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethyl-chroman-2-ylmethoxy]-benzaldehyde
716320-67-1

4-[6-(tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethyl-chroman-2-ylmethoxy]-benzaldehyde

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: AcOH; piperidine / toluene / 4 h / Heating
2: HCl / methanol / 0.25 h
3: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C
View Scheme
5-[1-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethyl-chroman-2-ylmethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione

5-[1-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethyl-chroman-2-ylmethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / methanol / 0.25 h
2: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C
View Scheme
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

A

Troglitazone
97322-87-7

Troglitazone

B

PhCO-X

PhCO-X

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: t-BuOK / dimethylformamide / 1 h / 25 °C
1.2: 60 percent / dimethylformamide / 15 h / 25 °C
2.1: benzoic acid; piperidine / toluene / 4 h / 120 °C
3.1: 54 percent / Mg; MeOH / 8 h / 45 °C
4.1: 70 percent / HCl; AcOH / 70 - 80 °C
View Scheme
(6-Benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methanol
171270-07-8

(6-Benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methanol

A

Troglitazone
97322-87-7

Troglitazone

B

PhCO-X

PhCO-X

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: t-BuOK / dimethylformamide / 1 h / 25 °C
1.2: 60 percent / dimethylformamide / 15 h / 25 °C
2.1: benzoic acid; piperidine / toluene / 4 h / 120 °C
3.1: 54 percent / Mg; MeOH / 8 h / 45 °C
4.1: 70 percent / HCl; AcOH / 70 - 80 °C
View Scheme
4-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy]benzaldehyde
138564-69-9

4-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy]benzaldehyde

A

Troglitazone
97322-87-7

Troglitazone

B

PhCO-X

PhCO-X

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzoic acid; piperidine / toluene / 4 h / 120 °C
2: 54 percent / Mg; MeOH / 8 h / 45 °C
3: 70 percent / HCl; AcOH / 70 - 80 °C
View Scheme

A

Troglitazone
97322-87-7

Troglitazone

B

PhCO-X

PhCO-X

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 54 percent / Mg; MeOH / 8 h / 45 °C
2: 70 percent / HCl; AcOH / 70 - 80 °C
View Scheme
2-hydroxymethyl-2,5,7,8-tetramethyl-chroman-6-ol
79907-49-6

2-hydroxymethyl-2,5,7,8-tetramethyl-chroman-6-ol

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) NaH / 1.) DMF, rt, 1 h, 2.) benzene, rt, 1 h
2: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h
3: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C
4: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
5: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
6: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
7: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme
2-hydroxymethyl-6-methoxymethoxy-2,5,7,8-tetramethylchroman
107188-55-6

2-hydroxymethyl-6-methoxymethoxy-2,5,7,8-tetramethylchroman

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h
2: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C
3: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
4: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
5: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
6: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme
6-Hydroxy-2,5,7,8-tetramethyl-2-<(4-nitrophenoxy)methyl>chroman
107188-58-9

6-Hydroxy-2,5,7,8-tetramethyl-2-<(4-nitrophenoxy)methyl>chroman

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
2: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
3: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
4: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme
6-acetoxy-2-[(4-aminophenoxy)methyl]-2,5,7,8-tetramethylchromane
107188-37-4

6-acetoxy-2-[(4-aminophenoxy)methyl]-2,5,7,8-tetramethylchromane

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
2: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme
2,5,7,8-tetramethyl-6-acetoxy-2-(4-nitrophenyloxy)methylchroman
118070-83-0

2,5,7,8-tetramethyl-6-acetoxy-2-(4-nitrophenyloxy)methylchroman

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
2: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
3: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme
6-(Methoxymethoxy)-2,5,7,8-tetramethyl-2-<(4-nitrophenoxy)methyl>chroman
118070-84-1

6-(Methoxymethoxy)-2,5,7,8-tetramethyl-2-<(4-nitrophenoxy)methyl>chroman

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C
2: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
3: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
4: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
5: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme
(+/-)-5-<4-(6-hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-ylmethoxy)benzyl>thiazolidine-2,4-dione
107187-56-4

(+/-)-5-<4-(6-hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-ylmethoxy)benzyl>thiazolidine-2,4-dione

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
In methanol; palladium
2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

Ethyl 3-<4-<(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>phenyl>-2-chloropropionate
97322-68-4

Ethyl 3-<4-<(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>phenyl>-2-chloropropionate

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
With hydrogenchloride; thiourea In sulfolane
carbonic acid tert-butyl ester 2-{4-[2,4-dioxo-thiazolidin-(5Z)-ylidenemethyl]phenoxymethyl}-2,5,7,8-tetramethyl-chroman-6-yl ester
1375483-15-0

carbonic acid tert-butyl ester 2-{4-[2,4-dioxo-thiazolidin-(5Z)-ylidenemethyl]phenoxymethyl}-2,5,7,8-tetramethyl-chroman-6-yl ester

