4-(4-phenylbutoxy)-7H-furo[3,2-g]chromen-7-one

• ChemBase编号: 155006
• 分子式: C21H18O4
• 平均质量: 334.36522
• 单一同位素质量: 334.12050906
• SMILES: c1ccc(cc1)CCCCOc1c2ccc(=O)oc2cc2c1cco2
• Canonical SMILES: O=c1ccc2c(o1)cc1c(c2OCCCCc2ccccc2)cco1
• InChI: InChI=1S/C21H18O4/c22-20-10-9-16-19(25-20)14-18-17(11-13-23-18)21(16)24-12-5-4-8-15-6-2-1-3-7-15/h1-3,6-7,9-11,13-14H,4-5,8,12H2
• InChIKey: JJAWGNIQEOFURP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-(4-phenylbutoxy)-7H-furo[3,2-g]chromen-7-one
• IUPAC传统名: 4-(4-phenylbutoxy)furo[3,2-g]chromen-7-one
• 别名: 5-(4-Phenylbutoxy)psoralen; Psora-4; 4-(4-Phenylbutoxy)-7H-furo[3,2-g][1]benzopyran-7-one; Psora 4

登记号

• CAS号: 724709-68-6
• PubChem SID: 162249144; 24278012
• PubChem CID: 6603977

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 4.6870832
• LogD (pH = 7.4): 4.6870832
• Log P: 4.6870832
• 摩尔折射率: 95.4225 cm^3
• 极化性: 37.64698 Å^3
• 极化表面积: 48.67 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ~16 mg/mL; H2O: insoluble
• 外观: off-white solid

安全信息

• 保存条件: protect from light; under inert gas
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335-H413
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H18O4

详细说明

Sigma Aldrich - P9872

Biochem/physiol Actions
The lymphocyte potassium channel Kv1.3 is regarded as a new target for immunosuppression. Psora-4 is the most potent small-molecule Kv1.3 blocker known. It blocked Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC50 value of 3 nM, by preferentially binding to the C-type inactivated state of the channel. It exhibited 17- to 70-fold selectivity for Kv1.3 over closely related Kv1-family channels (Kv1.1, Kv1.2, Kv1.4, and Kv1.7) with the exception of Kv1.5 (EC50, 7.7 nM) and showed no effect on human ether-a-go-go-related channel, Kv3.1, the calcium-activated K+ channels (IKCa1, SK1-SK3, and BKCa), or the neuronal NaV1.2 channel. In a test of in vivo toxicity in rats, Psora-4 did not display any signs of acute toxicity after five daily subcutaneous injections at 33 mg/kg body weight. Psora-4 selectively suppressed the proliferation of human and rat myelin-specific effector memory T cells with EC50 values of 25 and 60 nM, respectively, without persistently suppressing peripheral blood naive and central memory T cells. Because autoantigen-specific effector memory T cells contribute to the pathogenesis of T cell-mediated autoimmune diseases such as multiple sclerosis, Psora-4 and other Kv1.3 blockers may be useful as immunomodulators for the therapy of autoimmune disord.

Toronto Research Chemicals - P839700

Psora-4 is the most potent small-molecule Kv1.3 blocker known. Psora-4 and other Kv1.3 blockers may be useful as immunomodulators for the therapy of autoimmune disorders.

参考文献

• Vennekamp, et al.: Mol. Pharmacol. 65 1364 (2004)
• Schmitz, et al.: Mol. Pharmacol., 68, 1254 (2004)
• Li, et al.: Am. J. Physiol. Cell Physiol., 290, 345 (2004)