74772-77-3

Basic information

• Product Name: CIGLITAZONE
• Synonyms: 5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-4-thiazolidinedione;U-63287;(+/-)-5-[4-(1-METHYLCYCLOHEXYLMETHOXY)BENZYL]-THIAZOLIDINE-2,4-DIONE;5-[[4-[(1-METHYLCYCLOHEXYL)METHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE;ADD 3878;CIGLITAZONE;CIGLITIZONE;CIGLITLZONE
• CAS NO: 74772-77-3
• Molecular Formula: C₁₈H₂₃NO₃S
• Molecular Weight: 333.45
• Product Categories: Active Pharmaceutical Ingredients;Metal Isotopes;Sulfur & Selenium Compounds;API's;Intracellular receptor
• Mol File: 74772-77-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 130-131°C
• Boiling Point: 504.5 °C at 760 mmHg
• Flash Point: 258.9 °C
• Appearance: white cyrstalline solid
• Density: 1.189 g/cm³
• Vapor Pressure: 2.65E-10mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: Store at RT
• Solubility: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml).
• PKA: 6.36±0.50(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: CIGLITAZONE(CAS DataBase Reference)
• NIST Chemistry Reference: CIGLITAZONE(74772-77-3)
• EPA Substance Registry System: CIGLITAZONE(74772-77-3)

Safety Data

• WGK Germany: 3
• RTECS: XJ5813700
• Hazardous Substances Data: 74772-77-3(Hazardous Substances Data)

Usage

Description

Ciglitazone, with the chemical formula (74772-77-3), is a potent PPARγ agonist characterized by an EC50 value of 3 μM. It is known for its ability to stimulate adipogenesis in human mesenchymal stem cells and possesses cell permeable properties. Additionally, Ciglitazone has been observed to inhibit HUVEC differentiation and angiogenesis, making it a significant compound in various biological and medical research applications.

Uses

Used in Pharmaceutical Research:
Ciglitazone is utilized as a selective PPARγ agonist for studying its antihyperglycemic activity, particularly in genetically obese mice. This application aids in understanding the compound's potential role in managing and treating diabetes and related metabolic disorders.
Used in Cell Biology Research:
In the field of cell biology, Ciglitazone serves as a valuable tool to investigate its effects on cell proliferation in human melanocytes. This application is crucial for exploring the role of PPARγ in skin pigmentation and related conditions.
Used in Dermatological Studies:
Ciglitazone is applied as a PPARγ agonist to study its impact on pigmentation and migration of human melanocytes. This research is vital for understanding the mechanisms underlying skin color variation and the development of pigmentary disorders.
Used in Cancer Research:
Ciglitazone may also be employed to study its effects on the cell cycle and apoptosis in monocytic cells. This application is essential for investigating the compound's potential role in cancer therapy and the prevention of tumor growth.

Biological Activity

Selective agonist at PPAR γ (peroxisome proliferator-activated receptor γ ). Activates PPAR γ with an EC 50 value of 3 μ M in vitro , and is at least 33-fold selective over PPAR α and δ . Antihyperglycemic in vivo .

Biochem/physiol Actions

Ciglitizone belongs to the class of thiazolidinediones and is a peroxisome proliferator-activated receptor γ (PPARγ) agonist. It exhibits anti-diabetic activity. Ciglitizone has the potential to treat tumor necrosis factor α (TNFα)-related apoptosis-inducing ligand (TRAIL)-refractory high-grade urothelial cancers.

References

1) Cantello et al. (1994) [[omega-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents; J. Med. Chem. 37 3977 2) Xin et al. (1999) Peroxisome proliferator-activated receptor gamma ligands are potent inhibitors of angiogenesis in vitro and in vivo; J. Biol. Chem. 274 9116

InChI:InChI=1/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)

Upstream product

• 85010-76-0 methyl (+)-3-<4-(1-methylcyclohexylmethoxy)phenyl>-(2S)-2-thiocyanatopropionate 
• 85003-07-2 methyl 2-chloro-3-<4-(1-methylcyclohexylmethoxy)phenyl>propionate 
• 196079-42-2 Δ2CG 
• 85002-76-2 4-(1-methylcyclohexylmethoxy)nitrobenzene 
• 887406-96-4 4-(1-Methyl-cyclohexylmethoxy)-phenylamine 
• 100-00-5 4-chlorobenzonitrile 
• 14064-13-2 (1-methylcyclohexyl)methanol 
• 17356-08-0 thiourea 
• 85010-78-2 2-bromo-3-<4-(1-methylcyclohexylmethoxy)phenyl>propionitrile 
• 85010-66-8 2-imino-5-<4-(1-methylcyclohexylmethoxy)benzyl>thiazolidin-4-one 

Downstream Products

• 96207-26-0 (+)-(5R)-<4-(1-methylcyclohexylmethoxy)benzyl>-2,4-thiazolidinedione 1-phenylethylamine salt 
• 96207-24-8 (-)-(5S)-<4-(1-methylcyclohexylmethoxy)benzyl>-2,4-thiazolidinedione 1-phenylethylamine salt 
• 96207-27-1 (+/-)-3-methyl-5-<4-(1-methylcyclohexylmethoxy)benzyl>-2,4-thiazolidinedione 

Relevant articles and documents

NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF

The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.

Thiazolidine derivatives

Thiazolidine derivatives of the general formula: STR1 [wherein R1 is alkyl, cycloalkyl, phenylalkyl, phenyl, a five- or six-membered heterocyclic group including one or two hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur or a group of the formula STR2 (where R3 and R4 are the same or different and each is lower alkyl or R3 and R4 are combined to each other either directly or as interrupted by a hetero-atom selected from the group consisting of nitrogen, oxygen and sulfur to form a five- or six-membered ring); R2 means a bond or a lower alkylene group; L1 and L2 are the same or different and each is lower alkyl or L1 and L2 are combined to form an alkylene group, provided that when R1 is other than alkyl, L1 and L2 may further be hydrogen, respectively] are novel compounds and useful as, for example, remedies for diabetes, hyperlipemia and so on of mammals including human beings.