4-{7-butyl-5H-pyrrolo[2,3-b]pyrazin-6-yl}phenol

• ChemBase编号: 5015
• 分子式: C16H17N3O
• 平均质量: 267.32568
• 单一同位素质量: 267.13716218
• SMILES: Oc1ccc(cc1)c1[nH]c2nccnc2c1CCCC
• Canonical SMILES: CCCCc1c([nH]c2c1nccn2)c1ccc(cc1)O
• InChI: InChI=1S/C16H17N3O/c1-2-3-4-13-14(11-5-7-12(20)8-6-11)19-16-15(13)17-9-10-18-16/h5-10,20H,2-4H2,1H3,(H,18,19)
• InChIKey: PRIGRJPRGZCFAS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-{7-butyl-5H-pyrrolo[2,3-b]pyrazin-6-yl}phenol
• IUPAC传统名: 4-{7-butyl-5H-pyrrolo[2,3-b]pyrazin-6-yl}phenol
• 别名: 6-PHENYL[5H]PYRROLO[2,3-B]PYRAZINE; 7-n-Butyl-6-(4-hydroxyphenyl)[5H]-pyrrolo[2,3-b]pyrazine; RP-107; RP107, 7-n-Butyl-6-(4-hydroxyphenyl)-[5H]pyrrolo[2,3-b]pyrazine; 4-(7-Butyl-5H-pyrrolo[2,3-b]pyrazin-6-yl)phenol; Aloisine A RP107

登记号

• CAS号: 496864-16-5; 496864-15-4
• MDL号: MFCD04973541
• PubChem SID: 99443835; 160968447
• PubChem CID: 5326843

理论计算性质

JChem

• Acid pKa: 10.033805
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.4999528
• LogD (pH = 7.4): 3.4997516
• Log P: 3.500764
• 摩尔折射率: 78.2501 cm^3
• 极化性: 31.966587 Å^3
• 极化表面积: 61.8 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.35
• LOG S: -3.87
• 溶解度: 3.61e-02 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: >10 mg/mL; H2O: insoluble; Methanol
• 外观: solid; Yellow solid
• 熔点: 281-283°C

安全信息

• 保存条件: -20°C Freezer; desiccated
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26-36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-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): C16H17N3O

详细说明

DrugBank - DB07364

Drug information: experimental

Sigma Aldrich - R3405

Biochem/physiol Actions
RP107 is an activator of cystic fibrosis transmembrane conductance regulator (CFTR) channel. RP107 stimulates wild-type CFTR and mutated CFTR with submicromolar affinity by a cAMP-independent mechanism. EC50 = 89 nM at activating CFTR-dependent C-secretion, an effect inhibited by CFTR(inh)-172 and glibenclaminde. RP107 constitutes a new example of a scaffold structure for the selective activation of CFTR receptors.

Toronto Research Chemicals - A575450

A cell-permeable pyrrolo-pyrazine compound that acts as a potent, selective, reversible, and ATP-competitive inhibitor of cyclin dependent kinases (Cdks: IC50 =150nM, 120 nM, 400 nM and 200 nM for Cdk1/cyclin B, Cdk2/cyclin A, Cdk2/cyclin E, and Cdk5/p25,

参考文献

• Mattey, Y., et al.: J. Med. Chem., 46, 222 (2003)
• Noel, S., et al.: J. Pharmacol. Exp. Ther., 319, 349 (2003)
• Mitsuhashi, M., et al.: Pharm. Res., 25, 1116 (2003)