4-methoxy-N-(2-(phenylethynyl)phenyl)benzamide | 1321594-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-N-(2-(phenylethynyl)phenyl)benzamide
• CAS: 1321594-85-7
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: WWCANWXMUJZRNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(2-(phenylethynyl)phenyl)benzamide 在 (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） 作用下， 以 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 4-methoxy-N-(2-(phenylethynyl)phenyl)benzamide
  参考文献：
  名称：

  铜催化的2-乙腈的氧化环封闭和碳芳基化

  摘要：

  开发了一种新的铜催化的乙炔基苯胺与二芳基碘鎓盐的氧化性闭环反应，用于具有完全取代的exo双键的苯并恶嗪的高度模块化结构。氧化转化包括一个不寻常的6- exo - dig环化步骤，形成C–O和C–C键。

  DOI：

  10.1021/ol402600r

文献信息

• Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines
  作者：Zhong-Jian Cai、Chao Yang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c5cc06510k

  日期：——

  A Pd-catalyzed highly regioselective 6-exo-dig cyclization/alkenylation reaction of ortho-ethynylanilides has been developed.

  一种钯催化的高区域选择性6-exo-dig环化/烯基化反应已经被开发出来，用于ortho-乙炔基苯胺。
• Synthesis of 3,1-Benzothiazines from 2-Alkenyl- and 2-Alkynylanilides and Lawesson Reagent
  作者：Kentaro Okuma、Saori Ozaki、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.3987/com-11-12180

  日期：——

  Reaction of 2-vinylacetanilide with P4S10 gave 2-vinylthioacetanilide, whereas reaction of 2-vinylacetanilide with Lawesson reagent (LR) afforded 2,4-dimethyl-4H-3,1-benzothiazine in 62% yield. Reaction of 2-alkynylanilides with LR gave 4-exomethylene-4H-3,1-benzothiazines in good yields.