4-(2,3,4-trimethoxyphenyl)butanoic acid | 51686-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2,3,4-trimethoxyphenyl)butanoic acid
• CAS: 51686-52-3
• 化学式: C₁₃H₁₈O₅
• mdl: MFCD12078933
• 分子量: 254.283
• InChiKey: JEDKKYZYTPHGSF-UHFFFAOYSA-N

物化性质

• 沸点：
  378.2±37.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,3,4-trimethoxyphenyl)butanoic acid 在 正丁基锂 、 dimethyl sulfide borane 、 三氟化硼乙醚 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 32.75h， 生成 1-(4-methoxyphenyl)-6,7,8-trimethoxytetralin
  参考文献：
  名称：

  仿生合成芳基四氢木脂素的方法

  摘要：

  3-芳基丙基取代的醌-甲基缩酮的BF 3催化环化为芳基四氢化萘提供了温和的仿生途径。报告了产物的1 H-和13 C-NMR谱。

  DOI：

  10.1016/s0040-4020(01)96619-0
• 作为产物：
  描述：

  1,2,3-三甲氧基苯 生成 4-(2,3,4-trimethoxyphenyl)butanoic acid
  参考文献：
  名称：

  仿生合成芳基四氢木脂素的方法

  摘要：

  3-芳基丙基取代的醌-甲基缩酮的BF 3催化环化提供了在温和条件下进行芳基四氢萘仿生的途径。

  DOI：

  10.1016/s0040-4039(00)81480-x

文献信息

• Combretastatin analogs with tubulin binding activity
  申请人：Pinney G. Kevin

  公开号：US20060293394A1

  公开（公告）日：2006-12-28

  Analogs of combretastatin have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin polymerization. Such compounds are excellent clinical candidates for the treatment of cancer in humans. In addition, certain of these ligands, as pro-drugs, may well prove to be tumor selective vascular targeting chemotherapeutic agents or to have vascular targeting activity resulting in the selective prevention and/or destruction of nonmalignant proliferating vasculature.

  已经发现了与康柏他斯汀类似的化合物，它们展示出令人印象深刻的细胞毒性，以及抑制微管聚合的显著能力。这些化合物是治疗人类癌症的优秀临床候选药物。此外，这些配体中的某些作为前药，很可能证明是肿瘤选择性血管靶向化疗药物，或具有血管靶向活性，导致选择性预防和/或破坏非恶性增殖的血管。
• Synthesis, biological evaluation and mechanism study of a class of benzylideneindanone derivatives as novel anticancer agents
  作者：Jinhui Hu、Jun Yan、Jie Chen、Yanqing Pang、Ling Huang、Xingshu Li

  DOI：10.1039/c5md00139k

  日期：——

  Our findings revealed the benzylideneindanone moiety as a new attractive scaffold for mitosis-targeting drug discovery.

  我们的发现揭示了苄亚甲基吲哚酮基团作为一种新的吸引人的骨架，用于有针对性地发现有丝分裂靶向药物。
• Combretastatin Analogs with Tubulin Binding Activity
  申请人：PINNEY Kevin G.

  公开号：US20090075943A1

  公开（公告）日：2009-03-19

  Analogs of combretastatin have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin polymerization. Such compounds are excellent clinical candidates for the treatment of cancer in humans. In addition, certain of these ligands, as pro-drugs, may well prove to be tumor selective vascular targeting chemotherapeutic agents or to have vascular targeting activity resulting in the selective prevention and/or destruction of nonmalignant proliferating vasculature.

  已经发现了类似于合成静癌素的物质，表现出令人印象深刻的细胞毒性，以及抑制微管聚合的显著能力。这些化合物是治疗人类癌症的优秀临床候选药物。此外，其中某些配体作为前药，可能被证明是肿瘤选择性血管靶向化疗药物，或具有靶向血管活性，导致非恶性增生血管的选择性预防和/或破坏。
• Novel conformationally restricted tetracyclic analogs of Δ8-tetrahydrocannabinol
  作者：Atmaram D. Khanolkar、Dai Lu、Pusheng Fan、Xiaoyu Tian、Alexandros Makriyannis

  DOI：10.1016/s0960-894x(99)00355-8

  日期：1999.8

  Novel analogs of (-)-Delta(8)-tetrahydrocannabinol (Delta(8)-THC) in which the conformation of the side chain was restricted by incorporating the first one or two carbons into a six membered ring fused with the aromatic phenolic A ring were synthesized. The affinities of the novel ligands for CB1 and CB2 indicated that the "southbound" chain conformer retained the highest affinity for both receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists
  作者：Remo Kranich、Anke S. Busemann、Daniel Bock、Sabine Schroeter-Maas、Diana Beyer、Bo Heinemann、Michael Meyer、Katrin Schierhorn、Rainer Zahlten、Gerhard Wolff、Ewald M. Aydt

  DOI：10.1021/jm060536g

  日期：2007.3.1

  This report describes the first results of a rational hit-finding strategy to design novel small molecule antiinflammatory drugs targeting selectins, a family of three cellular adhesion molecules. Based on recent progress in understanding of molecular interaction between selectins and their natural ligands as well as progress in clinical development of synthetic antagonists like 1 (bimosiamose, TBC1269), this study was initiated to discover small molecule selectin antagonists with improved pharmacological properties. Considering 1 as template structure, a ligand-based approach followed by focused chemical synthesis has been applied to yield novel synthetic small molecules (MWr < 500) with a trihydroxybenzene motif, bearing neither peptidic nor glycosidic components, with nanomolar in vitro activity. Biological evaluation involves two kinds of in vitro assays, a static molecular binding assay, and a dynamic HL-60 cell attachment assay. As compared to controls, the novel compounds showed improved biological in vitro activity both under static and dynamic conditions.