5-Ethenyl-1,3-dihydropyrrol-2-one | 1380571-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 5-Ethenyl-1,3-dihydropyrrol-2-one
• CAS: 1380571-23-2
• 化学式: C₆H₇NO
• 分子量: 109.128
• InChiKey: BTFFBZHWQNRGOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Ethenyl-1,3-dihydropyrrol-2-one 、 4-苯基氨基脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以76%的产率得到N-phenyl-2-(5-vinyl-1,3-dihydro-2H-pyrrol-2-ylidene)hydrazine-1-carboxamide
  参考文献：
  名称：

  Microwave-assisted Synthesis and Bioevaluation of Some Semicarbazones

  摘要：

  In continuation to our efforts in finding potential therapeutic agents, a variety of biologically significant semicarbazones were synthesized by the reaction of different carbonyl compounds with phenyl semicarbazides through microwave irradiation. Initially, 18 semicarbazones were studied for their antimicrobial, antitumor, and antioxidant potential. None of the tested compounds showed any antibacterial activity; however, some compounds showed significant antifungal activity. Interestingly, all compounds showed antitumor activity when tested against tumors grown on potato discs. These compounds were also tested for their effect on OH radical‐induced oxidative DNA damage. All the compounds showed DNA protection to varying extent. Based on the promising results of antitumor and antioxidant activities, another set of 24 semicarbazones was synthesized, and all of these semicarbazones were evaluated for their antioxidant potential. The results showed that the semicarbazones derived from 2‐nitrobenzaldehyde and acetophenone were the most active 2,2‐diphenyl‐1‐picrylhydrazyl 9 (DPPH) free radical scavengers. The overall results have led to the identification of some interesting compounds which seem to have great potential to be developed into effective anticancer drugs.

  DOI：

  10.1111/j.1747-0285.2012.01360.x

文献信息

• Verfahren zur Herstellung von substituierten Lactamen
  申请人：BASF Aktiengesellschaft

  公开号：EP0293740A2

  公开（公告）日：1988-12-07

  Herstellung von substituierten Lactamen Ia bis Ic (n = 0-2; X = -O-CO-R¹, -O-SO₂-R¹, -CO-R², -CO-O-R², -CO-NR³R⁴; R¹ = C₁-C₈-Rest einer Carbon- bzw. Sulfonsäure; R² = C₁-C₈-Alkyl; R³, R⁴ = H, C₁-C₄-Alkyl oder gemeinsam ein 5- oder 6-gliedriger Ring) durch Umsetzung von Lactamen II mit Vinylverbindungen III CH₂=CH-X und einer radikalbildenden Verbindung IV zu Ia und Herstellung von Ib durch Hydrolyse von solchen Verbindungen Ia, in der X für (-O-CO-R¹) oder (-O-SO₂-R¹) steht, und Herstellung von Ic durch Thermolyse von Ib oder solchen Verbindungen Ia, in denen X (-O-CO-R¹) oder (-O-SO₂-R¹) bedeutet, sowie die neuen substituierten Lactame Ia und Ib mit X = (-O-CO-R¹)- und (-O-SO₂-R¹).

  制备取代的内酰胺 Ia 至 Ic (n = 0-2; X = -O-CO-R¹, -O-SO₂-R¹, -CO-R², -CO-O-R², -CO-NR³R⁴; R¹ = 碳酸或磺酸的 C₁-C₈ 残基；R² = C₁-C₈ 烷基；R³, R⁴ = H, H磺酸；R² = C₁-C₈-烷基；R³、R⁴ = H、C₁-C₄-烷基或合起来是一个 5 或 6 元环）通过内酰胺 II 与乙烯基化合物 III CH₂=CH-X 和自由基形成化合物 IV 反应得到 Ia，通过水解 X 为 (-O-CO-R¹) 或 (-O-SO₂-R¹) 的此类化合物 Ia 制备 Ib，通过热分解 Ib 或 X 为 (-O-CO-R¹) 或 (-O-SO₂-R¹) 的此类化合物 Ia 制备 Ic，以及 X = (-O-CO-R¹)- 和 (-O-SO₂-R¹) 的新取代内酰胺 Ia 和 Ib。
• US4874865A
  申请人：——

  公开号：US4874865A

  公开（公告）日：1989-10-17
• Microwave-assisted Synthesis and Bioevaluation of Some Semicarbazones
  作者：Laila Jafri、Farzana L. Ansari、Maryam Jamil、Saima Kalsoom、Sana Qureishi、Bushra Mirza

  DOI：10.1111/j.1747-0285.2012.01360.x

  日期：2012.6

  In continuation to our efforts in finding potential therapeutic agents, a variety of biologically significant semicarbazones were synthesized by the reaction of different carbonyl compounds with phenyl semicarbazides through microwave irradiation. Initially, 18 semicarbazones were studied for their antimicrobial, antitumor, and antioxidant potential. None of the tested compounds showed any antibacterial activity; however, some compounds showed significant antifungal activity. Interestingly, all compounds showed antitumor activity when tested against tumors grown on potato discs. These compounds were also tested for their effect on OH radical‐induced oxidative DNA damage. All the compounds showed DNA protection to varying extent. Based on the promising results of antitumor and antioxidant activities, another set of 24 semicarbazones was synthesized, and all of these semicarbazones were evaluated for their antioxidant potential. The results showed that the semicarbazones derived from 2‐nitrobenzaldehyde and acetophenone were the most active 2,2‐diphenyl‐1‐picrylhydrazyl 9 (DPPH) free radical scavengers. The overall results have led to the identification of some interesting compounds which seem to have great potential to be developed into effective anticancer drugs.