N-(3-chlorophenyl)-2-(4-formylphenoxy)acetamide | 574711-99-2

• 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: N-(3-chlorophenyl)-2-(4-formylphenoxy)acetamide
• 英文别名: 4-[4-(3-chlorophenyl)-3-aza-2-oxo-propyloxy] benzaldehyde
• CAS: 574711-99-2
• 化学式: C₁₅H₁₂ClNO₃
• 分子量: 289.718
• InChiKey: CQXQMLMRGLEDSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 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：

  巴比妥酸 、 N-(3-chlorophenyl)-2-(4-formylphenoxy)acetamide 以 乙醇 、 水 为溶剂， 以95%的产率得到N-(3-chlorophenyl)-2-(4-((2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)methyl)phenoxy)acetamide
  参考文献：
  名称：

  Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease

  摘要：

  Forty-four barbituric acid or thiobarbituric acid derivatives were synthesized and evaluated for their effects on adipogenesis of 3T3-L1 adipocytes by measuring the expression of adiponectin in vitro. Four compounds (3a, 30, 3s, 4t) were found to increase the expression of adiponectin and lower the leptin level in 31341 adipocytes at respective concentration of 10 mu M. Among them, 3s showed the most efficacious. Oral administration of 3s effectively reduced body weight, liver weight, and visceral fat and regulated serum levels of biochemical markers in the high-fat/diet-induced Wistar rats. Histopathological evaluation of liver sections by Oil Red O and H&E staining confirmed 3s as a potent, orally active molecule for reducing fat deposition against non-alcoholic fatty liver disease. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.033
• 作为产物：
  描述：

  N1-(3-氯苯基)-2-氯乙胺 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 N-(3-chlorophenyl)-2-(4-formylphenoxy)acetamide
  参考文献：
  名称：

  Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases

  摘要：

  In our previous work, 3I inhibited the LPS-induced iNOS activity and NO production in RAW 264.7 cells and improved joint inflammation and cartilage destruction in inflammatory model. In this study, we synthesized 59 derivatives and bioisosteres on the basis of 3I by Knoevenagel condensation and biologically evaluated for the study of structure-activity relationship (SAR). We found that 7-44 suppressed the iNOS activity (IC50 25.2 mu M) and LPS-induced NO production (IC50 45.6 mu M) in RAW 264.7 cells. As for the SAR study, the dimethoxylphenyl group of 7-44 was potential for a further modification. At a dose of 10 mg/kg, oral administration of 7-44 possessed protective properties in both carrageenan-induced paw edema of male ICR mice and adjuvant-induced arthritis of Lewis female rats. Although the activity of 7-44 was slightly inferior, the PK profiles of 7-44 were superior to those of 3I. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.036

文献信息

• N-Heterocycles Scaffolds as Quorum Sensing Inhibitors. Design, Synthesis, Biological and Docking Studies
  作者：Alfredo Fuentes-Gutiérrez、Everardo Curiel-Quesada、José Correa-Basurto、Alberto Martínez-Muñoz、Alicia Reyes-Arellano

  DOI：10.3390/ijms21249512

  日期：——

  Quorum sensing is a communication system among bacteria to sense the proper time to express their virulence factors. Quorum sensing inhibition is a therapeutic strategy to block bacterial mechanisms of virulence. The aim of this study was to synthesize and evaluate new bioisosteres of N-acyl homoserine lactones as Quorum sensing inhibitors in Chromobacterium violaceum CV026 by quantifying the specific production of violacein. Five series of compounds with different heterocyclic scaffolds were synthesized in good yields: thiazoles, 16a–c, thiazolines 17a–c, benzimidazoles 18a–c, pyridines 19a–c and imidazolines 32a–c. All 15 compounds showed activity as Quorum sensing inhibitors except 16a. Compounds 16b, 17a–c, 18a, 18c, 19c and 32b exhibited activity at concentrations of 10 µM and 100 µM, highlighting the activity of benzimidazole 18a (IC50 = 36.67 µM) and 32b (IC50 = 85.03 µM). Pyridine 19c displayed the best quorum sensing inhibition activity (IC50 = 9.66 µM). Molecular docking simulations were conducted for all test compounds on the Chromobacterium violaceum CviR protein to gain insight into the process of quorum sensing inhibition. The in-silico data reveal that all 15 the compounds have higher affinity for the protein than the native AHL ligand (1). A strong correlation was found between the theoretical and experimental results.

  广义上说，群体感知是细菌之间的一种通信系统，用于感知适当的时间来表达它们的毒力因子。群体感知抑制是一种阻断细菌毒力机制的治疗策略。本研究旨在合成和评估新的N-酰基同源半乳糖酮类生物同构体，作为Chromobacterium violaceum CV026中群体感知抑制剂，通过定量测定紫色素的特定产量。合成了五个不同杂环骨架的化合物系列，产率良好：噻唑类化合物16a–c，噻唑啉类17a–c，苯并咪唑类18a–c，吡啶类19a–c和咪唑啉类32a–c。所有15个化合物都显示出作为群体感知抑制剂的活性，除了16a。化合物16b，17a–c，18a，18c，19c和32b在浓度为10 µM和100 µM时表现出活性，突出显示了苯并咪唑18a（IC50 = 36.67 µM）和32b（IC50 = 85.03 µM）的活性。吡啶19c显示出最佳的群体感知抑制活性（IC50 = 9.66 µM）。对所有测试化合物在Chromobacterium violaceum CviR蛋白上进行了分子对接模拟，以深入了解群体感知抑制的过程。计算机辅助数据显示，所有15个化合物与蛋白的亲和力均高于天然的AHL配体（1）。理论结果与实验结果之间存在较强的相关性。
• Chitosan and functionalized graphene oxide nanocomposite as a novel and highly efficient catalyst for production of bis-coumarins under solvent-free conditions
  作者：Zhale Atashrouz、Esmael Rostami、Abdolkarim Zare

