4-formyl-N-(4-fluorophenyl)benzamide | 179056-10-1

• 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-formyl-N-(4-fluorophenyl)benzamide
• 英文别名: N-(4-fluorophenyl)-4-formylbenzamide
• CAS: 179056-10-1
• 化学式: C₁₄H₁₀FNO₂
• 分子量: 243.237
• InChiKey: PHWIQAVIPXPNMK-UHFFFAOYSA-N

物化性质

• 沸点：
  320.7±27.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 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-formyl-N-(4-fluorophenyl)benzamide 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以82%的产率得到(E)-N-(4-fluorophenyl)-4-((2-isonicotinoylhydrazono)methyl)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-formyl-N-(4-fluorophenyl)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

文献信息

• Amide-type triazole compounds
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20030176480A1

  公开（公告）日：2003-09-18

  A compound of formula (I) or a pharmacologically acceptable prodrug or salt thereof which exhibits excellent antifungal activity: 1 wherein Ar 1 represents a phenyl group or the like; Ar 2 represents a phenylene group or the like. X represents a sulfur atom or a methylene group. R 1 represents a hydrogen atom or a C 1-3 alkyl group; R 2 represents a hydrogen atom or a C 1-3 alkyl group; and R 3 represents an optionally substituted C 6-10 aryl group or the like. Fungal infections may be prevented and/or treated by administering said compound (I) or said prodrug or salt thereof.

  一种具有出色抗真菌活性的化合物，其化学式为（I）或其药理学上可接受的前药或盐：其中Ar1代表苯基或类似物；Ar2代表苯基或类似物。X代表硫原子或亚甲基基团。R1代表氢原子或C1-3烷基基团；R2代表氢原子或C1-3烷基基团；R3代表可选择取代的C6-10芳基基团或类似物。通过给予该化合物（I）或其前药或盐可预防和/或治疗真菌感染。
• TRIAZOLE COMPOUNDS HAVING AMIDE LINKAGE
  申请人：Sankyo Company, Limited

  公开号：EP1284267A1

  公开（公告）日：2003-02-19

  The present invention provides a compound of formula (I) or a pharmacologically acceptable prodrug or salt thereof which exhibits excellent antifungal activity: [wherein Ar1 represents a phenyl group or the like; Ar2 represents a phenylene group or the like; X represents a sulfur atom or a methylene group; R1 represents a hydrogen atom or a C1-3 alkyl group; R2 represents a hydrogen atom or a C1-3 alkyl group; and R3 represents an optionally substituted C6-10 aryl group or the like].

  本发明提供了一种具有优异抗真菌活性的式(I)化合物或其药理学上可接受的原药或盐： [其中 Ar1 代表苯基或类似物；Ar2 代表亚苯基或类似物；X 代表硫原子或亚甲基；R1 代表氢原子或 C1-3 烷基；R2 代表氢原子或 C1-3 烷基；R3 代表任选取代的 C6-10 芳基或类似物]。
• Amide analogs of antifungal dioxane–triazole derivatives: Synthesis and in vitro activities
  作者：Takuya Uchida、Yoshiko Kagoshima、Toshiyuki Konosu

  DOI：10.1016/j.bmcl.2009.02.036

  日期：2009.4

  A new series of triazole compounds possessing an amide-part were efficiently synthesized and their in vitro antifungal activities were investigated. The amide analogs showed excellent in vitro activity against Candida, Cryptococcus and Aspergillus species. The MICs of compound 23d against C. albicans ATCC24433, C. neoformans TIMM1855 and A. fumigatus ATCC26430 were <= 0.008, 0.031 and 0.031 mu g/mL, respectively, (MICs of fluconazole: 0.5, >4 and >4 mu g/mL; MICs of itraconazole: 0.125, 0.25, 0.25 mu g/mL). Furthermore, compound 23d was stable under acidic conditions. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.
• UREA DERIVATIVES AND THEIR USE AS ACAT-INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0784612A1

  公开（公告）日：1997-07-23