1-{2-[4-(2-phenyl-1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}but-1-en-1-yl)phenoxy]ethyl}pyrrolidine

• ChemBase ID: 154100
• Molecular Formular: C34H42N2O2
• Molecular Mass: 510.70948
• Monoisotopic Mass: 510.32462859
• SMILES: CC/C(=C(/c1ccc(cc1)OCCN1CCCC1)\c1ccc(cc1)OCCN1CCCC1)/c1ccccc1
• Canonical SMILES: CC/C(=C(/c1ccc(cc1)OCCN1CCCC1)\c1ccc(cc1)OCCN1CCCC1)/c1ccccc1
• InChI: InChI=1S/C34H42N2O2/c1-2-33(28-10-4-3-5-11-28)34(29-12-16-31(17-13-29)37-26-24-35-20-6-7-21-35)30-14-18-32(19-15-30)38-27-25-36-22-8-9-23-36/h3-5,10-19H,2,6-9,20-27H2,1H3
• InChIKey: XQQWCGJGUHJSLR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[4-(2-phenyl-1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}but-1-en-1-yl)phenoxy]ethyl}pyrrolidine
• IUPAC Traditional name: 1-{2-[4-(2-phenyl-1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}but-1-en-1-yl)phenoxy]ethyl}pyrrolidine
• Synonyms: 1,1′-[(2-Phenyl-1-buten-1-ylidene)bis(4,1-phenyleneoxy-2,1-ethanediyl)]bis-pyrrolidine; Ridaifen-B

Database IDs

• CAS Number: 886465-70-9
• MDL Number: MFCD11114395
• PubChem SID: 162248239
• PubChem CID: 11548000

CALCULATED PROPERTIES

• Molar Refractivity: 167.9951 cm^3
• Polarizability: 61.921078 Å^3
• Polar Surface Area: 24.94 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.6703884
• LogD (pH = 7.4): 3.8996856
• Log P: 7.0237904

PROPERTIES

Physical Property

• Solubility: DMSO: ≥13 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37/38-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C34H42N2O2

DETAILS

Sigma Aldrich - R5030

Biochem/physiol Actions
Ridaifen-B (RID-B) is a novel tamoxifen (TAM) analog that significantly augments apoptosis-inducing effect of TAM in estrogen receptor (ER)-negatives cells. Ridaifen-B induces mitochondria-involved apoptosis in Jurkat cells, as evidenced by chromatin-condensed cells as well as downstream activation of caspases (caspase-3, -8 and -9) in a dose- and time-dependent manner. At 4 hours of incubation, IC50 for RID-B is 4 muM (30 muM for TAM). And at prolonged treatment of 48 hours, IC50 for RID-B is 0.1 muM.1 In a related report2 on the global anti-tumor activity, RID-B strongly inhibits 39 human cancer cells (JFCR 39), both ER-+ or ER-- at concentrations of equal or less than 1muM (e.g., at 0.38muM for SF-539 [central nervous system], at 0.58muM for HT-29 [colon], at 0.20muM for DMS114 [lung], at 0.21muM for LOX-IMVI [melanoma], and at 0.23muM for MKN74 [stomach]. The binding protein of RID-B that exerts the apoptosis events is currently under investigation.