  DOI：10.1007/s11164-021-04616-2

  日期：2022.1

  Afterward, graphene oxide was modified by aliphatic amine and then with dithioglycolic acid, giving rise to thiol (SH)-functionalized graphene oxide after reduction. The nanocomposite was prepared from the reaction of 2-chloroacetyl-functionalized chitosan and thiol-modified graphene oxide, followed by oxidization of thiols to SO 3 H groups using hydrogen peroxide. The nanocomposite (catalyst) was

  壳聚糖和功能化的氧化石墨烯纳米复合材料被用作高效、可持续和可回收的催化剂，用于在无溶剂条件下使用 4-羟基香豆素和芳香醛生产双香豆素。首先使用氯乙酰氯对壳聚糖进行功能化。之后，用脂肪胺和二硫代乙醇酸对氧化石墨烯进行改性，还原后产生硫醇（SH）官能化的氧化石墨烯。该纳米复合材料由 2-氯乙酰官能化壳聚糖和硫醇改性氧化石墨烯反应制备，然后使用过氧化氢将硫醇氧化为 SO 3 H 基团。使用场发射扫描电子显微镜、能量色散 X 射线光谱、X 射线衍射、热重分析、差示热重分析、FT-IR 和 MAP 分析。与之前报道的纳米复合材料相比，该纳米复合材料表现出优越的性能，包括无毒、环境相容性、无溶剂条件、简单的后处理、无副产物、热稳定性和可回收性。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• Synthesis and Biological Evaluation of Novel 5-Benzylidenethiazolidine-2,4-dione Derivatives for the Treatment of Inflammatory Diseases
  作者：Liang Ma、Caifeng Xie、Yinghua Ma、Juan Liu、Mingli Xiang、Xia Ye、Hao Zheng、Zhizhi Chen、Qinyuan Xu、Tao Chen、Jinying Chen、Jincheng Yang、Neng Qiu、Guangcheng Wang、Xiaolin Liang、Aihua Peng、Shengyong Yang、Yuquan Wei、Lijuan Chen

  DOI：10.1021/jm1011534

  日期：2011.4.14

  Twenty-two compounds based on thiazolidine-2,4-dione moiety were synthesized and evaluated for the inhibitory potency on the production of nitric oxide (NO), inducible nitric oxide synthase (iNOS) activity, and the generation of prostaglandin E-2 (PEG(2)). (Z)-N-(3-Chlorophenyl)-2-(4-((2,4-dioxothiazolidin-5-ylidene) methyl) phenoxy) acetamide (3I), superior to the commercial anti-inflammatory drug indomethacin, significantly inhibited iNOS activity (IC50 = 8.66 mu M), iNOS-mediated NO, and cyclooxnenase (COX)-2-derived PGE(2) production (IC50 = 4.16 and 23.55 mu M, respectively) on lipopolysaccharide (LPS)-induced. RAW 264.7 cells. Docking study revealed that 3I was perfectly docking into the active site of murine iNOS and suppressed the expression of iNOS protein as evidenced by Western blot analysis. At the dose of 50 mg/kg, oral administration of 3I possessed protective properties in both carrageenan-induced paw edema and adjuvant-induced arthritis rat models.
• Cink4T, a quinazolinone-based dual inhibitor of Cdk4 and tubulin polymerization, identified via ligand-based virtual screening, for efficient anticancer therapy
  作者：Vinay Sonawane、Mohd Usman Mohd Siddique、Surender Singh Jadav、Barij Nayan Sinha、Venkatesan Jayaprakash、Bhabatosh Chaudhuri

  DOI：10.1016/j.ejmech.2019.01.011

  日期：2019.3

  Inhibition of cyclin dependent kinase 4 (Cdk4) prevents cancer cells from entering the early G(0)/G(1) phase of the cell division cycle whereas inhibiting tubulin polymerization blocks cancer cells' ability to undergo mitosis (M) late in the cell cycle. We had reported earlier that two non-planar and relatively non-toxic fascaplysin derivatives, an indole and a tryptoline, inhibit Cdk4 with IC50 values of 6.2 and 10 mu M, respectively. Serendipitously, we had also found that they inhibited tubulin polymerization. The molecules were efficacious in mouse tumor models. We have now identified Cink4T in a 59-compound quinazolinone library, designed on the basis of ligand-based virtual screening, as a compound that inhibits Cdk4 and tubulin. Its IC50 value for Cdk4 inhibition is 0.47 mu M and >50 mu M for inhibition of Cdk1, Cdk2, Cdk6, Cdk9. Cink4T inhibits tubulin polymerization with an IC50 of 0.6 mu M. Molecular modelling studies on Cink4T with Cdk4 and tubulin crystal structures lend support to these observations. Cancer cell cycle analyses confirm that Cink4T blocks cells at both G(0)/G(1) and M phases as it should if it were to inhibit both Cdk4 and tubulin polymerization. Our results show, for the very first time, that virtual screening can be used to design novel inhibitors that can potently block two crucial phases of the cell division cycle. (C) 2019 Elsevier Masson SAS. All rights reserved.