4-甲酰基-N-(4-甲氧基苯基)苯甲酰胺 | 1014690-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲酰基-N-(4-甲氧基苯基)苯甲酰胺
• 英文名称: 4-formyl-N-(4-methoxyphenyl)benzamide
• CAS: 1014690-13-1
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: USTLCTOZSMDNHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异烟肼 、 4-甲酰基-N-(4-甲氧基苯基)苯甲酰胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以84%的产率得到(E)-4-((2-isonicotinoylhydrazono)methyl)-N-(4-methoxyphenyl)benzamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel (E)-N-phenyl-4-(pyridine-acylhydrazone) benzamide derivatives as potential antitumor agents for the treatment of multiple myeloma (MM)

  摘要：

  A series of novel (E)-N-phenyl-4-(pyridine-acylhydrazone) benzamide derivatives were designed, synthesized, and evaluated for their anti-proliferative activity against two different human cancer cell lines and one human normal cell line. Compound 8b had the best anti-proliferative activity (IC50, = 0.12 +/- 0.09 mu M, RPMI8226 cells) than the other compounds. And compound 8b had lower toxicity than imatinib. Flow cytometry analysis showed that compound 8b could arrest the cell cycle at the G0/G1 phase, and induce apoptosis of RPMI8226 cells by promoting mitochondrial ROS release, thereby effectively inhibiting cell proliferation. Our findings provided a promising lead compound 8b for further structural optimization and will be instructive for the discovery of more potent antitumor drugs with high selectivity and low toxicity.

  DOI：

  10.1016/j.bioorg.2020.104189
• 作为产物：
  描述：

  对醛基苯甲酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 生成 4-甲酰基-N-(4-甲氧基苯基)苯甲酰胺
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel (E)-N-phenyl-4-(pyridine-acylhydrazone) benzamide derivatives as potential antitumor agents for the treatment of multiple myeloma (MM)

  摘要：

  A series of novel (E)-N-phenyl-4-(pyridine-acylhydrazone) benzamide derivatives were designed, synthesized, and evaluated for their anti-proliferative activity against two different human cancer cell lines and one human normal cell line. Compound 8b had the best anti-proliferative activity (IC50, = 0.12 +/- 0.09 mu M, RPMI8226 cells) than the other compounds. And compound 8b had lower toxicity than imatinib. Flow cytometry analysis showed that compound 8b could arrest the cell cycle at the G0/G1 phase, and induce apoptosis of RPMI8226 cells by promoting mitochondrial ROS release, thereby effectively inhibiting cell proliferation. Our findings provided a promising lead compound 8b for further structural optimization and will be instructive for the discovery of more potent antitumor drugs with high selectivity and low toxicity.

  DOI：

  10.1016/j.bioorg.2020.104189

文献信息

• Organocatalytic, Enantioselective Reductive Bis-functionalization of Secondary Amides: One-Pot Construction of Chiral 2,2-Disubstituted 3-Iminoindoline
  作者：Zhen Xu、Xiao-Gang Wang、Yong-Hua Wei、Kan-Lei Ji、Jian-Feng Zheng、Jian-Liang Ye、Pei-Qiang Huang

  DOI：10.1021/acs.orglett.9b02862

  日期：2019.9.20

  We report the first catalytic, enantioselective reductive bis-functionalization of common amides, which provides a facile access to a variety of 2,2-disubstituted 3-iminoindolines in good yields and with excellent enantioselectivities. The reaction conditions are quite mild and can be run on a gram scale. In this one-pot reaction, three C-C bonds, one ring, and one nitrogen-containing tetrasubstituted

  我们报告了常见的酰胺的第一个催化，对映选择性还原双官能化，它提供了一种方便的途径，以良好的产率和优异的对映选择性来获得各种2,2-二取代的3-亚氨基二氢吲哚。反应条件是温和的，可以以克为单位进行。在该一锅法反应中，以催化对映选择性的方式产生三个CC键，一个环和一个含氮的四取代碳立体中心。
• Synthesis and HIV-1 Integrase Inhibition of Novel Bis- or Tetra-Coumarin Analogues
  作者：Chih-Chia Chiang、Jean-François Mouscadet、Hou-Jen Tsai、Chi-Tsan Liu、Ling-Yih Hsu

  DOI：10.1248/cpb.55.1740

  日期：——

  Present studies were undertaken on the preparation of synthetic analogues of bis- or tetra-coumarins and their activity against HIV-1 integrase (HIV-1 IN). Among these coumarin analogues, compounds 14, 16 and 18 were found to be potent molecules against HIV-1 IN at IC50 values of 0.96, 0.58, and 0.49 μM, respectively. The results provided a tool for guiding the further design of more potent antiviral agents and for predicting the affinity of related compounds.

  目前的研究主要针对双香豆素或四香豆素的合成类似物及其对HIV-1整合酶（HIV-1 IN）的活性。在这些香豆素类似物中，化合物14、16和18被发现对HIV-1 IN具有较强的活性，其IC50值分别为0.96、0.58和0.49μM。这些结果为进一步设计更有效的抗病毒药物提供了指导，并为预测相关化合物的亲和力提供了工具。
• Synthesis of 1-benzyl-1H-benzimidazoles as galectin-1 mediated anticancer agents
  作者：Nerella Sridhar Goud、S. Mahammad Ghouse、Jatoth Vishnu、D. Komal、Venu Talla、Ravi Alvala、Jakkula Pranay、Janish Kumar、Insaf A. Qureshi、Mallika Alvala

  DOI：10.1016/j.bioorg.2019.103016

  日期：2019.8

  In our pursuit to develop novel non-carbohydrate small molecule Galectin-1 Inhibitors, we have designed a series of 1-benzyl-1H-benzimidazole derivatives and demonstrated their anticancer activity. The compound 6g, 4-(1-benzyl-5-chloro-1H-benzo [d] imidazol-2-yl)-N-(4-hydroxyphenyl) benzamide was found to be most potent with an IC50, of 7.01 +/- 0.20 mu M and arresting MCF-7 cell growth at G2/M phase and S phase. Induction of apoptosis was confirmed by morphological changes like cell shrinkage, blebbing and cell wall deformation, dose dependent increase in the mitochondrial membrane potential (Delta Psi m) and ROS levels. Further, dose dependent decrease in Gal-1 protein levels proves Gal-1 mediated apoptosis by 6g. Molecular docking studies were performed to understand the Gal-1 interaction with compound 6g. In addition, RP-HPLC studies showed 85.44% of 6g binding to Gal-1. Binding affinity studies by fluorescence spectroscopy and Surface Plasmon Resonance (SPR) showed that 6g binds to Gal-1 with binding constant (K-a) of 1.2 x 10(4) M-1 and equilibrium constant K-D value of 5.76 x 10(-4) M respectively.