5-{[4-(ethylsulfanyl)phenyl]methylidene}imidazolidine-2,4-dione

• ChemBase编号: 154505
• 分子式: C12H12N2O2S
• 平均质量: 248.30088
• 单一同位素质量: 248.06194863
• SMILES: CCSc1ccc(cc1)/C=C/1\C(=O)NC(=O)N1
• Canonical SMILES: CCSc1ccc(cc1)/C=C\1/NC(=O)NC1=O
• InChI: InChI=1S/C12H12N2O2S/c1-2-17-9-5-3-8(4-6-9)7-10-11(15)14-12(16)13-10/h3-7H,2H2,1H3,(H2,13,14,15,16)
• InChIKey: UWMDBDYLNJITCD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-{[4-(ethylsulfanyl)phenyl]methylidene}imidazolidine-2,4-dione
• IUPAC传统名: 5-{[4-(ethylsulfanyl)phenyl]methylidene}imidazolidine-2,4-dione
• 别名: (Z)-5-(4-(ethylthio)benzylidene)-hydantoin; (Z)-5-[4-(Ethylthio)benzylidene]imidazolidine-2,4-dione; 5-(4-Ethylsulfanylbenzylidene)imidazolidine-2,4-dione; S-PMH

登记号

• MDL号: MFCD12912441
• PubChem SID: 162248644
• PubChem CID: 71311882

理论计算性质

• Acid pKa: 8.229958
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 1.5579511
• LogD (pH = 7.4): 1.4995682
• Log P: 1.5587499
• 摩尔折射率: 69.2842 cm^3
• 极化性: 25.942923 Å^3
• 极化表面积: 58.2 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >20 mg/mL
• 外观: yellow powder

安全信息

• 德国WGK号: 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C12H12N2O2S

详细说明

Sigma Aldrich - S0826

Biochem/physiol Actions
S-PMH augments cell-cell adhesion by enhancing tight and adherens junctions (TJ and AJ) and by abolishing the destabilizing actions of Calcitonin (CT) on these complexes. Calcitonin and its receptor are expressed in prostate cell cancers and plays a pivotal role in metastasis and tumorgenesis. It appears that CT promotes prostate cancer metastasis by reducing cell-cell adhesion through the disassembly of tight and adherens junctions and activation of B-catenin signaling. S-PMH apparently blocks CT-stimulated alphavbeta3 activity (a key factor in bone metastasis). In a nude mice model I.p. administered S-PMH and its S-ethyl derivative decreased orthotopic tumor growth and inhibited the formation of tumor micrometastases in distant organs. S-PMH is relatively nontoxic in a cell proliferation assay.