(E)-2-methoxy-4-(prop-1-enyl)-1-(prop-2-ynyloxy)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-2-methoxy-4-(prop-1-enyl)-1-(prop-2-ynyloxy)benzene
• 英文别名: (E)-2-methoxy-4-(prop-1-en-1-yl)-1-(prop-2-yn-1-yloxy)benzene；2-methoxy-4-[(E)-prop-1-enyl]-1-prop-2-ynoxybenzene
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: FLIVWSGASUONIF-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-methoxy-4-(prop-1-enyl)-1-(prop-2-ynyloxy)benzene 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  1,3-二炔作为强效抗烟曲霉抗真菌剂的设计与合成

  摘要：

  1,3-二炔通过Glaser-Hay 和 Cadiot-Chodkiewicz 偶联反应合成，以提供有效的抗真菌剂。所有化合物都针对致病真菌烟曲霉进行了评估，发现一种化合物特别具有良好的抗真菌活性，表明这种类型的支架适用于开发新的抗真菌剂。最活跃的化合物还表现出显着的抗生物膜活性。是 CSIR 研究所突出研究的联合特别收藏的一部分。

  DOI：

  10.1002/cmdc.202300013
• 作为产物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 (E)-2-methoxy-4-(prop-1-enyl)-1-(prop-2-ynyloxy)benzene
  参考文献：
  名称：

  1,3-二炔作为强效抗烟曲霉抗真菌剂的设计与合成

  摘要：

  1,3-二炔通过Glaser-Hay 和 Cadiot-Chodkiewicz 偶联反应合成，以提供有效的抗真菌剂。所有化合物都针对致病真菌烟曲霉进行了评估，发现一种化合物特别具有良好的抗真菌活性，表明这种类型的支架适用于开发新的抗真菌剂。最活跃的化合物还表现出显着的抗生物膜活性。是 CSIR 研究所突出研究的联合特别收藏的一部分。

  DOI：

  10.1002/cmdc.202300013

文献信息

• Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against <i>Aspergillus fumigatus</i>
  作者：Lakshmi Goswami、Lovely Gupta、Sayantan Paul、Maansi Vermani、Pooja Vijayaraghavan、Asish K. Bhattacharya

  DOI：10.1039/d2md00138a

  日期：——

  complexity. The secondary metabolites of the plant Myristica fragrans, eugenol and isoeugenol, have shown antifungal activities (IC50 1900 μM). Therefore, we envisioned that glycoconjugates based on these two scaffolds could prove to be potent antifungal agents. Triazole-containing compounds have shown prominent activities as antifungal agents. Based on this, we opined that a Cu(I) catalyzed click reaction

  糖缀合物是具有生物学意义的分子，因为它们根据其大小和复杂性往往服务于广泛的细胞内和细胞外过程。肉豆蔻植物的次生代谢物丁子香酚和异丁子香酚已显示出抗真菌活性 (IC 50 1900 μM)。因此，我们设想基于这两种支架的糖复合物可能被证明是有效的抗真菌剂。含三唑的化合物已显示出作为抗真菌剂的显着活性。基于此，我们认为Cu( I )催化的点击反应可以作为丁香酚/异丁香酚部分和糖之间的桥接工具来合成基于丁子香酚/异丁香酚的糖复合物。在我们目前的工作中，我们将炔丙化丁香酚/异丁香酚和叠氮糖偶联以提供基于丁香酚/异丁香酚的糖复合物。在另一种方法中，我们对丁子香酚的双键进行羟基化，随后对伯醇进行叠氮化，然后进行分子内偶联反应，产生各种其他类似物。所有合成的化合物均针对机会性致病真菌烟曲霉进行了测定。在合成的化合物中，两种类似物表现出显着的抗真菌活性，IC 50值分别为5.42 和9.39 μM。研究表
• Kojic acid–natural product conjugates as mushroom tyrosinase inhibitors
  作者：Morteza Ashooriha、Mehdi Khoshneviszadeh、Mahsima Khoshneviszadeh、Alireza Rafiei、Mostafa Kardan、Rezvan Yazdian-Robati、Saeed Emami

