N-(6-methyl-1,3-benzothiazol-2-yl)-2-({4-oxo-3-phenyl-3H,4H,6H,7H-thieno[3,2-d]pyrimidin-2-yl}sulfanyl)acetamide

• ChemBase编号: 154356
• 分子式: C22H18N4O2S3
• 平均质量: 466.59892
• 单一同位素质量: 466.05918884
• SMILES: Cc1ccc2c(c1)sc(n2)NC(=O)CSc1nc2c(c(=O)n1c1ccccc1)SCC2
• Canonical SMILES: O=C(Nc1nc2c(s1)cc(cc2)C)CSc1nc2CCSc2c(=O)n1c1ccccc1
• InChI: InChI=1S/C22H18N4O2S3/c1-13-7-8-15-17(11-13)31-21(23-15)25-18(27)12-30-22-24-16-9-10-29-19(16)20(28)26(22)14-5-3-2-4-6-14/h2-8,11H,9-10,12H2,1H3,(H,23,25,27)
• InChIKey: WRKPZSMRWPJJDH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-(6-methyl-1,3-benzothiazol-2-yl)-2-({4-oxo-3-phenyl-3H,4H,6H,7H-thieno[3,2-d]pyrimidin-2-yl}sulfanyl)acetamide
• IUPAC传统名: N-(6-methyl-1,3-benzothiazol-2-yl)-2-({4-oxo-3-phenyl-6H,7H-thieno[3,2-d]pyrimidin-2-yl}sulfanyl)acetamide
• 别名: N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-acetamide; IWP-2; N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]acetamide; IWP-2

登记号

• CAS号: 686770-61-6
• MDL号: MFCD04457599
• PubChem SID: 162248495
• PubChem CID: 2155128

理论计算性质

• Acid pKa: 10.617733
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 4.968937
• LogD (pH = 7.4): 4.968691
• Log P: 4.9689407
• 摩尔折射率: 128.7995 cm^3
• 极化性: 49.32451 Å^3
• 极化表面积: 74.66 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >5 mg/mL
• 外观: powder

安全信息

• 保存条件: desiccated
• 德国WGK号: 2
• 保存温度: room temp

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H18N4O2S3

详细说明

Sigma Aldrich - I0536

Biochem/physiol Actions
IWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. Wnt/b-catenin (‘canonical’) pathway maintains transcriptional programs that enable stem cells to remain multipotent. Hyperactivation of the Wnt/b-catenin pathway leads to disease stage. IWP-2 inhibits Wnt production. It appears that IWP inactivates Porcn function either by directly inhibiting the Porcn active site or by modulating the function of a Porcn regulator. Porcn is a member of the membrane-bound O-acyltransferase (MBOAT) family, which adds a palmitoyl group to Wnt proteins that is essential to their signaling ability and is required for Wnt secretion. IWP-2 is useful in both regenerative medicine and anticancer efforts.

Toronto Research Chemicals - I941600

IWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. IWP-2 is useful in the treatment diseases and conditions such as cancer, degenerative diseases, type II diabetes and osteopetrosis.

参考文献

• Poss, K., et al.: Dev. Biol., 222, 347 (2000)
• Tanaka, K., et al.: Eur. J. Biochem., 267, 4300 (2000)
• Clevers, H., et al.: Cell, 2006, 127, 469 (2000)