4,5-dimethoxy-2-(3-methylfuroxan-4-yl)phenylamine | 924301-64-4

• 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: 4,5-dimethoxy-2-(3-methylfuroxan-4-yl)phenylamine
• 英文别名: 4,5-Dimethoxy-2-(4-methyl-5-oxido-1,2,5-oxadiazol-5-ium-3-yl)aniline
• CAS: 924301-64-4
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: HSJKCKCRDTUFCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-2-(3-methylfuroxan-4-yl)phenylamine 在 盐酸 、 sodium nitrite 、 tin(ll) chloride 作用下， 以 水 为溶剂， 反应 4.0h， 以65%的产率得到4,5-dimethoxy-2-(3-methylfuroxan-4-yl)phenylhydrazine
  参考文献：
  名称：

  Hydrazones and 1,3-Thiazolidin-4-ones Incorporating Furoxan Moiety Synthesized from Eugenol, the Main Constituent of Ocimum sanctum L. Oil

  摘要：

  Two series of new hydrazones and 1,3-thiazolidin-4-ones incorporating furoxan moiety were synthesized from eugenol, the main component of Ocimum sanctum L. oil. The structure of these compounds was determined by IR, MS, H-1 and C-13 NMR analysis. All resonance signals of proton and carbon in the examined compounds are assigned using HSQC, HMBC and NOESY spectra. The hydrazones and the 1,3-thiazolidin-4-ones were tested for antimicrobial activities and almost all examined thiazolidinones displayed moderate activity against S. aureus and A. niger. Among screened hydrazones only one compound exhibited a significant cytotoxicity for human cancer cell line SW620.

  DOI：

  10.3987/com-13-12810
• 作为产物：
  描述：

  4-(2-acetamido-4,5-dimethoxyphenyl)-3-methyl-1,2,5-oxadiazole-2-oxide 在 盐酸 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以72%的产率得到4,5-dimethoxy-2-(3-methylfuroxan-4-yl)phenylamine
  参考文献：
  名称：

  4-（1-氯-1-硝基乙基）-6,7-二甲氧基-2-甲基喹唑啉的合成与转化：一些新型喹唑啉衍生物的光谱表征和抗癌性能

  摘要：

  已经报道了一种高效简单的合成方法，可以合成4-（1-氯-1-硝基乙基）-6,7-二甲氧基-2-甲基喹唑啉（2）作为进一步转化为其他新型6,7-的关键化合物二甲氧基-2-甲基-4-取代的喹唑啉。合成的化合物的结构通过光谱方法表征。提出了一些前所未有的反应的途径。（E）-1-（6,7-二甲氧基-2-甲基喹唑啉-4-基）-3-（4-硝基苯基）丙-2-烯-1-酮（11）对三种细胞系均表现出较高的体外细胞毒性，肝细胞癌（Hep-G2），人肺癌（LU-1）和人乳腺癌（MCF-7），IC 50 分别为2.1、11.6和2.2μM。

  DOI：

  10.1002/jhet.3897

文献信息

• Some imines and azo compounds containing furoxan ring synthesized from methylisoeugenol
  作者：Nguyen Huu Dinh、Ngo Thi Ly、Pham Van Hoan

  DOI：10.1002/jhet.5570430635

  日期：2006.11

  Some imines and azo compounds containing furoxan and benzene rings have been prepared starting from methylisoeugenol. The structure of reported compounds has been confirmed by elemental analysis, ms, uv, ir, and nmr spectroscopy. It is shown that, on treatment with Na2S2O4, the nitro group on the benzene ring was reduced to an amino group, but the N←O group of furoxan ring was not. The 1H- and 13C

  从甲基异丁香酚开始制备了一些含有呋喃喃和苯环的亚胺和偶氮化合物。报告的化合物的结构已通过元素分析，ms，uv，ir和nmr光谱确认。结果表明，在用Na 2 S 2 O 4处理时，苯环上的硝基被还原为氨基，而呋喃喃环上的N←O没有被还原。的1 H-和13个C NMR信号是基于它们的自旋-自旋分裂模式分配，在一些情况下，NOESY和HMBC谱使用。NOESY光谱表明所报道的亚胺具有E-构型。在8种测试化合物中，有5种对Gr +具有抗微生物活性金黄色葡萄球菌的浓度为12.5μg/ mL。
• Synthesis and NMR Spectroscopic Characteristics of Novel Polysubstituted Quinolines Incorporating Furoxan Moiety
  作者：Nguyen Huu Dinh、Trinh Thi Huan、Le Thi Hoa