  DOI：10.1016/j.ejmech.2020.112480

  日期：2020.9

  As part of our effort to develop potential tyrosinase inhibitors, we have conjugated the well-known tyrosinase inhibitor kojic acid (KA) with several phenolic natural products such as umbelliferone, sesamol, thymol, carvacrol, eugenol, isoeugenol, vanillin, isovanillin, and apocynin that some reports have shown their activity on tyrosinase enzyme. The designed compounds were synthesized using click reaction and 1,2,3-triazole formation. All compound showed potent anti-tyrosinase activity significantly higher than KA. The best activities were observed with apocynin and 4-coumarinol analogs (10c and 16c) displaying IC50 values of 0.03 and 0.02 mu M, respectively. The potency of 16c was >460-times more than that of KA. Cell-based assays against B16F10 and HFF cells revealed that the representative compounds can efficiently suppress the melanogenesis without significant toxicity on cells. (C) 2020 Elsevier Masson SAS. All rights reserved.
• Synthesis, QSAR and anticandidal evaluation of 1,2,3-triazoles derived from naturally bioactive scaffolds
  作者：Mohammad Irfan、Babita Aneja、Umesh Yadava、Shabana I. Khan、Nikhat Manzoor、Constantin G. Daniliuc、Mohammad Abid

  DOI：10.1016/j.ejmech.2015.02.007

  日期：2015.3

  In the present study, we used eight natural precursors (1a-h) with most of them having promising antimicrobial activities and synthesised their novel 1,2,3-triazole derivatives (3a-h). In the reaction sequences, the precursor compounds (1a-h) were converted to their respective alkyne (2a-h) followed by addition of benzyl azide freshly prepared by the reaction of benzyl bromide with sodium azide using [3 + 2] azide-alkyne cycloaddition strategy. Structural elucidation of all the triazole derivatives was done using FT-IR, H-1, C-13 NMR, mass and elemental analysis techniques. The single crystal X-ray diffraction for 3d was also recorded. The result of in vitro anticandidal activity performed against three different strains of Candida showed that compound 3e was found superior/comparable to fluconazole (FLC) with IC50 values of 0.044 mu g/mL against Candida albicans (ATCC 90028), 12.022 mu g/mL against Candida glabrata (ATCC 90030), and 3.60 mu g/mL against Candida tropicalis (ATCC 750). Moreover, at their IC50 values, compounds 3e and 3h showed <5% hemolysis which indicates the non-toxic behaviour of these inhibitors. Cytotoxicity assay was also performed on VERO cell line and all the derivatives were found nontoxic up to the concentration of 10.0 mu g/mL. The in silico technique of 3D-QSAR was applied to establish structure activity relationship of the synthesized compounds. The results reveal the molecular fragments that play an essential role in improving the anticandidal activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Design and Synthesis of 1,3‐Diynes as Potent Antifungal Agents against <i>Aspergillus fumigatus</i>
  作者：Lakshmi Goswami、Lovely Gupta、Sayantan Paul、Pooja Vijayaraghavan、Asish K. Bhattacharya

  DOI：10.1002/cmdc.202300013

  日期：——

  1,3-Diynes were synthesized via Glaser-Hay and Cadiot-Chodkiewicz coupling reactions to furnish potent antifungal agents. All compounds were evaluated against the pathogenic fungus, A. fumigatus, and one compound in particular was found to exhibit promising antifungal activity, suggesting this type of scaffold to be suitable for developing new antifungal agents. The most active compound also exhibited

  1,3-二炔通过Glaser-Hay 和 Cadiot-Chodkiewicz 偶联反应合成，以提供有效的抗真菌剂。所有化合物都针对致病真菌烟曲霉进行了评估，发现一种化合物特别具有良好的抗真菌活性，表明这种类型的支架适用于开发新的抗真菌剂。最活跃的化合物还表现出显着的抗生物膜活性。是 CSIR 研究所突出研究的联合特别收藏的一部分。