2-[(3S)-2,6-dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase编号: 133283
• 分子式: C13H10N2O4
• 平均质量: 258.2295
• 单一同位素质量: 258.06405681
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)[C@H]1CCC(=O)NC1=O
• Canonical SMILES: O=C1CC[C@@H](C(=O)N1)N1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m0/s1
• InChIKey: UEJJHQNACJXSKW-VIFPVBQESA-N

名称和登记号

名称

• IUPAC标准名: 2-[(3S)-2,6-dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC传统名: (+)-thalidomide
• 别名: S(-)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione; (-)-Thalidomide; (S)-(-)-2-(2,6-Dioxo-3-piperidinyl)-1H-iso-indole-1,3(2H)-dione; (S)-Thalidomide; NSC 91730; (S)-(-)-Thalidomide

登记号

• CAS号: 841-67-8
• MDL号: MFCD00210219
• PubChem SID: 24899969; 162227560
• PubChem CID: 92142

理论计算性质

• Acid pKa: 11.593279
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 0.01570701
• LogD (pH = 7.4): 0.015679834
• Log P: 0.015707357
• 摩尔折射率: 64.3248 cm^3
• 极化性: 24.014824 Å^3
• 极化表面积: 83.55 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Butyl Acetate; DMSO: soluble; Ethanol; ethanol: insoluble; Ethyl Acetate; H2O: insoluble; Methanol; Sparingly soluble in Water
• 外观: white solid; White Solid
• 熔点: 269-271°C
• 比旋光度: [α]23/D -62.6°, c = 2 in DMF(lit.)

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: TI4925050
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 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): 2
• 危险公开号: 61-22
• 安全公开号: 53-36/37/39-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H360
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

药理学性质

• 相关基因信息: human ... LITAF(9516), TNF(7124)mouse ... Nos2(18126)rat ... Nos1(24598)

产品相关信息

• 纯度: >98%

详细说明

Sigma Aldrich - T150

Biochem/physiol Actions
(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α); inhibitor of angiogenesis. (S)-Thalidomide is a teratogenic enatiomer.

Toronto Research Chemicals - T338860

Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative.

参考文献

• D’Amato, r.J., et al.: Proc. Natl. Acad. Sci. USA, 91, 4082 (1994)
• Makonkawkeyoon, S., et al.: Proc. Natl. Acad. Sci. USA, 90, 5974 (1994)
• Schumacher, H., et al.: J. Pharmacol. Exp. Therap., 160, 189 (1968)