3-heptylidene-4,6-dimethoxy-3H-isobenzofuran-1-one | 1580003-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 3-heptylidene-4,6-dimethoxy-3H-isobenzofuran-1-one
• 英文别名: 3-Heptylidene-4,6-dimethoxy-2-benzofuran-1-one
• CAS: 1580003-86-6
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: HZBGOSJNMYWUQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  3-heptylidene-4,6-dimethoxy-3H-isobenzofuran-1-one 在 sodium carbonate 作用下， 以 水 为溶剂， 生成 3-heptyl-3-hydroxy-4,6- dimethoxyisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Chemotherapeutic Mechanism of Action of the Synthetic Resorcinolic Methyl 3,5-dimethoxy-2-octanoylbenzoate

  摘要：

  DOI：

  10.1021/acs.chemrestox.3c00269
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸 、 辛酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 3-heptylidene-4,6-dimethoxy-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Chemotherapeutic Mechanism of Action of the Synthetic Resorcinolic Methyl 3,5-dimethoxy-2-octanoylbenzoate

  摘要：

  DOI：

  10.1021/acs.chemrestox.3c00269

文献信息

• A new synthetic resorcinolic lipid 3-Heptyl-3,4,6-trimethoxy-3H-isobenzofuran-1-one: Evaluation of toxicology and ability to potentiate the mutagenic and apoptotic effects of cyclophosphamide
  作者：Stephanie Dynczuki Navarro、Adilson Beatriz、Alisson Meza、João Renato Pesarini、Roberto da Silva Gomes、Caroline Bilhar Karaziack、Andréa Luiza Cunha-Laura、Antônio Carlos Duenhas Monreal、Wanderson Romão、Valdemar Lacerda Júnior、Mariana de Oliveira Mauro、Rodrigo Juliano Oliveira

  DOI：10.1016/j.ejmech.2014.01.057

  日期：2014.3

  Resorcinolic lipids have important biological actions, including anti-carcinogenic activity. Therefore, we evaluated the mutagenic, genotoxic, immunomodulatory and apoptotic potential and the biochemical and histopathological changes caused by the synthetic resorcinolic lipid 3-Heptyl-3,4,6-trimethoxy-3H-isobenzofuran-1-one, (AMS35AA; 10, 20 and 40 mg/kg) alone or in combination with cyclophosphamide (100 mg/kg) in Swiss mice. The results indicated that AMS35AA is not genotoxic or mutagenic and does not alter liver or kidney histology. However, the compound does cause an increase (p < 0.05)in the levels of glutamic-oxaloacetic transaminase and creatinine and in splenic phagocytosis and liver and kidney apoptosis. When combined with cyclophosphamide, AMS35AA caused increased (p < 0.05) mutagenic damage (although the compound had anti-genotoxic activity), splenic phagocytosis, neutropenia and glutamic-oxaloacetic transaminase and creatinine levels (even in the absence of histological damage) and induced liver and kidney apoptosis. We conclude that this resorcinolic lipid may be an important chemotherapy adjuvant that can potentiate mutagenic damage and increase apoptosis caused by cyclophosphamide without causing adverse effects. In addition, the immunomodulatory activity of the compound should be noted, which counters reductions in lymphocyte number, a primary side effect of cyclophosphamide in cancer therapy. (C) 2014 Elsevier Masson SAS. All rights reserved.