4-allyl-2-methoxyphenyl 4-chlorobenzoate | 80138-44-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-allyl-2-methoxyphenyl 4-chlorobenzoate
• 英文别名: 2-Methoxy-4-(prop-2-en-1-yl)phenyl 4-chlorobenzoate；(2-methoxy-4-prop-2-enylphenyl) 4-chlorobenzoate
• CAS: 80138-44-9
• 化学式: C₁₇H₁₅ClO₃
• 分子量: 302.757
• InChiKey: DZHQZZMUUWVQRR-UHFFFAOYSA-N

物化性质

• 沸点：
  457.3±45.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯甲酸 在 三溴甲基苯砜 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 4-allyl-2-methoxyphenyl 4-chlorobenzoate
  参考文献：
  名称：

  新型 1-磺酰氧基/酰氧基丁香酚衍生物作为杀菌剂的组合合成

  摘要：

  背景： 开发高效、低风险的小分子绿色杀菌剂是有效控制植物病原真菌的关键。精油因其独特的来源和潜在的靶点，在新型杀菌剂发现中发挥着非常重要的作用。丁香酚是一种植物精油，主要从桃金娘科的丁香属植物的未开放和干燥的花蕾中分离得到。由于其独特的结构骨架，丁香酚及其衍生物展现出了广泛的生物活性。然而，关于合成新型1-磺酰氧基/酰氧基丁香酚衍生物作为对辣椒疫霉菌的杀菌剂的研究尚未报道。 方法： 制备了26种新型1-磺酰氧基/酰氧基丁香酚衍生物（3a-p和5a-j），并通过1H NMR、HRMS和熔点对其结构进行了良好的表征。使用菌丝生长速率法评估了它们对辣椒疫霉菌的杀菌活性。 结果： 为了寻找控制植物病原真菌的新型天然产物杀菌剂，我们设计和合成了两系列新型1-磺酰氧基/酰氧基丁香酚衍生物（3a-p和5a-j）作为对辣椒疫霉菌的杀菌剂。杀菌活性结果显示，在所有化合物中，特别是化合物3a、3f和3n，对辣椒疫霉菌的抗真菌活性最强，EC50值分别为79.05、75.05和70.80。 结论： 结果表明，磺酰氧基的丁香酚的抗真菌活性高于酰氧基。建议通过引入磺酰氧基来提高丁香酚的杀菌活性。这将为进一步设计、结构修饰和开发丁香酚衍生物作为杀菌剂铺平道路。

  DOI：

  10.2174/1386207324666210813114829

文献信息

• Synthesis and Antibacterial Study of Eugenol Derivatives
  作者：Nurul Hazwani Che Abdul Rahim、Asnuzilawati Asari、Noraznawati Ismail、Hasnah Osman

  DOI：10.14233/ajchem.2017.20100

  日期：——

  A series of eugenol derivatives (2-14) were synthesized and evaluated for their antibacterial activity against five bacterial test strains; three Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus and Staphylococcus epidermidis) and two Gram-negative bacteria (Escherichia coli and Salmonella typhimurium) using well-diffusion method. Among the compounds tested, compounds 2-4 displayed susceptible activity toward S. epidermidis with 16-18 mm whereas compounds 12 exhibited susceptible inhibition towards S. aureus only with inhibition diameter of 16 mm, respectively. Other compounds possessed varied antibacterial activities classified as intermediate or resistance indicating that eugenol derivatives have narrow spectrum activity and specifically to Gram-positive bacteria.

  研究人员合成了一系列丁香酚衍生物（2-14），并采用井扩散法评估了它们对五种细菌试验菌株（三种革兰氏阳性菌（枯草杆菌、金黄色葡萄球菌和表皮葡萄球菌）和两种革兰氏阴性菌（大肠杆菌和鼠伤寒沙门氏菌））的抗菌活性。在测试的化合物中，化合物 2-4 对表皮葡萄球菌具有易感活性，抑制直径为 16-18 mm，而化合物 12 只对金黄色葡萄球菌具有易感抑制活性，抑制直径为 16 mm。其他化合物具有不同的抗菌活性，分为中间活性和抗性活性，这表明丁香酚衍生物具有窄谱活性，专门针对革兰氏阳性菌。
• Structural modification of naturally occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells
  作者：Pedro Olim、Renato B. Pereira、Maria José G. Fernandes、Carolina M. Natal、José R. A. Coelho、A. Gil Fortes、M. Sameiro T. Gonçalves、David M. Pereira

