2-Methyl-4-benzyliden-4H-3,1-benzoxazine | 622379-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-Methyl-4-benzyliden-4H-3,1-benzoxazine
• 英文别名: 4-benzylidene-2-methyl-3,1-benzoxazine
• CAS: 622379-26-4
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: BOWWAWZYQWXPMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-碘苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 、 三叔丁基膦[双（三氟甲基）磺酰亚胺基]金（I） 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-Methyl-4-benzyliden-4H-3,1-benzoxazine
  参考文献：
  名称：

  Differential Effect of 4H-Benzo[d] [1, 3]oxazines on the Proliferation of Breast Cancer Cell Lines

  摘要：

  Background: A family of 4H-benzo[d][1,3]oxazines were obtained from a group of N-(2-alkynyl)aryl benzamides precursors via gold(I) catalysed chemoselective 6-exo-dig C-O cyclization. Method: The precursors and oxazines obtained were studied in breast cancer cell lines MCF-7, CAMA-1, HCC1954 and SKBR-3 with differential biological activity showing various degrees of inhibition with a notable effect for those that had an aryl substituted at C-2 of the molecules. 4H-benzo[d][1,3]oxazines showed an IC50 rating from 0.30 to 157.4 µM in MCF-7, 0.16 to 139 in CAMA-1, 0.09 to 93.08 in SKBR-3, and 0.51 to 157.2 in HCC1954 cells. Results: We observed that etoposide is similar to benzoxazines while taxol effect is more potent. Four cell lines responded to benzoxazines while SKBR-3 cell line responded to precursors and benzoxazines. Compounds 16, 24, 25 and 26 have the potent effect in cell proliferation inhibition in the 4 cell lines tested and correlated with oxidant activity suggesting a possible mechanism by ROS generation. Conclusion: These compounds represent possible drug candidates for the treatment of breast cancer. However, further trials are needed to elucidate its full effect on cellular and molecular features of cancer.

  DOI：

  10.2174/0109298673292365240422104456

文献信息

• 2-Aryl and 2-Heteroaryl Indoles from 1-Alkynes and <i>o</i>-Iodotrifluoroacetanilide through a Domino Copper-Catalyzed Coupling−Cyclization Process
  作者：Sandro Cacchi、Giancarlo Fabrizi、Luca M. Parisi

  DOI：10.1021/ol035378r

  日期：2003.10.1

  [GRAPHICS]A general method for the synthesis of 2-aryl and 2-heteroaryl indoles from aryl iodides and 1-alkynes through a domino copper-catalyzed process is reported. The best results have been obtained with [Cu(phen)(PPh3)(2)]NO3 in the presence of K3PO4 in toluene or dioxane at 110 degreesC. 2-Aryl and 2-heteroaryl indoles can also be isolated in good yields by using catalysts derived from CuI and PPh3 in dioxane at 110 degreesC.