  DOI：10.3987/com-21-14570

  日期：——

  5,6-Dimethoxy-8-(3-methylfuroxan-4-yl)-2-methylquinoline (1) and 5,6-dimethoxy-8-(3-methylfuroxan-4-yl)quinoline-2-carbaldehyde (2) were synthesized. The condensation of 1 with some nitrobenzaldehydes catalyzed by acetic acid under mild conditions gave four styrylquinolines (1a-d). The condensation of 2 with methyl phenyl ketones catalyzed by potassium hydroxide at room temperature afforded six polysubstituted

  5,6-Dimethoxy-8-(3-methylfuroxan-4-yl)-2-methylquinoline ( 1 ) 和 5,6-dimethoxy-8-(3-methylfuroxan-4-yl)quinoline-2-carbaldehyde ( 2 )被合成了。在温和条件下， 1与一些硝基苯甲醛在乙酸的催化下缩合得到四种苯乙烯基喹啉 ( 1a-d )。在氢氧化钾的催化下， 2与甲基苯基酮在室温下缩合得到六种多取代的 α,β-不饱和酮 ( 2a-f )。基于分析自旋-自旋分裂模式以及它们的 HSQC 和 HMBC 光谱中的交叉峰，分配所获得化合物的所有质子和碳信号。ROESY 谱分析表明，对于 ( E)-3-(quinolin-2-yl)-1-phenylprop-2-en-1-ones Hα 与 Hβ 相比在较弱的场中共振。
• Synthesis and Transformation of 4‐(1‐Chloro‐1‐nitroethyl)‐6,7‐dimethoxy‐2‐methylquinazoline: Spectral Characterization and Anti‐cancer Properties of some Novel Quinazoline Derivatives
  作者：Duong Quoc Hoan、Le Thi Hoa、Trinh Thi Huan、Nguyen Huu Dinh

  DOI：10.1002/jhet.3897

  日期：2020.4

  for the synthesis of 4‐(1‐Chloro‐1‐nitroethyl)‐6,7‐dimethoxy‐2‐methylquinazoline (2) as a key compound for further transformation to other novel 6,7‐dimethoxy‐2‐methyl‐4‐substituted quinazolines. The structure of the synthesized compounds was characterized by spectroscopic methods. The pathway of some unprecedented reactions was proposed. (E)‐1‐(6,7‐dimethoxy‐2‐methylquinazolin‐4‐yl)‐3‐(4‐nitrophenyl)prop‐2‐en‐1‐one

  已经报道了一种高效简单的合成方法，可以合成4-（1-氯-1-硝基乙基）-6,7-二甲氧基-2-甲基喹唑啉（2）作为进一步转化为其他新型6,7-的关键化合物二甲氧基-2-甲基-4-取代的喹唑啉。合成的化合物的结构通过光谱方法表征。提出了一些前所未有的反应的途径。（E）-1-（6,7-二甲氧基-2-甲基喹唑啉-4-基）-3-（4-硝基苯基）丙-2-烯-1-酮（11）对三种细胞系均表现出较高的体外细胞毒性，肝细胞癌（Hep-G2），人肺癌（LU-1）和人乳腺癌（MCF-7），IC 50 分别为2.1、11.6和2.2μM。
• Hydrazones and 1,3-Thiazolidin-4-ones Incorporating Furoxan Moiety Synthesized from Eugenol, the Main Constituent of Ocimum sanctum L. Oil
  作者：Nguyen Huu Dinh、Trinh Thi Huan、Hoang Thi Tuyet Lan、Sang-Bae Han

  DOI：10.3987/com-13-12810

  日期：——

  Two series of new hydrazones and 1,3-thiazolidin-4-ones incorporating furoxan moiety were synthesized from eugenol, the main component of Ocimum sanctum L. oil. The structure of these compounds was determined by IR, MS, H-1 and C-13 NMR analysis. All resonance signals of proton and carbon in the examined compounds are assigned using HSQC, HMBC and NOESY spectra. The hydrazones and the 1,3-thiazolidin-4-ones were tested for antimicrobial activities and almost all examined thiazolidinones displayed moderate activity against S. aureus and A. niger. Among screened hydrazones only one compound exhibited a significant cytotoxicity for human cancer cell line SW620.