(S)-2-ETHOXY-3-[4-[2-(4-METHANESULFONYLOXY-PHENYL)-ETHOXY]-PHENYL]-PROPIONIC ACID
(S)-2-ETHOXY-3-[4-[2-(4-METHANESULFONYLOXY-PHENYL)-ETHOXY]-PHENYL]-PROPIONIC ACID Basic information
- Product Name:
- (S)-2-ETHOXY-3-[4-[2-(4-METHANESULFONYLOXY-PHENYL)-ETHOXY]-PHENYL]-PROPIONIC ACID
- Synonyms:
-
- 2-Ethoxy-3-{4-[2-(4-methanesulfonyloxy-phenyl)-ethoxy]-phenyl}-propionicacid
- (αS)-α-Ethoxy-4-[2-[4-[(Methylsulfonyl)oxy]phenyl]ethoxy]benzenepropanoic Acid
- (alphaS)-alpha-Ethoxy-4-[2-[4-[(methylsulfonyl)oxy]phenyl]ethoxy]benzenepropanoic acid
- (S)-2-ethoxy-3-[4-(2-{4-Methanesulphonyloxyphenyl}ethoxy)phenyl]propanoic acid
- (S)-2-Ethoxy-3-(4-(4-((Methylsulfonyl)oxy)phenethoxy)phenyl)propanoic acid
- Benzenepropanoic acid, .alpha.-ethoxy-4-[2-[4-[(methylsulfonyl)oxy]phenyl]ethoxy]-, (.alpha.S)-
- (S)-2-ETHOXY-3-[4-[2-(4-METHANESULFONYLOXY-PHENYL)-ETHOXY]-PHENYL]-PROPIONIC ACID
- TESAGLITAZAR
- CAS:
- 251565-85-2
- MF:
- C20H24O7S
- MW:
- 408.47
- Product Categories:
-
- Drug Intermediates
- Intermediates & Fine Chemicals
- Chiral Reagents
- Pharmaceuticals
- Sulfur & Selenium Compounds
- Mol File:
- 251565-85-2.mol
(S)-2-ETHOXY-3-[4-[2-(4-METHANESULFONYLOXY-PHENYL)-ETHOXY]-PHENYL]-PROPIONIC ACID Chemical Properties
- Melting point:
- 83-85°C
- Boiling point:
- 611℃
- Density
- 1.278
- Flash point:
- 324℃
- storage temp.
- 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 3.62±0.10(Predicted)
- color
- White
- Merck
- 14,9177
(S)-2-ETHOXY-3-[4-[2-(4-METHANESULFONYLOXY-PHENYL)-ETHOXY]-PHENYL]-PROPIONIC ACID Usage And Synthesis
Chemical Properties
White Solid
Uses
Dual -acting peroxisome proliferator-activated receptor (PPAR) a and agonist. Antidiabetic
Biological Activity
Tesaglitazar is a potent and specific dual PPARα/γ agonist th at improves insulin resistance and carbohydrate and lipid metabolism in ob/ob mice and obese Zucker rats.
Synthesis
123-91-1
251565-89-6
142-82-5
251565-85-2
The general procedure for the synthesis of (S)-2-ethoxy-3-{4-[2-(4-methylsulfonylphenyl)ethoxy]phenyl}propionic acid from 1,4-dioxane, the compound (CAS: 251565-89-6) and n-heptane was as follows: (S)-2-ethoxy-3-{4-[2-{4-methanesulfonylphenyl)ethoxy]phenyl}propionic acid was synthesized by mixing (S)-2-ethoxy-N-(2-hydroxy(R)-1-phenylethyl)-3-[4-[2-{4-methanesulfonyloxy phenyl}ethoxy)phenyl]propionamide (4.49 g, 8.59 mmol), concentrated sulfuric acid (12.5 mL), 1,4-dioxane (50 mL), and water (50 mL) were stirred at 80 °C for 6 hours. After the reaction was completed, it was cooled to room temperature, water (100 mL) was added and the product was extracted with dichloromethane (2 x 100 mL). The organic phases were combined, washed with brine (60 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The product was purified by silica gel column chromatography using gradient elution with n-heptane:ethyl acetate:acetic acid (10:10:1, v/v/v) as eluent, and finally distilled by azeotropic distillation through toluene to afford (S)-2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid (2.78 g, 79% yield). The product was structurally confirmed by 1H-NMR (600 MHz, DMSO-d6) and 13C-NMR (150 MHz, DMSO-d6).
in vivo
Tesaglitazar (0.3-10 μmol/kg; po; once daily; 104 weeks) induces subcutaneous stromal sarcomas (fibrosarcomas) in Wistar Hannover Galas rats, and also induces a variety of non-neoplastic changes, such as cardiac hypertrophy and liver changes[1].
Tesaglitazar (1, 10 μmol/kg; po; once daily; 2 or 12 weeks) in Wistar Hannover Galas rats, sustained stimulation of DNA synthesis, increased BrdU-labeled cells[1].
Tesaglitazar (50 nmol/kg; sc; once daily; 14 days) reduced body weight, food intake, fasting blood glucose and insulin levels, improved insulin sensitivity and glucose metabolism, and had no significant effect on renal function in the male C57BL/6J diet-induced obesity (DIO) mouse model[2].
Tesaglitazar (5 or 100 nmol/kg; sc; single dose) induced an acute deterioration in glucose tolerance at a high dose (100 nmol/kg), but a low dose (5 nmol/kg) reduced body weight, food intake and fasting blood glucose levels and improved glucose tolerance[2] in the DIO mouse model[2].
Tesaglitazar (10-20 μg/kg; intraperitoneal injection; single dose) significantly restored the mechanical paw withdrawal threshold (PWT) in the Streptozotocin (HY-13753)-induced diabetic neuropathy pain model in rats without affecting blood glucose levels[3].
| Animal Model: | Wistar Hannover Galas rats (6-8 weeks old; carcinogenicity model)[1] |
| Dosage: | 0.3, 1, 3, 10 μmol/kg (dissolved in 5mM sodium hydrogen carbonate buffer solution, pH 8.5) |
| Administration: | Oral gavage, once daily, 104 weeks |
| Result: | Induced subcutaneous mesenchymal sarcomas (fibrosarcomas) in both male and female rats (10 μmol/kg). Caused various non-neoplastic changes, such as myocardial hypertrophy, liver changes, and alterations in multiple organ systems. |
storage
Desiccate at RT
References
[1] Patent: US6258850, 2001, B1
(S)-2-ETHOXY-3-[4-[2-(4-METHANESULFONYLOXY-PHENYL)-ETHOXY]-PHENYL]-PROPIONIC ACIDSupplier
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