nitromalonic aldehyde | 40824-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: nitromalonic aldehyde
• 英文别名: nitromalonaldehyde enol tautomer；3-hydroxy-2-nitro-propenal；3-hydroxy-2-nitro-acrylaldehyde；3-Hydroxy-2-nitro-acrylaldehyd；β-Nitro-α.γ-dioxo-propan；2-Nitro-propandial；1,3-Dioxopropan-2-ylideneazinic acid；3-hydroxy-2-nitroprop-2-enal
• CAS: 40824-82-6
• 化学式: C₃H₃NO₄
• 分子量: 117.061
• InChiKey: JBBHDCMVSJADCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  nitromalonic aldehyde 在 氨 作用下， 以 乙醚 为溶剂， 生成 α-Nitro-β-aminoacrolein
  参考文献：
  名称：

  Kvitko,S.M. et al., Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 477 - 483

  摘要：

  DOI：
• 作为产物：
  描述：

  糠氯酸 在 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 以12%的产率得到nitromalonic aldehyde
  参考文献：
  名称：

  Design, synthesis, DNA-binding and cytotoxicity evaluation of new potential combilexines

  摘要：

  Combilexines, compounds in which a DNA intercalator is linked to a minor groove binding component, interact with the DNA in a sequence specific manner to yield in most cases compounds with anticancer activity. A series of new compounds closely related to netropsin in which the two components were linked by an amide group was synthesised as potential combilexines. As some of these compounds showed cytotoxic activity in vitro, an attempt was made to rationalise their mechanism of action. The DNA binding characteristics of the carboxamides were evaluated by thermal denaturation experiments and by ethidium bromide displacement assay. Their ability to inhibit the topoisomerase I was also determined. It was concluded that the new compounds were only weak DNA ligands although able in some cases to inhibit topoisomerase I. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01349-1

文献信息

• Hale; Robertson, American Chemical Journal, 1908, vol. 39, p. 685
  作者：Hale、Robertson

  DOI：——

  日期：——
• Hill, American Chemical Journal, 1900, vol. 24, p. 9
  作者：Hill

  DOI：——

  日期：——
• Hill; Torrey, American Chemical Journal, 1899, vol. 22, p. 109
  作者：Hill、Torrey

  DOI：——

  日期：——
• Hill; Hale, Chemische Berichte, 1900, vol. 33, p. 1241
  作者：Hill、Hale

  DOI：——

  日期：——
• Design, synthesis, DNA-binding and cytotoxicity evaluation of new potential combilexines
  作者：Christian Hotzel、Annalisa Marotto、Ulf Pindur

  DOI：10.1016/s0223-5234(02)01349-1

  日期：2002.5

  Combilexines, compounds in which a DNA intercalator is linked to a minor groove binding component, interact with the DNA in a sequence specific manner to yield in most cases compounds with anticancer activity. A series of new compounds closely related to netropsin in which the two components were linked by an amide group was synthesised as potential combilexines. As some of these compounds showed cytotoxic activity in vitro, an attempt was made to rationalise their mechanism of action. The DNA binding characteristics of the carboxamides were evaluated by thermal denaturation experiments and by ethidium bromide displacement assay. Their ability to inhibit the topoisomerase I was also determined. It was concluded that the new compounds were only weak DNA ligands although able in some cases to inhibit topoisomerase I. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.