(9ci)-2-[(乙基硫代)甲基]-1H-苯并咪唑 | 99069-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9ci)-2-[(乙基硫代)甲基]-1H-苯并咪唑
• 英文名称: (ethylthiomethyl)benzimidazole
• 英文别名: 2-[(methylmethylsulfanyl)methyl]-1H-benzimidazole；2-(ethylmercapto-methyl)-1H-benzimidazole；2-(Aethylmercapto-methyl)-1H-benzimidazol；2-((Ethylthio)methyl)-1H-benzo[d]imidazole；2-(ethylsulfanylmethyl)-1H-benzimidazole
• CAS: 99069-37-1
• 化学式: C₁₀H₁₂N₂S
• mdl: MFCD00159959
• 分子量: 192.285
• InChiKey: CHHFCKAWSWMMIW-UHFFFAOYSA-N

物化性质

• 密度：
  1.213

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (9ci)-2-[(乙基硫代)甲基]-1H-苯并咪唑 在 sodium periodate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-2-[(methylsulfinyl)methyl]-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Analogues of the Pan Class I Phosphatidylinositol 3-Kinase (PI3K) Inhibitor 2-(Difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474)

  摘要：

  A structure activity relationship (SAR) study of the pan class I PI 3-kinase inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474) identified substitution at the 4 and 6 positions of the benzimidazole ring as having significant effects on the potency of substituted derivatives. The 6-amino-4-methoxy analogue displayed a greater than 1000-fold potency enhancement over the corresponding 6-aza-4-methoxy analogue against all three class Ia PI 3-kinase enzymes (p110 alpha, p110 beta, and p110 delta) and also displayed significant potency against two mutant forms of the p110 alpha isoform (H1047R and E545K). This compound was also evaluated in vivo against a U87MG human glioblastoma tumor xenograft model in Ragl(-/-) mice, and at a dose of 50 mg/kg given by ip injection at a qd x 10 dosing schedule it dramatically reduced cancer growth by 81% compared to untreated controls.

  DOI：

  10.1021/jm200688y
• 作为产物：
  描述：

  2-巯基甲基苯并咪唑 、 sodium ethanolate 在 溴乙烷 作用下， 生成 (9ci)-2-[(乙基硫代)甲基]-1H-苯并咪唑
  参考文献：
  名称：

  Studies on the Antitubercular Compounds. XIII. Preparation of Some Derivatives of Benzimidazole and 2,1,3-Benzothiadiazole

  摘要：

  DOI：

  10.1246/bcsj.31.252

文献信息

• Shi Juen; Le Xueyi; Chen Liaorong, Inorganica Chimica Acta, 1988, vol. 153, p. 5 - 8
  作者：Shi Juen、Le Xueyi、Chen Liaorong、Luo Baoshen

  DOI：——

  日期：——
• Studies on the Antitubercular Compounds. XIII. Preparation of Some Derivatives of Benzimidazole and 2,1,3-Benzothiadiazole
  作者：Isao Sekikawa

  DOI：10.1246/bcsj.31.252

  日期：1958.3
• Synthesis and Biological Evaluation of Novel Analogues of the Pan Class I Phosphatidylinositol 3-Kinase (PI3K) Inhibitor 2-(Difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1<i>H</i>-benzimidazole (ZSTK474)
  作者：Gordon W. Rewcastle、Swarna A. Gamage、Jack U. Flanagan、Raphael Frederick、William A. Denny、Bruce C. Baguley、Philip Kestell、Ripudaman Singh、Jackie D. Kendall、Elaine S. Marshall、Claire L. Lill、Woo-Jeong Lee、Sharada Kolekar、Christina M. Buchanan、Stephen M. F. Jamieson、Peter R. Shepherd

  DOI：10.1021/jm200688y

  日期：2011.10.27

  A structure activity relationship (SAR) study of the pan class I PI 3-kinase inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474) identified substitution at the 4 and 6 positions of the benzimidazole ring as having significant effects on the potency of substituted derivatives. The 6-amino-4-methoxy analogue displayed a greater than 1000-fold potency enhancement over the corresponding 6-aza-4-methoxy analogue against all three class Ia PI 3-kinase enzymes (p110 alpha, p110 beta, and p110 delta) and also displayed significant potency against two mutant forms of the p110 alpha isoform (H1047R and E545K). This compound was also evaluated in vivo against a U87MG human glioblastoma tumor xenograft model in Ragl(-/-) mice, and at a dose of 50 mg/kg given by ip injection at a qd x 10 dosing schedule it dramatically reduced cancer growth by 81% compared to untreated controls.