4-chloro-2-(4-chlorophenoxy)aniline | 56966-49-5

• 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-chloro-2-(4-chlorophenoxy)aniline
• 英文别名: 4-Chloro-2-(4-chlorophenoxy)aniline
• CAS: 56966-49-5
• 化学式: C₁₂H₉Cl₂NO
• 分子量: 254.116
• InChiKey: HDGZIHCCEYFXMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(4-chlorophenoxy)aniline 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 N-[4-chloro-2-(4-chlorophenoxy)phenyl]-2-hydroxy-4-oxo-1,5-dioxaspiro[5.5]undec-2-ene-3-carboxamide
  参考文献：
  名称：

  A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides

  摘要：

  Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A(2) from human polymorphonuclear leucocytes (h-PMN PLA(2)). Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 mu M) were found in the series of 2,4-disubstituted phenyl analogues of a. Compound 1a was selected for evaluation of its biological profile. This substance potently inhibited secretory PLA(2)s from several sources other than human PMNs, with a clear preference for group II over group I PLA(2), whereas human cytosolic PLA(2) and phospholipase C were not significantly affected. Inhibition of h-PMN PLA(2) was calcium-dependent. In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA(2) as an underlying mechanism. In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds.

  DOI：

  10.1016/0223-5234(94)90026-4
• 作为产物：
  描述：

  4-chloro-2-(4-chlorophenoxy)-1-nitrobenzene 在 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 生成 4-chloro-2-(4-chlorophenoxy)aniline
  参考文献：
  名称：

  含二苯醚片段的烟酰胺衍生物作为潜在的琥珀酸脱氢酶抑制剂的合成、生物活性评价和理论研究

  摘要：

  为了获得对立枯丝核菌具有较高抑制活性的烟酰胺类杀菌剂，通过将二苯醚片段引入啶酰菌胺的结构中，设计合成了 24 种烟酰胺衍生物。生物测定表明，获得的化合物表现出不同程度的抗真菌活性。其中，化合物 2-氯-N-（2-（2-4-二氯苯氧基）苯基）烟酰胺 （7g） 对立枯菌表现出显著的生物活性 （EC50 = 0.034 mg/L），超过啶酰菌胺的抑制作用。实验上，化合物 7g 是一种很有前途的低毒性杀菌剂，靶向琥珀酸脱氢酶，细胞毒性、酶活性抑制、线粒体膜电位和菌丝呼吸试验证实了这一点。本研究强调了含有二苯醚片段的烟酰胺衍生物的潜力，这些衍生物基于理论计算设计为琥珀酸脱氢酶抑制剂 （SDHI） 杀菌剂。

  DOI：

  10.1016/j.molstruc.2024.138331

文献信息

• 一种含二苯醚基的噻唑酰胺类化合物及其制备方法与应用
  申请人：安徽理工大学

  公开号：CN114560826A

  公开（公告）日：2022-05-31

  本发明属于杀菌剂领域。涉及一种含二苯醚基的噻唑酰胺类化合物及其在防治农业真菌性病害中的应用。其中，所述含二苯醚基的噻唑酰胺类化合物的结构如通式I所示：通式I中各取代基定义见说明书。本发明通式I化合物具有优异的杀菌活性，可在农业生产中用于防治真菌病害。
• Synthesis and Anti‐Fungal/Oomycete Activity of Novel Sulfonamide Derivatives Containing Camphor Scaffold
  作者：Zihui Yang、Xuebao Sun、Daojun Jin、Yigui Qiu、Linlin Chen、Lu Sun、Wen Gu

  DOI：10.1002/cbdv.202200608

  日期：2022.10

  Twelve novel camphor sulfonamide derivatives 2a–2l were synthesized and characterized by 1H-NMR, 13C-NMR and HRMS spectra. The anti-fungal/oomycete activity bioassay showed that some of the title compounds displayed moderate to good anti-fungal/oomycete activities against B. dothidea and P. capsici. Compound 2d exhibited the best in vitro antifungal activity toward B. dothidea. The in vivo experiment

  合成了12 种新型樟脑磺酰胺衍生物2a – 2l，并通过1 H-NMR、13 C-NMR 和 HRMS 光谱对其进行了表征。抗真菌/卵菌活性生物测定表明，一些标题化合物对B. dothidea和P. capsici表现出中等至良好的抗真菌/卵菌活性。化合物2d对B. dothidea表现出最好的体外抗真菌活性。体内实验表明，化合物2d在200 mg/L时具有相当大的抗B. dothidea作用。机理研究表明，复合2d可增加细胞膜通透性。此外，体外酶抑制试验和分子对接结果表明化合物2d可能是一种潜在的SDH抑制剂。
• DE506339
  申请人：——

  公开号：——

  公开（公告）日：——
• Wardrop,A.W.H. et al., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1279 - 1285
  作者：Wardrop,A.W.H. et al.

  DOI：——

  日期：——
• A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides
  作者：W Breitenstein、F Märki、S Roggo、I Wiesenberg、J Pfeilschifter、P Furet、E Beriger

  DOI：10.1016/0223-5234(94)90026-4

  日期：1994.1

  Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A(2) from human polymorphonuclear leucocytes (h-PMN PLA(2)). Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 mu M) were found in the series of 2,4-disubstituted phenyl analogues of a. Compound 1a was selected for evaluation of its biological profile. This substance potently inhibited secretory PLA(2)s from several sources other than human PMNs, with a clear preference for group II over group I PLA(2), whereas human cytosolic PLA(2) and phospholipase C were not significantly affected. Inhibition of h-PMN PLA(2) was calcium-dependent. In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA(2) as an underlying mechanism. In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds.