N,4-dihydroxy-3-methoxybenzimidoyl chloride | 596095-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,4-dihydroxy-3-methoxybenzimidoyl chloride
• 英文别名: (Z)-N,4-Dihydroxy-3-methoxybenzenecarbonimidoyl chloride；N,4-dihydroxy-3-methoxybenzenecarboximidoyl chloride
• CAS: 596095-21-5
• 化学式: C₈H₈ClNO₃
• 分子量: 201.609
• InChiKey: BGOCCYKFRLZEJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl(2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)vinyl)phenoxy)dimethylsilane 、 N,4-dihydroxy-3-methoxybenzimidoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions

  摘要：

  [3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn (OAc)(3) mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 mu M, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 mu M. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.048
• 作为产物：
  描述：

  香草醛 在 N-氯代丁二酰亚胺 、 盐酸羟胺 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 N,4-dihydroxy-3-methoxybenzimidoyl chloride
  参考文献：
  名称：

  蒙脱土 K-10 上的铜纳米颗粒：一种使用多种方法一锅法合成 3,5-二取代异恶唑的多功能催化剂

  摘要：

  由蒙脱土 K-10 负载的铜纳米颗粒 (CuNPs/MK-10) 组成的易于制备且通用的多相催化剂已被证明在通过各种具有高原子经济性的一锅法方法催化异恶唑的合成方面非常有效。这些方法允许使用容易获得的起始材料，包括通过1,3-偶极环加成反应以及通过炔酮的环异构化得到的醛和炔。此外，CuNPs/MK-10 催化剂通过酰基 Sonogashira 偶联促进了炔酮的原位形成。此外，还开发了一种三步一锅法，从羧酸开始，涉及原位生成酰氯。

  DOI：

  10.1055/a-2193-4701

文献信息

• Synthesis and biological evaluation of novel isoxazole derivatives from acridone
  作者：Mohammed Aarjane、Siham Slassi、Bouchra Tazi、Amina Amine

  DOI：10.1002/ardp.202000261

  日期：2021.3

  The present study was carried out in an attempt to synthesize a new class of potential antibacterial agents. In this context, novel isoxazoles were synthesized and evaluated for their potential antibacterial behavior against four pathogenic bacterial strains. The synthesized compounds exhibited moderate-to-good antibacterial activity against these strains. The highest antibacterial activity was observed

  本研究旨在合成一类新的潜在抗菌剂。在这种情况下，合成了新型异恶唑并评估了它们对四种致病细菌菌株的潜在抗菌行为。合成的化合物对这些菌株表现出中等至良好的抗菌活性。观察到对大肠杆菌菌株的抗菌活性最高，特别是对于异恶唑-吖啶酮骨架上带有苯基和对硝基苯基的化合物 4a 和 4e；与标准药物氯霉素 (22.41 μg/ml) 相比，它们分别显示出有希望的最小抑菌浓度值 16.88 和 19.01 μg/ml。对合成的化合物进行计算机对接研究，以了解它们与大肠杆菌的 DNA 拓扑异构酶复合物（PDB ID：3FV5）相互作用的模式。分子对接结果表明，化合物 4a-l 占据了 DNA 拓扑异构酶（PDB ID：3FV5）的活性位点，通过氢键和疏水相互作用稳定，这可能是其令人感兴趣的体外抗菌活性背后的原因。
• Synthesis and biological evaluation of triazole and isoxazole-tagged benzothiazole/benzoxazole derivatives as potent cytotoxic agents
  作者：Tulshiram L. Dadmal、K. Appalanaidu、Ravindra M. Kumbhare、Tanmoy Mondal、M. Janaki Ramaiah、Manika Pal Bhadra

  DOI：10.1039/c8nj01249k

  日期：——

  isoxazole-linked benzothiazole/benzoxazole derivatives were synthesized and evaluated for their anticancer activity against human cancer cell lines, such as HeLa (cervical), and A549 (lung) cell lines, with HEK-293 cell line used as a control. Among them, conjugates 8a, 8f, 13g, 13h and 13j displayed significant cytotoxic activity against human cancer cell lines. Furthermore, these active conjugates induced

  癌症是人类的主要健康问题，也是最令人不安的疾病，在发达国家和发展中国家均会导致死亡。正确治疗该疾病仍然是一个挑战。化学疗法被认为是治愈该疾病的方法之一。在这项研究中，合成了一系列1,2,3-三唑和异恶唑连接的苯并噻唑/苯并恶唑衍生物，并评估了其对人癌细胞系（例如HeLa（宫颈）和A549（肺）细胞系）的抗癌活性。 ，以HEK-293细胞系为对照。其中，缀合物8a，8f，13g，13h和13j对人类癌细胞系显示出显着的细胞毒活性。此外，这些活性缀合物诱导与凋亡的内在途径有关的关键凋亡基因如caspase-9，caspase-3，BAX和细胞色素c的表达增加。这项研究可能为HeLa和肺癌细胞提供可能的抗癌疗法。
• Discovery of 3-Amino-4-Chlorophenyl P1 as a novel and potent benzamidine mimic via solid-phase synthesis of an isoxazoline library
  作者：Patrick Y.S. Lam、Jessica J. Adams、Charles G. Clark、W.Jason Calhoun、Joseph M. Luettgen、Robert M. Knabb、Ruth R. Wexler

  DOI：10.1016/s0960-894x(03)00130-6

  日期：2003.5

  In an effort to identify orally bioavailable factor Xa inhibitors, two isoxazolines libraries were prepared to scan for novel P1 ligands. From this work, 4-chloro-3-aniline was identified as a novel and potent benzamidine mimic. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and bio-evaluation of human macrophage migration inhibitory factor inhibitor to develop anti-inflammatory agent
  作者：Athar Alam、Chinmay Pal、Manish Goyal、Milan Kumar Kundu、Rahul Kumar、Mohd Shameel Iqbal、Sumanta Dey、Samik Bindu、Souvik Sarkar、Uttam Pal、Nakul C. Maiti、Susanta Adhikari、Uday Bandyopadhyay

  DOI：10.1016/j.bmc.2011.10.056

  日期：2011.12

  Macrophage migration inhibitory factor (MIF), a pro-inflammatory cytokine, is involved in the development of an array of inflammatory disorders including rheumatoid arthritis, inflammatory bowel disease, psoriasis, multiple sclerosis and sepsis. The synthesis of MIF-inhibitor is a rationale approach to develop novel anti-inflammatory agent to treat multitude of inflammatory diseases. In this work, we have synthesized and evaluated MIF-inhibitory activity of a series of small molecules containing isoxazoline skeleton. Mode of binding of this inhibitor to human MIF (huMIF) was determined by docking studies. The synthesized molecules inhibit tautomerase activity of huMIF. The anti-inflammatory activity of the most active inhibitor, 4-((3-(4-hydroxy-3-methoxyphenyl)-4, 5-dihydroisoxazol-5-yl) methoxy) benzaldehyde (4b) was evaluated against huMIF-induced inflammation in a cellular model (RAW 264.7 cell). Compound 4b significantly inhibits huMIF-mediated NF-kappa B translocation to the nucleus, up-regulation of inducible nitric oxide synthase and nitric oxide production in RAW 264.7 cell which are the markers for inflammation. The compound 4b is not cytotoxic as evident from cell viability assay. Hence, the compound 4b has potential to be a novel anti-inflammatory agent. (C) 2011 Elsevier Ltd. All rights reserved.