  DOI：10.1002/ardp.202300294

  日期：2023.12

  Natural products belonging to different chemical classes have been established as a promising source of novel anticancer drugs. Several low‐molecular‐weight compounds from the classes of monoterpenes, phenylpropanoids, and flavonoids were shown to possess anticancer activities in previous studies. In this work, over 20 semisynthetic derivatives of molecules belonging to these classes, namely thymol, eugenol, and 6‐hydroxyflavanone were synthesized and tested for their cytotoxicity against two human cancer cell lines, namely AGS cells (gastric adenocarcinoma) and A549 cells (human lung carcinoma). An initial screening based on viability assessment was performed to identify the most cytotoxic compounds at 100 μM. The results evidenced that two 6‐hydroxyflavanone derivatives were the most cytotoxic among the compounds tested, being selected for further studies. These derivatives displayed enhanced toxicity when compared with their natural counterparts. Moreover, the lactate dehydrogenase (LDH) assay showed that the loss of cell viability was not accompanied by a loss of membrane integrity, thus ruling out a necrotic process. Morphological studies with AGS cells demonstrated chromatin condensation compatible with apoptosis, confirmed by the activation of caspase 3/7. Furthermore, a viability assay on a noncancer human embryonic lung fibroblast cell line (MRC‐5) confirmed that these two derivatives possess selective anticancer activity.

  摘要 属于不同化学类别的天然产品已被确定为新型抗癌药物的一种有前途的来源。以往的研究表明，单萜、苯丙酮类和黄酮类中的一些低分子量化合物具有抗癌活性。在这项工作中，合成了属于这些类别的分子（即百里酚、丁香酚和 6-羟基黄烷酮）的 20 多种半合成衍生物，并测试了它们对两种人类癌细胞系（即 AGS 细胞（胃腺癌）和 A549 细胞（人类肺癌））的细胞毒性。根据活力评估进行了初步筛选，以确定细胞毒性最强的 100 μM 化合物。结果表明，两种 6-羟基黄烷酮衍生物在所测试的化合物中细胞毒性最强，因此被选作进一步研究的对象。与天然对应物相比，这些衍生物显示出更强的毒性。此外，乳酸脱氢酶（LDH）测定显示，细胞活力的丧失并没有伴随着膜完整性的丧失，因此排除了坏死过程的可能性。对 AGS 细胞进行的形态学研究表明，染色质凝集与细胞凋亡相符，并通过 caspase 3/7 的激活得到证实。此外，对非癌人类胚胎肺成纤维细胞系（MRC-5）进行的存活率检测证实，这两种衍生物具有选择性抗癌活性。
• Design and synthesis of eugenol derivatives, as potent 15-lipoxygenase inhibitors
  作者：Hamid Sadeghian、Seyed Mohammad Seyedi、Mohammad Reza Saberi、Zahra Arghiani、Mehdi Riazi

  DOI：10.1016/j.bmc.2007.10.016

  日期：2008.1

  A group of 4-allyl-2-methoxyphenol (eugenol) esters were designed, synthesized, and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO). Compounds 4c, 4d 4f, 4p, and 4q showed the best IC50 in SLO inhibition (IC50 = 1.7, 2.3, 2.1, 2.2, and 0.017 mu M respectively). All compounds were docked into SLO active site and showed that ally) group of compounds is oriented toward the iron atom in the active site of SLO. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of eugenol derivatives in inhibiting 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques. (C) 2007 Elsevier Ltd. All rights reserved.
• 1-(4-Chlorobenzoyloxy)-2-methoxy-4-(2-propenyl)benzene
  作者：M. Aygün、Ş. Işik、S. Şaşmaz、M. N. Tahir、A. Erdönmez、O. Büyükgüngör

  DOI：10.1107/s0108270197000553

  日期：1997.7.15

  In the title compound, 2-methoxy-4-(2-propenyl)phenyl 4-chlorobenzoate, C17H15ClO3, the allyl group is observed to be in a disordered state. The two C atoms of the allyl group occupy two sets of sites in unequal proportions (68:32). The dihedral angle between the two aromatic rings is 71.64(10)degrees.
• MATHIEU, A.;BLUM, J.
  作者：MATHIEU, A.、BLUM, J.

  DOI：——

  日期：——