1-(2-chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one

• ChemBase编号: 153855
• 分子式: C15H12ClF3N4O
• 平均质量: 356.7301896
• 单一同位素质量: 356.06517336
• SMILES: C[C@H](Cc1[nH]c(=O)c2cnn(c2n1)c1ccccc1Cl)C(F)(F)F
• Canonical SMILES: C[C@@H](C(F)(F)F)Cc1[nH]c(=O)c2c(n1)n(nc2)c1ccccc1Cl
• InChI: InChI=1S/C15H12ClF3N4O/c1-8(15(17,18)19)6-12-21-13-9(14(24)22-12)7-20-23(13)11-5-3-2-4-10(11)16/h2-5,7-8H,6H2,1H3,(H,21,22,24)/t8-/m1/s1
• InChIKey: FFPXPXOAFQCNBS-MRVPVSSYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(2-chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one
• IUPAC传统名: 1-(2-chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one
• 别名: 1-(2-Chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-one; BAY 73-6691

登记号

• CAS号: 794568-92-6
• MDL号: MFCD08705319
• PubChem SID: 24724419; 162247994
• PubChem CID: 16078952

理论计算性质

• Acid pKa: 9.204311
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.2619364
• LogD (pH = 7.4): 3.256027
• Log P: 3.2620127
• 摩尔折射率: 84.4441 cm^3
• 极化性: 30.715345 Å^3
• 极化表面积: 59.28 Å^2
• 可自由旋转的化学键: 4
• 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: off-white powder

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25-36/37/38
• 安全公开号: 26-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H315-H319-H335-H413
• GHS警示性声明: P261-P264-P301 + P310-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H12ClF3N4O

详细说明

Sigma Aldrich - B3561

Biochem/physiol Actions
BAY 73-6691 was characterized in vitro as the first potent and selective inhibitor of phosphodiesterase 9 (PDE9), which is currently under preclinical development for the treatment of Alzheimer′s disease. This compound selectively inhibits human (IC50 = 55 nM) and murine (IC50 = 100 nM) PDE9 activity in vitro and shows only moderate activity against other cyclic nucleotide-specific phosphodiesterases. BAY 73-6691 alone did not significantly increase basal cGMP levels. The PDE9 inhibitor significantly potentiated the cGMP signals generated by sGC activating compounds such as BAY 58-2667 or 5-cyclopropyl-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-ylamine (BAY 41-2272) and induced leftward shifts of the corresponding concentration-response curves. The newly generated PDE9 reporter cell line show that BAY 73-6691 is able to efficiently penetrate cells and to inhibit intracellular PDE9 activity.†