3-amino-8-bromo-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile | 432026-29-4

• 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-(4-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
• CAS: 432026-29-4
• 化学式: C₂₀H₁₂BrClN₂O
• 分子量: 411.685
• InChiKey: DBPNWFPNSKAGHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-8-bromo-1-(4-chlorophenyl)-1H-benzo[f]chromene-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-chlorophenyl)-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：

  4-氯苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 3-amino-8-bromo-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
  参考文献：
  名称：

  Synthesis and DFT Study of 7-Bromophenylnaphthopyran Moieties

  摘要：

  在乙醇/哌啶回流条件下，对 6-溴-2-萘酚（1）、对氯苯甲醛（2）和丙二腈或氰乙酸乙酯（3）进行了单锅三组分反应，生成了 6-溴-2-萘酚和对氯苯甲醛。 丙二腈或氰乙酸乙酯（3）在乙醇/哌啶中的三组分反应，在回流条件下生成 4H-萘并[2,1-b]吡喃-3-甲腈（4a）和 4H-萘并[2,1-b]吡喃-3-甲酸乙酯（4b）衍生物。 衍生物。利用红外光谱、1H NMR、13C 核磁共振、质谱和紫外可见光谱测定了这些化合物的结构。化合物 4a 和 4b 的分子几何形状是在 B3LYP/6GP 下确定的。 在 B3LYP/631+G(d) 水平上确定。对两种同系物和两种构象进行了几何优化。 和两种构象进行了几何优化。同分异构体之间的差异约为 7.942 kcal/mol，而旋转构象体之间的差异仅为 0.511 kcal/mol。 仅相差 0.511 kcal/mol。全局亲电性、硬度、软度和局部 计算出了全局亲电性、硬度、软度和局部凝聚福井函数，并将其视为分子反应性描述符，此外还计算了 还计算了前沿分子轨道（HOMO 和 LUMO）。

  DOI：

  10.14233/ajchem.2023.28032

文献信息

• A proficient microwave synthesis with structure elucidation and the exploitation of the biological behavior of the newly halogenated 3-amino-1H-benzo[f]chromene molecules, targeting dual inhibition of topoisomerase II and microtubules
  作者：Ahmed M. Fouda、Rawda M. Okasha、Fawzia F. Alblewi、Ahmed Mora、Tarek H Afifi、Ahmed M. El-Agrody

  DOI：10.1016/j.bioorg.2019.103549

  日期：2020.1

  Caspase production, and the DNA fragmentation. This study also revealed that the desired compounds stimulate cell cycle arrest at the G2/M phases, increase the production of Caspases 3, 8, and 9, and finally cause intrinsic and extrinsic apoptotic cell death. Moreover, these compounds suppress the action of the topoisomerase II enzyme and also disrupt the microtubule functions. The SAR study of the

  为了开发具有抗增殖活性的新型强效试剂，在微波辐射条件下设计并合成了一系列与8-溴-1H-苯并[f]亚甲基部分（4a-m）连接的β-乙腈。根据目标化合物的光谱数据确定其结构：IR，1 H NMR，13 C NMR，13 C NMR-DEPT / APT，19 F NMR和MS。此外，采用生存力测定法，与阳性对照长春碱和阿霉素相比，评估了针对人类癌细胞系MCF-7，HCT-116和HepG-2的抗增殖特性。获得的结果证实，大多数测试分子​​显示出对三种癌细胞的强而有选择性的细胞毒活性。最有效的细胞毒性化合物4b，4d，4e，4i，选择4k和4k进行进一步检查，例如细胞周期分析，细胞凋亡测定，Caspase产生和DNA片段化。该研究还揭示了所需化合物刺激了细胞周期在G2 / M期的停滞，增加了Caspases 3、8和9的产生，并最终导致内在和外在的凋亡细胞死亡。而且，这些化合物抑制拓扑异构酶I
• 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.
• Synthesis and antimicrobial activities of novel naphtho[2,1-b]pyran, pyrano[2,3-d]pyrimidine and pyrano[3,2-e][1,2,4]triazolo[2,3-c]-pyrimidine derivatives
  作者：Ahmed H Bedair、Hussien A Emam、Nagwa A El-Hady、Kamal A.R Ahmed、Ahmed M El-Agrody

  DOI：10.1016/s0014-827x(01)01168-5

  日期：2001.12

  The synthesis of new naphtho[1',2':5,6]pyrano[2,3-d]pyrimidines and related heterocycles has been reported. The key intermediate 3-amino-8-bromo-1-(p-methoxyphenyl)-1H-naphtho[2,1-b] pyran-2-carbonitrile (3c) was obtained in one pot synthesis by treating alpha-cyanocinnamonitrile (1c) with 6-bromo-2-naphthol (2). Antimicrobial activity was shown for some of the synthesized compounds.

  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。
• Synthesis and DFT Study of 7-Bromophenylnaphthopyran Moieties
  作者：Ashraf Hassan Fekry Abd El-Wahab、Hany Mostafa Mohamed

  DOI：10.14233/ajchem.2023.28032

  日期：——

  A one-pot, three-component reaction of 6-bromo-2-naphthol (1), p-chlorobenzaldehyde (2) and malononitrile or ethyl cyanoacetate (3) in ethanol/piperidine under reflux was performed to afford 4H-naphtho[2,1-b]pyrano-3-carbonitrile (4a) and ethyl 4H-naphtho[2,1-b]pyrano-3-carboxylate (4b) derivatives, respectively. The structure of these compounds was determined using IR, 1H NMR, 13C NMR, mass spectroscopy and UV-Vis spectra. The molecular geometry of compounds 4a and 4b was determined at the B3LYP/631+G(d) level. The geometric optimization was performed on two tautomers and two conformers. Tautomers were separated by about 7.942 kcal/mol, while rotational conformers were separated by just 0.511 kcal/mol. The global electrophilicity, hardness, softness and local condensed Fukui functions were calculated and considered as molecular reactivity descriptors, moreover the frontier molecular orbitals (HOMO and LUMO) were also calculated.

  在乙醇/哌啶回流条件下，对 6-溴-2-萘酚（1）、对氯苯甲醛（2）和丙二腈或氰乙酸乙酯（3）进行了单锅三组分反应，生成了 6-溴-2-萘酚和对氯苯甲醛。 丙二腈或氰乙酸乙酯（3）在乙醇/哌啶中的三组分反应，在回流条件下生成 4H-萘并[2,1-b]吡喃-3-甲腈（4a）和 4H-萘并[2,1-b]吡喃-3-甲酸乙酯（4b）衍生物。 衍生物。利用红外光谱、1H NMR、13C 核磁共振、质谱和紫外可见光谱测定了这些化合物的结构。化合物 4a 和 4b 的分子几何形状是在 B3LYP/6GP 下确定的。 在 B3LYP/631+G(d) 水平上确定。对两种同系物和两种构象进行了几何优化。 和两种构象进行了几何优化。同分异构体之间的差异约为 7.942 kcal/mol，而旋转构象体之间的差异仅为 0.511 kcal/mol。 仅相差 0.511 kcal/mol。全局亲电性、硬度、软度和局部 计算出了全局亲电性、硬度、软度和局部凝聚福井函数，并将其视为分子反应性描述符，此外还计算了 还计算了前沿分子轨道（HOMO 和 LUMO）。