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
2: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme
carbonic acid tert-butyl ester 2-{4-[2,4-dioxothiazolidin-5-ylmethyl]phenoxymethyl}-2,5,7,8-tetramethylchroman-6-yl ester
1375483-24-1

carbonic acid tert-butyl ester 2-{4-[2,4-dioxothiazolidin-5-ylmethyl]phenoxymethyl}-2,5,7,8-tetramethylchroman-6-yl ester

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
With hydrogenchloride; water In acetonitrile for 0.75h; Reflux;
C20H27F3O7S

C20H27F3O7S

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
2: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
3: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
4: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme
6-tert-butoxycarbonyloxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid ethyl ester
1375483-09-2

6-tert-butoxycarbonyloxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid ethyl ester

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
3: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
4: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
5: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
6: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme
carbonic acid tert-butyl ester 2-hydroxymethyl-2,5,7,8-tetramethyl-chroman-6-yl ester
1375483-11-6

carbonic acid tert-butyl ester 2-hydroxymethyl-2,5,7,8-tetramethyl-chroman-6-yl ester

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
3: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
4: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
5: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme
carbonic acid tert-butyl ester 2-(4-formylphenoxymethyl)-2,5,7,8-tetramethyl-chroman-6-yl ester
1375483-13-8

carbonic acid tert-butyl ester 2-(4-formylphenoxymethyl)-2,5,7,8-tetramethyl-chroman-6-yl ester

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
2: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
3: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme
ethyl 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylate
53174-07-5

ethyl 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylate

Troglitazone
97322-87-7

Troglitazone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
5: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
6: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
7: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme
acetic anhydride
108-24-7

acetic anhydride

Troglitazone
97322-87-7

Troglitazone

benzene
71-43-2

benzene

5-<4-<(6-Acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>benzyl>-2,4-thiazolidinedione benzene monoadduct

5-<4-<(6-Acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>benzyl>-2,4-thiazolidinedione benzene monoadduct

Conditions
ConditionsYield
With pyridine for 48h; Ambient temperature;80%
Troglitazone
97322-87-7

Troglitazone

3-PyCO-X

3-PyCO-X

5-[4-(2,5,7,8-tetramethyl-6-nicotinoyloxychroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione
97323-02-9

5-[4-(2,5,7,8-tetramethyl-6-nicotinoyloxychroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Conditions
ConditionsYield
75%
succinic acid anhydride
108-30-5

succinic acid anhydride

Troglitazone
97322-87-7

Troglitazone

succinic acid mono-{2-[4-(2,4-dioxo-thiazolidin-5-ylmethyl)-phenoxymethyl]-2,5,7,8-tetramethyl-chroman-6-yl} ester

succinic acid mono-{2-[4-(2,4-dioxo-thiazolidin-5-ylmethyl)-phenoxymethyl]-2,5,7,8-tetramethyl-chroman-6-yl} ester

Conditions
ConditionsYield
With dmap In dichloromethane for 48h; Reflux;63%
With pyridine at 85℃; for 6h;
With pyridine In cyclohexane
Troglitazone
97322-87-7

Troglitazone

PhCO-X

PhCO-X

5-[4-(6-benzoyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione
97323-01-8

5-[4-(6-benzoyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Conditions
ConditionsYield
62%
Troglitazone
97322-87-7

Troglitazone

PrCO-X

PrCO-X

5-[4-(6-butyryloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione
97323-00-7

5-[4-(6-butyryloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Conditions
ConditionsYield
56%
Troglitazone
97322-87-7

Troglitazone

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester
7355-18-2

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 2,3,4-tri-O-acetyl-1-O-<2-<4-<2,4-dioxothiazolidin-5-ylmethyl>phenoxymethyl>-2,5,7,8-tetramethylchroman-6-yl>-β-D-glucopyranuronate
127040-00-0

methyl 2,3,4-tri-O-acetyl-1-O-<2-<4-<2,4-dioxothiazolidin-5-ylmethyl>phenoxymethyl>-2,5,7,8-tetramethylchroman-6-yl>-β-D-glucopyranuronate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In nitrobenzene at 85℃; under 20 Torr; for 4h;23%
Troglitazone
97322-87-7

Troglitazone

Troglitazone glucuronide
127040-01-1

Troglitazone glucuronide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 23 percent / p-toluenesulfonic acid monohydrate / nitrobenzene / 4 h / 85 °C / 20 Torr
2: 100 percent / 2.4percent aq.NaOH / methanol / 1 h / Ambient temperature
View Scheme
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

Troglitazone
97322-87-7

Troglitazone

Di-t-butyl α,α'-{5-[4-(6-t-butoxycarbonylmethoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl ]-2,4-dioxothiazolidine-3,5-diyl}diacetate
107187-69-9

Di-t-butyl α,α'-{5-[4-(6-t-butoxycarbonylmethoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl ]-2,4-dioxothiazolidine-3,5-diyl}diacetate

Conditions
ConditionsYield
With potassium carbonate In acetone

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