3-amino-8-bromo-1-(p-methoxyphenyl)-1H-naphtho[2,1-b]pyran-2-carbonitrile | 432026-30-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-amino-8-bromo-1-(p-methoxyphenyl)-1H-naphtho[2,1-b]pyran-2-carbonitrile
• 英文别名: 3-amino-8-bromo-1-(4-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrile
• CAS: 432026-30-7
• 化学式: C₂₁H₁₅BrN₂O₂
• 分子量: 407.266
• InChiKey: QEDWMWNSDXIGMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-8-bromo-1-(p-methoxyphenyl)-1H-naphtho[2,1-b]pyran-2-carbonitrile 在 乙酸酐 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.75h， 生成 10-amino-3-bromo-12-(p-methoxyphenyl)-11-imino-10,11-dihydro-12H-naphtho[1',2':5,6]pyrano[2,3-d]pyrimidine
  参考文献：
  名称：

  新型萘并[2,1-b]吡喃，吡喃并[2,3-d]嘧啶和吡喃并[3,2-e] [1,2,4]三唑并[2,3-c]-的合成及抑菌活性嘧啶衍生物。

  摘要：

  已经报道了新的萘并[1'，2'：5,6]吡喃并[2,3-d]嘧啶和相关杂环的合成。通过处理α-氰基肉桂腈（1c）一次合成即可获得关键的中间体3-氨基-8-溴-1-（对甲氧基苯基）-1H-萘并[2,1-b]吡喃-2-腈（3c） ）和6-溴-2-萘酚（2）。对某些合成化合物显示了抗菌活性。

  DOI：

  10.1016/s0014-827x(01)01168-5
• 作为产物：
  描述：

  6-溴-2-萘酚 、 (4-甲氧基苄烯)丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以91%的产率得到3-amino-8-bromo-1-(p-methoxyphenyl)-1H-naphtho[2,1-b]pyran-2-carbonitrile
  参考文献：
  名称：

  新型萘并[2,1-b]吡喃，吡喃并[2,3-d]嘧啶和吡喃并[3,2-e] [1,2,4]三唑并[2,3-c]-的合成及抑菌活性嘧啶衍生物。

  摘要：

  已经报道了新的萘并[1'，2'：5,6]吡喃并[2,3-d]嘧啶和相关杂环的合成。通过处理α-氰基肉桂腈（1c）一次合成即可获得关键的中间体3-氨基-8-溴-1-（对甲氧基苯基）-1H-萘并[2,1-b]吡喃-2-腈（3c） ）和6-溴-2-萘酚（2）。对某些合成化合物显示了抗菌活性。

  DOI：

  10.1016/s0014-827x(01)01168-5

文献信息

• Introducing novel potent anticancer agents of<i>1H</i>-benzo[<i>f</i>]chromene scaffolds, targeting<i>c-Src</i>kinase enzyme with MDA-MB-231 cell line anti-invasion effect
  作者：Hany E. A. Ahmed、Mohammed A. A. El-Nassag、Ahmed H. Hassan、Rawda M. Okasha、Saleh Ihmaid、Ahmed M. Fouda、Tarek H. Afifi、Ateyatallah Aljuhani、Ahmed M. El-Agrody

  DOI：10.1080/14756366.2018.1476503

  日期：2018.1.1

  In our effort to develop novel and powerful agents with anti-proliferative activity, two new series of 1H-benzo[f]chromene derivatives, 4a-h and 6a-h, were synthesised using heterocyclocondensation methodologies under microwave irradiation condition. The structures of the target compounds were established on the basis of their spectral data, IR, H-1 NMR, C-13 NMR, C-13 NMR-DEPT/APT, and MS data. The new compounds have been examined for their anti-proliferative activity against three cancer cell lines, MCF-7, HCT-116, and HepG-2. Vinblastine and Doxorubicin have been used as positive controls in the viability assay. The obtained results confirmed that most of the tested molecules revealed strong and selective cytotoxic activity against the three cancer cell lines. Moreover, these molecules exhibited weak cytotoxicity on the HFL-1line, which suggested that they might be ideal anticancer candidates. The SAR study of the new benzochromene compounds verified that the substituents on the phenyl ring of 1H-benzo[f]chromene nucleus, accompanied with the presence of bromine atom or methoxy group at the 8-position, increases the ability of these molecules against the different cell lines. Due to their high anti-proliferative activity, compounds 4c and 6e were selected to be examined their proficiency to inhibit the invasiveness of the highly sensitive and invasive breast cancer cell line, MDA-MB-231. The anti-invasion behaviour of these molecules against the highly sensitive, non-oestrogen, and progesterone MDA-MB-231 cell line gave rise to their decreasing metastatic effect compared to the reference drug. Furthermore, this report explores the apoptotic mechanistic pathway of the cytotoxicity of the target compounds and reveals that most of these compounds enhance the Caspase 3/7 activity that could be considered as potential anticancer agents.