2-(3,4,5-trimethoxybenzylidene)cyclopentanone | 135734-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3,4,5-trimethoxybenzylidene)cyclopentanone
• 英文别名: 2-[(3,4,5-trimethoxyphenyl)methylidene]cyclopentan-1-one
• CAS: 135734-97-3
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: JNFOUFBXMZWZEX-UHFFFAOYSA-N

物化性质

• 沸点：
  422.2±45.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4,5-trimethoxybenzylidene)cyclopentanone 在 三乙胺 、 肼 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (4-fluorophenyl)(3-(3,4,5-trimethoxyphenyl)-2,3,5,6-tetrahydrocyclopenta[c]pyrazol-1(4H)-yl)methanone
  参考文献：
  名称：

  Novel antioxidants’ synthesis and their anti-oxidative activity through activating Nrf2 signaling pathway

  摘要：

  Novel structure compounds (WS) containing 3,4,5-trimethoxyphenyl and acyl pyrazole were designed and synthesized based combination principles. Among them, WS13 was screened out to possess desirable anti-oxidative activity in vitro. Cell survival assay and apoptosis experiment in H2O2 induced PC12 cells injury model all showed that its cytoprotection exhibited a concentration-effect manner. WS13 at 10 mu M could remove ROS with equal effiency to edaravone. Further, it clearly activated Nrf2 nuclear translocation and upregulated GCLC mRNA transcription and protein expression in dose-dependent manner, and its cytoprotection was reversed by GCLC protein inhibitor. In total, WS13 with further promotion can serve as Nrf2-GCLC activator in anti-oxidative therapy. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.02.006
• 作为产物：
  描述：

  N-(1-环戊烯基)吗啉 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 2-(3,4,5-trimethoxybenzylidene)cyclopentanone
  参考文献：
  名称：

  含有邻甲氧基苯基的环状 C7 桥联单羰基姜黄素类似物作为潜在抗胃癌药物的设计、合成和评估

  摘要：

  C7 桥接单羰基姜黄素类似物 (MCA) 的毒性与连接酮类型之间的构效关系 (SAR) 尚不清楚。为了追求有效和少...

  DOI：

  10.1080/14756366.2024.2314233

文献信息

• 2-METHYLENE-5-SUBSTITUTED-METHYLENECYCLOPENTANONE DERIVATIVES AND USE THEREOF
  申请人：Zhao Linxiang

  公开号：US20110060054A1

  公开（公告）日：2011-03-10

  The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.

  本发明涉及2-亚甲基-5-取代-亚甲基环戊酮衍生物，其具有公式I的结构，以及这些衍生物的用途。公式I的衍生物作为活性成分，可用于制备治疗和/或预防诸如乳腺癌、肺癌、结肠癌、直肠癌、胃癌、前列腺癌、膀胱癌、子宫癌、胰腺癌和卵巢癌等癌症疾病的药物。本发明的活性化合物可以单独用作抗癌药物，或与一个或多个其他抗肿瘤药物联合使用。可以通过同时、随后或分别给药每个治疗成分来进行联合治疗。
• 一种3,4,5-三甲氧基苯类化合物及其在制备 抗氧化药物中的应用
  申请人：温州医科大学

  公开号：CN107056707B

  公开（公告）日：2019-08-23

  本发明属药物化学领域，具体涉及一种3,4,5‑三甲氧基苯类化合物及其在制备抗氧化药物中的应用，这种新型抗氧化剂3,4,5‑三甲氧基苯类化合物能够激活Nrf2信号通路，上调通路下游相关蛋白GCLC的表达，进而清除胞内自由基ROS，从而对H2O2诱导的PC12细胞损伤起到保护作用。
• PEG-400 assisted synthesis of 2-(R-benzylidene)-5-(R-cinnamylidene)cyclopentanones
  作者：Alexandra Khrustaleva、Sergey Batalin

  DOI：10.1080/00397911.2022.2056056

  日期：2022.3.4

  Abstract The simple and efficient method has been developed for the synthesis of a new type of cross-conjugated system − 2-(R-benzylidene)-5-(R-cinnamylidene)cyclopentanones in PEG-400. The preparation of these compounds by two routes from 2-(R-benzylidene)cyclopentanones and 2-cinnamylidenecyclopentanone was considered.

  摘要 已经开发了一种简单有效的方法，用于在 PEG-400 中合成一种新型的交叉共轭体系 - 2-(R-亚苄基)-5-(R-肉桂亚基)环戊酮。考虑了从2-(R-亚苄基)环戊酮和2-肉桂亚基环戊酮通过两条路线制备这些化合物。
• 2-methylene-5-substituted-methylenecyclopentanone derivatives and use thereof
  申请人：Zhao Linxiang

  公开号：US08415505B2

  公开（公告）日：2013-04-09

  The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.

  本发明涉及公式I的2-亚甲基-5-取代亚甲基环戊酮衍生物及其用途。公式I的衍生物作为活性成分，可用于制备用于治疗和/或预防癌症疾病，如乳腺癌、肺癌、结肠癌、直肠癌、胃癌、前列腺癌、膀胱癌、子宫癌、胰腺癌和卵巢癌的药物。本发明的活性化合物可单独用作抗癌药物，也可与一种或多种其他抗肿瘤药物联合使用。联合治疗可以通过同时、随后或分别给予每种治疗成分来进行。
• Synthesis and photophysical properties of a new type of merocyanine dye based on N-methyl derivatives of 4-aryl-2-(1-hydroxy-4-nitronaphthalen-2-yl)cyclopenta[b]pyridine
  作者：Sergey Batalin

  DOI：10.1016/j.dyepig.2022.110850

  日期：2022.12

  A simple and efficient method for the synthesis of a new type of merocyanine dye based on N-methyl derivatives of 2-(1-hydroxy-4-nitronaphtalen-2-yl)cyclopenta[b]pyridine by the Chichibabin method was discovered. Three ways of obtaining these systems are considered. The tautomerism and fluorescent properties of the synthesized compounds are considered depending on the structure, the polarity of medium

  发现了一种以2-(1-羟基-4-硝基萘-2-基)环戊二烯[ b ]吡啶的N-甲基衍生物为基础的Chichibabin法合成新型部花青染料的简便高效方法。考虑了三种获得这些系统的方法。合成化合物的互变异构和荧光性质取决于结构，在中性条件下和三氟乙酸存在下介质的极性。在中性条件下，所得的环五[ b ]吡啶以几种互变异构形式存在，主要以酮胺形式存在。