6-amino-3,4-(difluoromethylenedioxy)benzaldehyde | 294619-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-amino-3,4-(difluoromethylenedioxy)benzaldehyde
• 英文别名: 6-amino-2,2-difluorobenzo[d][1,3]dioxolane-5-carbaldehyde；6-Amino-2,2-difluorobenzo[d][1,3]dioxole-5-carbaldehyde；6-amino-2,2-difluoro-1,3-benzodioxole-5-carbaldehyde
• CAS: 294619-52-6
• 化学式: C₈H₅F₂NO₃
• 分子量: 201.129
• InChiKey: NHIGHALJCADISO-UHFFFAOYSA-N

物化性质

• 沸点：
  289.0±40.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-amino-3,4-(difluoromethylenedioxy)benzaldehyde 在 吗啉 、 吡啶 作用下， 反应 13.0h， 生成 ethyl 7-amino-2,2-difluoro-[1,3]dioxolano[4,5-g]quinoline-6-carboxylate
  参考文献：
  名称：

  [EN] TRICYCLIC COMPOUND, PREPARATION METHOD THEREFOR AND MEDICAL USE THEREOF
  [FR] COMPOSÉ TRICYCLIQUE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION MÉDICALE
  [ZH] 三环化合物及其制备方法和医药用途

  摘要：

  一种三环化合物及其制备方法和医药用途。特别地，涉及通式(I)所示的化合物，含有其的药物组合物，及其制备方法和在用于预防和/或治疗由毒性醛引发的多种疾病中的应用。其中通式(I)中的各基团的定义与说明书中的定义相同。

  公开号：

  WO2022267930A1
• 作为产物：
  描述：

  2,2-二氟-1,3-苯并二恶茂-5-甲醛 在 ammonium hydroxide 、 硝酸 、 iron(II) sulfate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 2.08h， 生成 6-amino-3,4-(difluoromethylenedioxy)benzaldehyde
  参考文献：
  名称：

  Analysis of stereoelectronic properties of camptothecin analogues in relation to biological activity

  摘要：

  Camptothecin and four of its 10,11-methylenedioxy analogues were examined for their activity against the pathogenic protozoan Leishmania donovani in vitro. The methylenedioxy analogues were 36- to 180-fold more potent than the parent camptothecin, possessing IC50 values ranging from 160 to 32 nM against the parasite. Our finding that the methylenedioxy camptothecins possess greater activity than camptothecin, which is also the case for other cell types and for the generation of cleavable complex in the presence of DNA and purified mammalian topoisomerase I, prompted us to examine the molecular features of camptothecin and methylenedioxy camptothecin analogues. A delocalization of positive potential was observed in the methylenedioxy camptothecin analogues, which could increase the affinity of these molecules for DNA. In addition, geometrical and electronic differences between the E ring of camptothecin and its methylenedioxy analogues were noted. One or both of these factors may contribute to the superior biological activity of the methylenedioxy camptothecin analogues. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(00)00111-5

文献信息

• Camptothecin analogs having an E-ring ketone
  申请人：Research Triangle Institute

  公开号：US20040266804A1

  公开（公告）日：2004-12-30

  Camptothecin analogs having an E-ring ketone are effective anti tumor compounds. These compounds inhibit the enzyme topoisomerase I and may alkylate DNA of the associated topoisomerase I DNA cleavable complex.

  拥有E环酮基团的紫杉醇类似物是有效的抗肿瘤化合物。这些化合物抑制酶拓扑异构酶I，并可能烷化与拓扑异构酶I DNA可切割复合物相关的DNA。
• Analysis of stereoelectronic properties of camptothecin analogues in relation to biological activity
  作者：Karl A. Werbovetz、Apurba K. Bhattacharjee、James J. Brendle、John P. Scovill

  DOI：10.1016/s0968-0896(00)00111-5

  日期：2000.7

  Camptothecin and four of its 10,11-methylenedioxy analogues were examined for their activity against the pathogenic protozoan Leishmania donovani in vitro. The methylenedioxy analogues were 36- to 180-fold more potent than the parent camptothecin, possessing IC50 values ranging from 160 to 32 nM against the parasite. Our finding that the methylenedioxy camptothecins possess greater activity than camptothecin, which is also the case for other cell types and for the generation of cleavable complex in the presence of DNA and purified mammalian topoisomerase I, prompted us to examine the molecular features of camptothecin and methylenedioxy camptothecin analogues. A delocalization of positive potential was observed in the methylenedioxy camptothecin analogues, which could increase the affinity of these molecules for DNA. In addition, geometrical and electronic differences between the E ring of camptothecin and its methylenedioxy analogues were noted. One or both of these factors may contribute to the superior biological activity of the methylenedioxy camptothecin analogues. Published by Elsevier Science Ltd.
• [EN] TRICYCLIC COMPOUND, PREPARATION METHOD THEREFOR AND MEDICAL USE THEREOF<br/>[FR] COMPOSÉ TRICYCLIQUE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION MÉDICALE<br/>[ZH] 三环化合物及其制备方法和医药用途
  申请人：THE NAT INSTITUTES OF PHARMACEUTICAL R&D CO LTD

  公开号：WO2022267930A1

  公开（公告）日：2022-12-29

  一种三环化合物及其制备方法和医药用途。特别地，涉及通式(I)所示的化合物，含有其的药物组合物，及其制备方法和在用于预防和/或治疗由毒性醛引发的多种疾病中的应用。其中通式(I)中的各基团的定义与说明书中的定义相同。