ethyl 4-bromo-2-morpholino-1,3-thiazole-5-carboxylate | 1359839-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-bromo-2-morpholino-1,3-thiazole-5-carboxylate
• 英文别名: Ethyl 4-bromo-2-morpholin-4-yl-1,3-thiazole-5-carboxylate
• CAS: 1359839-26-1
• 化学式: C₁₀H₁₃BrN₂O₃S
• 分子量: 321.195
• InChiKey: NABJWIFYUPNHHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 1,2-二溴乙烷 、 N,N-二甲基甲酰胺 、 4-氯-3-氟溴苄 、 ethyl 4-bromo-2-morpholino-1,3-thiazole-5-carboxylate 、 在 锌 、 二(三叔丁基膦)钯 氯化铵 、 水 、 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 二氯甲烷 、 EtOAc hexanes 作用下， 反应 17.25h， 以to afford ethyl 4-(4-chloro-3-fluorobenzyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxylate (245 mg, yield 68.2%)的产率得到Ethyl 4-(4-chloro-3-fluorobenzyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  HETEROARYLS AND USES THEREOF

  摘要：

  本发明提供了式IA-i-a或IB-i-a及其子集的化合物:其中Z、HY、R1、R2、R3、G1、W、n和A及其子集如说明书所述。这些化合物是PI3K的抑制剂，因此可用于治疗增殖、炎症或心血管疾病。

  公开号：

  US20120172345A1
• 作为产物：
  描述：

  4-amino-2-(4-morpholinyl)-thiazole-5-carboxylic-ethylester 在 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 以40%的产率得到ethyl 4-bromo-2-morpholino-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  4-Bromo-2-(piperidin-1-yl)thiazol-5-yl-phenyl methanone (12b) inhibits Na+/K+-ATPase and Ras oncogene activity in cancer cells

  摘要：

  The in vitro growth inhibitory activity of 26 thiazoles (including 4-halogeno-2,5-disubtituted-1,3-thiazoles) and 5 thienothiazoles was assessed on a panel of 6 human cancer cell lines, including glioma cell lines. (4-Chloro-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12a) and (4-bromo-2-(piperidin-1-yl)thiazol-5-yl)(phenyl)methanone (12b) displayed similar to 10 times greater in vitro growth inhibitory activity than perillyl alcohol (POH), which therapeutically benefits glioma patients through the inhibition of both alpha-1 Na+/K+-ATPase (NAK) and Ras oncogene activity. The in vitro cytostatic activities (as revealed by quantitative videomicroscopy) displayed by 12a and 12b were independent of the intrinsic resistance to pro-apoptotic stimuli associated with cancer cells. Compounds 12a and 12b displayed relatively similar inhibitory activities on purified guinea pig brain preparations that mainly express NAK alpha-2 and alpha-3 subunits, whereas only compound 12b was efficacious against purified guinea pig kidney preparations that mainly express the NAK alpha-1 subunit, which is also expressed in gliomas, melanomas and non-small-cell lung cancers NSCLCs. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.046

文献信息

• Heteroaryls and uses thereof
  申请人：Freeze Brian S.

  公开号：US08796268B2

  公开（公告）日：2014-08-05

  This invention provides compounds of formula IA-i-a or IB-i-a and subsets thereof: wherein Z, HY, R1, R2, R3, G1, W, n, and A and subsets thereof are as described in the specification. The compounds are inhibitors of PI3K and are thus useful for treating proliferative, inflammatory, or cardiovascular disorders.

  本发明提供了公式IA-i-a或IB-i-a及其子集的化合物：其中Z，HY，R1，R2，R3，G1，W，n和A以及其子集如规范中所述。这些化合物是PI3K的抑制剂，因此可用于治疗增殖性，炎症性或心血管疾病。
• US8765746B2
  申请人：——

  公开号：US8765746B2

  公开（公告）日：2014-07-01
• US8796268B2
  申请人：——

  公开号：US8796268B2

  公开（公告）日：2014-08-05
• US8796271B2
  申请人：——

  公开号：US8796271B2

  公开（公告）日：2014-08-05
• [EN] HETEROARYLS AND USES THEREOF<br/>[FR] HÉTÉROARYLES ET LEURS UTILISATIONS
  申请人：MILLENNIUM PHARM INC

  公开号：WO2012021696A1

  公开（公告）日：2012-02-16

  This invention provides compounds of formula (IA-a) or (IB-a) and subsets thereof: wherein Z, HY, R1, R2, G1 W, n, and A and subsets thereof are as described in the specification. The compounds are inhibitors of PI3K and are thus useful for treating proliferative, inflammatory, or cardiovascular disorders.