3,4-(difluoromethylenedioxy)-6-nitrobenzaldehyde | 294619-51-5

• 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: 3,4-(difluoromethylenedioxy)-6-nitrobenzaldehyde
• 英文别名: 2,2-difluoro-6-nitrobenzo[d][1,3]dioxole-5-carbaldehyde；2,2-difluoro-6-nitrobenz[d][1,3]dioxole-5-carboxaldehyde；2,2-Difluoro-6-nitro-1,3-benzodioxole-5-carbaldehyde
• CAS: 294619-51-5
• 化学式: C₈H₃F₂NO₅
• 分子量: 231.112
• InChiKey: DRKUKGKBWVPNTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  81.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4-(difluoromethylenedioxy)-6-nitrobenzaldehyde 在 ammonium hydroxide 、 iron(II) sulfate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.08h， 以33.2%的产率得到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
• 作为产物：
  描述：

  2,2-二氟-1,3-苯并二恶茂-5-甲醛 在 硫酸 、 硝酸 作用下， 以89 %的产率得到3,4-(difluoromethylenedioxy)-6-nitrobenzaldehyde
  参考文献：
  名称：

  [EN] TRICYCLIC ARYL DERIVATIVES, AND COMPOSITIONS AND METHODS THEREOF
  [FR] DÉRIVÉS ARYLE TRICYCLIQUES, ET COMPOSITIONS ET PROCÉDÉS ASSOCIÉS

  摘要：

  The invention provides novel tricyclic aryl compounds and derivatives thereof, and pharmaceutical compositions thereof and methods for treating diseases and disorders, such as various types of cancer.

  公开号：

  WO2024026129A2

文献信息

• 20(S)-10,11-二氟亚甲二氧基喜树碱衍生物及其制备方法和应用
  申请人：浙江工业大学

  公开号：CN117777153A

  公开（公告）日：2024-03-29

  本发明属于有机合成和医药技术领域，具体涉及20(S)‑10,11‑二氟亚甲二氧基喜树碱衍生物及其制备方法和应用。该衍生物为具有式(Ⅰ)所示结构的化合物、其立体异构体和药学上可接受的盐形式，本发明提供的新型20(S)‑10,11‑二氟亚甲二氧基喜树碱衍生物可用于制备合成预防或治疗肿瘤的喜树碱类药物，该类化合物具有良好的抗炎活性、体内外抗肿瘤活性和细胞跨膜转运能力，且其制备方法易于操作，后处理简便，反应起始原料廉价易得，反应底物可设计性强，反应效率较高，实用性较强。#imgabs0#
• US6268375B1
  申请人：——

  公开号：US6268375B1

  公开（公告）日：2001-07-31
• [EN] TRICYCLIC ARYL DERIVATIVES, AND COMPOSITIONS AND METHODS THEREOF<br/>[FR] DÉRIVÉS ARYLE TRICYCLIQUES, ET COMPOSITIONS ET PROCÉDÉS ASSOCIÉS
  申请人：[en]ENSEM THERAPEUTICS, INC.

  公开号：WO2024026129A2

  公开（公告）日：2024-02-01

  The invention provides novel tricyclic aryl compounds and derivatives thereof, and pharmaceutical compositions thereof and methods for treating diseases and disorders, such as various types of cancer.
• 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.