7-methoxy-4-(3,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene | 360796-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methoxy-4-(3,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene
• 英文别名: Naphthalene, 1,2-dihydro-7-methoxy-4-(3,4,5-trimethoxyphenyl)-
• CAS: 360796-28-7
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: AJLOACGRKIDXFU-UHFFFAOYSA-N

物化性质

• 沸点：
  458.4±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-4-(3,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到6-methoxy-1-(3,4,5-trimethoxyphenyl)naphthalene
  参考文献：
  名称：

  Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: Synthesis, cytotoxicity and antitubulin activity

  摘要：

  A novel series of dihydronaphtalene, tetrahydronaphtalene and naphtalene derivatives as restricted analogues of isoCA-4 were designed, synthesized and evaluated for their anticancer properties. High cell growth inhibition against four tumour cell lines was observed at a nanomolar level with dihydronaphtalenes 1d, e and 1h, tetrahydronaphtalene 2c and naphtalene 3c. Structure activity relationships are also considered. These compounds exhibited a significant inhibitory activity toward tubulin polymerization (IC50 = 2-3 mu M), comparable to that of isoCA-4. The effect of the lead compounds le and 2c on the cancer cells tested was associated with cell cycle arrest in the G(2)/M phase. Docking studies reveal that these compounds showed a binding mode similar to those observed with their non-constraint isoCA-4 and isoerianin congeners. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.001
• 作为产物：
  描述：

  5-碘-1,2,3-三甲氧基苯 、 N'-(6-methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)-4-methylbenzenesulfonohydrazide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium tert-butoxide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.0h， 以75%的产率得到7-methoxy-4-(3,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene
  参考文献：
  名称：

  Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: Synthesis, cytotoxicity and antitubulin activity

  摘要：

  A novel series of dihydronaphtalene, tetrahydronaphtalene and naphtalene derivatives as restricted analogues of isoCA-4 were designed, synthesized and evaluated for their anticancer properties. High cell growth inhibition against four tumour cell lines was observed at a nanomolar level with dihydronaphtalenes 1d, e and 1h, tetrahydronaphtalene 2c and naphtalene 3c. Structure activity relationships are also considered. These compounds exhibited a significant inhibitory activity toward tubulin polymerization (IC50 = 2-3 mu M), comparable to that of isoCA-4. The effect of the lead compounds le and 2c on the cancer cells tested was associated with cell cycle arrest in the G(2)/M phase. Docking studies reveal that these compounds showed a binding mode similar to those observed with their non-constraint isoCA-4 and isoerianin congeners. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.001

文献信息

• TUBULIN BINDING LIGANDS AND CORRESPONDING PRODRUG CONSTRUCTS
  申请人：BAYLOR UNIVERSITY

  公开号：EP1263763A2

  公开（公告）日：2002-12-11
• TUBULIN BINDING LIGANDS
  申请人：BAYLOR UNIVERSITY

  公开号：EP1263763B1

  公开（公告）日：2007-07-25
• BENZOSUBERENE ANALOGUES AND RELATED COMPOUNDS WITH ACTIVITY AS ANTICANCER AGENTS
  申请人：Baylor University

  公开号：EP3836910A1

  公开（公告）日：2021-06-23
• [EN] TUBULIN BINDING LIGANDS AND CORRESPONDING PRODRUG CONSTRUCTS<br/>[FR] LIGANDS DE LIAISON DE TUBULINE ET CONSTRUCTIONS CORRESPONDANTES DE PROMEDICAMENTS
  申请人：UNIV BAYLOR

  公开号：WO2001068654A2

  公开（公告）日：2001-09-20

  A diverse set of tubulin binding ligands have been discovered which are structural by characterized, in a general sense, by a semi-rigid molecular framework capable of maintaining aryl-aryl, pseudo pi stacking distances appropriate for molecular recognition of tubulin. In phenolic or amino form, these ligands may be further functionalized to prepare phosphate esters, phosphate salts, and phosphoramides capable of demonstrating selective targeting and destruction of tumor cell vasculature.
• [EN] BENZOSUBERENE ANALOGUES AND RELATED COMPOUNDS WITH ACTIVITY AS ANTICANCER AGENTS<br/>[FR] ANALOGUES DE BENZOSUBERÈNE ET COMPOSÉS APPARENTÉS AYANT UNE ACTIVITÉ EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：UNIV BAYLOR

  公开号：WO2020037209A1

  公开（公告）日：2020-02-20

  A series of benzosuberene analogues demonstrate effective inhibition of tubulin polymerization, cytotoxicity against human cancer cell lines, and vascular dismption in tumors.