(E)-4-[3-methoxy-4-(3-methylbutoxy)phenyl]but-3-en-2-one | 915287-60-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-[3-methoxy-4-(3-methylbutoxy)phenyl]but-3-en-2-one
• CAS: 915287-60-4
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: JIFOOXPGPFSQIY-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-[3-methoxy-4-(3-methylbutoxy)phenyl]but-3-en-2-one 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 3.0h， 以78%的产率得到1-{2-[3-methoxy-4-(3-methylbutoxy)phenyl]cyclopropyl}ethanone
  参考文献：
  名称：

  基于脱氢姜油酮的环丙基衍生物的细胞毒性和抗菌活性

  摘要：

  以脱氢姜酮（4-（4-羟基-3-甲氧基苯基）-3-丁烯-2-酮）及其O为原料，制备了一系列1-乙酰基-2-（4-烷氧基-3-甲氧基苯基）环丙烷-烷基衍生物。测试了它们对某些细菌和真菌菌株的微生物活性，以及​​它们对某些癌细胞系（HeLa、LS174 和 A549）的体外细胞毒活性。所有合成的化合物均显示出显着的抗微生物活性并表达对测试癌细胞系的细胞毒活性，但它们对正常细胞系（MRC5）没有显着影响。丁基衍生物对 HeLa 细胞的活性最强（IC50 = 8.63 μm），而苄基衍生物对 LS174 和 A549 细胞系具有活性（IC50 分别为 10.17 和 12.15 μm）。

  DOI：

  10.1002/cbdv.201700077
• 作为产物：
  描述：

  4-(4-羟基-3-甲氧苯基)-3-丁烯-2-酮 、 1-溴代异戊烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以23%的产率得到(E)-4-[3-methoxy-4-(3-methylbutoxy)phenyl]but-3-en-2-one
  参考文献：
  名称：

  Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents

  摘要：

  Twenty-eight compounds related to dehydrozingerone ( 1), isoeugenol ( 3), and 2-hydroxychalcone ( 4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR ( a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 mu g/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 mu g/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 mu g/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.

  DOI：

  10.1021/np060252z

文献信息

• Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents
  作者：Jin Tatsuzaki、Kenneth F. Bastow、Kyoko Nakagawa-Goto、Seiko Nakamura、Hideji Itokawa、Kuo-Hsiung Lee

  DOI：10.1021/np060252z

  日期：2006.10.1

  Twenty-eight compounds related to dehydrozingerone ( 1), isoeugenol ( 3), and 2-hydroxychalcone ( 4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR ( a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 mu g/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 mu g/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 mu g/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.
• Cytotoxic and Antimicrobial Activity of Dehydrozingerone based Cyclopropyl Derivatives
  作者：Adrijana Z. Burmudžija、Jovana M. Muškinja、Marijana M. Kosanić、Branislav R. Ranković、Slađana B. Novaković、Snežana B. Đorđević、Tatjana P. Stanojković、Dejan D. Baskić、Zoran R. Ratković

  DOI：10.1002/cbdv.201700077

  日期：2017.8

  (4‐(4‐hydroxy‐3‐methoxyphenyl)‐3‐buten‐2‐one) and its O‐alkyl derivatives. Their microbiological activities toward some strains of bacteria and fungi were tested, as well as their in vitro cytotoxic activity against some cancer cell lines (HeLa, LS174 and A549). All synthesized compounds showed significant antimicrobial activity and expressed cytotoxic activity against tested carcinoma cell lines, but they showed

  以脱氢姜酮（4-（4-羟基-3-甲氧基苯基）-3-丁烯-2-酮）及其O为原料，制备了一系列1-乙酰基-2-（4-烷氧基-3-甲氧基苯基）环丙烷-烷基衍生物。测试了它们对某些细菌和真菌菌株的微生物活性，以及​​它们对某些癌细胞系（HeLa、LS174 和 A549）的体外细胞毒活性。所有合成的化合物均显示出显着的抗微生物活性并表达对测试癌细胞系的细胞毒活性，但它们对正常细胞系（MRC5）没有显着影响。丁基衍生物对 HeLa 细胞的活性最强（IC50 = 8.63 μm），而苄基衍生物对 LS174 和 A549 细胞系具有活性（IC50 分别为 10.17 和 12.15 μm）。