5-Nitro-1-prop-2-ynylindole-2,3-dione | 79552-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-Nitro-1-prop-2-ynylindole-2,3-dione
• CAS: 79552-53-7
• 化学式: C₁₁H₆N₂O₄
• mdl: MFCD11147946
• 分子量: 230.18
• InChiKey: JQZKDHUYXBCDQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-Azidoethyl)-5-fluoroindole-2,3-dione 、 5-Nitro-1-prop-2-ynylindole-2,3-dione 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 以64%的产率得到1-{2-[4-(2,3-dioxo-2,3-dihydro-5-nitroindol-1-ylmethyl)-[1,2,3]triazol-1-yl]ethyl}-5-fluoro-1H-indole-2,3-dione
  参考文献：
  名称：

  叠氮化物-炔环加成途中新的1- ħ 1,2,3-三唑系留靛红缀合物的体外细胞毒性评价

  摘要：

  已经合成了1 H -1,2,3-三唑拴系的靛红共轭物，并评估了其对四种人类癌细胞系的细胞毒性。结果表明5a，5c，5e和5n在THP-1细胞系上的效力是5-氟尿嘧啶的两倍，其中5a和5c最活跃，对除Caco-2以外的所有细胞系的IC 50值均<1。活性曲线显示出对异丁环的取代基的依赖性，优选氢，而任一环上的强吸电子氟和硝基取代基均降低了抗癌活性。

  DOI：

  10.1016/j.ejmech.2012.06.057
• 作为产物：
  描述：

  5-硝基靛红 、 3-溴丙炔 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-Nitro-1-prop-2-ynylindole-2,3-dione
  参考文献：
  名称：

  叠氮化物-炔环加成途中新的1- ħ 1,2,3-三唑系留靛红缀合物的体外细胞毒性评价

  摘要：

  已经合成了1 H -1,2,3-三唑拴系的靛红共轭物，并评估了其对四种人类癌细胞系的细胞毒性。结果表明5a，5c，5e和5n在THP-1细胞系上的效力是5-氟尿嘧啶的两倍，其中5a和5c最活跃，对除Caco-2以外的所有细胞系的IC 50值均<1。活性曲线显示出对异丁环的取代基的依赖性，优选氢，而任一环上的强吸电子氟和硝基取代基均降低了抗癌活性。

  DOI：

  10.1016/j.ejmech.2012.06.057

文献信息

• N-Propargylated isatin-Mannich mono- and bis-adducts: Synthesis and preliminary analysis of in vitro activity against Tritrichomonas foetus
  作者：Nisha、Kewal Kumar、Gaurav Bhargava、Kirkwood M. Land、Kai-Hsiang Chang、Reena Arora、Somdutta Sen、Vipan Kumar

  DOI：10.1016/j.ejmech.2014.01.015

  日期：2014.3

  Cu(I)Cl promoted synthesis of N-propargylated-isatin Mannich mono- and bis-adducts with an extension towards the synthesis of N-propargylated-isatin-7-chloroquinoline conjugates was described. The synthesized scaffolds were evaluated for their in vitro activity against the veterinary protozoal pathogen Tritrichomonas foetus and cytotoxicity against human prostate (PC-3) cancer cell line. The preliminary evaluation data revealed the enhancement in the activity profiles with the introduction of 7-chloroquinoline ring with the most active conjugates 7a, 7c and 7d exhibiting an IC50 of 22.2, 11.3 and 24.5 mu M respectively against T. foetus and minimal toxicity against human prostate (PC-3) cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.
• A Convenient Methodology for the N-Alkylation of Isatin Compounds
  作者：Simon J. Garden、José C. Torres、Leonardo E. da Silva、Angelo C. Pinto

  DOI：10.1080/00397919808006872

  日期：1998.5

  A simple, high yielding, methodology for the N-alkylation of substituted isatin derivatives using calcium hydride in DMF is detailed.
• Cu(I)Cl-promoted synthesis of novel N-alkylated isatin analogs with an extension toward isatin-4-aminoquinoline conjugates: in vitro analysis against Trichomonas vaginalis
  作者：Nisha、Richard Tran、Donald Yang、Dominique Hall、Melissa J. Hopper、Lisa A. Wrischnik、Kirkwood M. Land、Vipan Kumar

  DOI：10.1007/s00044-014-1024-y

  日期：2014.10

  Trichomonas vaginalis, the causative agent of trichomonosis, is the most common non-viral sexually transmitted disease. Infection with this protozoan may have serious consequences, especially for women. Currently, 5-nitroimidazole drugs are the treatment of choice for trichomonosis, but the emergence of drug resistant isolates has limited the effectiveness of this therapy. In this context, a library of isatin-mannich adducts and 4-aminoquinoline-isatin mannich conjugates was synthesized following the Cu-promoted Mannich reaction and evaluated for their preliminary in vitro analysis against T. vaginalis at 50 mu M. The preliminary evaluation data revealed that the introduction of 4-aminoquinoline ring enhanced the activity profiles with compounds viz. 6a and 6c exhibiting percentage growth inhibition of 92.13 and 100 %, respectively. Compounds with high levels of potency were further analyzed to determine their IC50 values as well as cytotoxicity profiles against mammalian cells. The most active compound in the synthesized conjugates displayed an IC50 value of 23 mu M against cultured G3 strain in TYM Diamond's media of T. vaginalis and was non-toxic to cultured mammalian HeLa cells at the same concentration.
• ZHUNGIETU G. I.; ZORIN L. M.; PEXTEP M. A., BUL. AKAD. SHTIINTSE RSSMOLD., IZV. AN MOLDSSR. CEP. BIOL. I XIM. N., 198+
  作者：ZHUNGIETU G. I.、 ZORIN L. M.、 PEXTEP M. A.

  DOI：——

  日期：——
• Synthesis and evaluation of N-heteroarylsubstituted triazolosulfonamides as carbonic anhydrase inhibitors
  作者：Ahmet Balci、Mustafa Arslan、Arleta Rifati Nixha、Cigdem Bilen、Adem Ergun、Nahit Gençer

  DOI：10.3109/14756366.2014.940933

  日期：2015.5.4

  A new series of N-heteroarylsubstituted triazolosulfonamide compounds were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase (hCA) I and II were evaluated. Compounds (3 a-k) were prepared by propargylation of N-heteroaryl compounds. Compound 5 was obtained from sulfanilamide and sodium nitrite followed by addition of sodium azide. The products (6 a-k) were synthesized from compounds 3 and 5. The results showed that all the synthesized compounds were inhibited the CA isoenzymes activity. Figure 6a (IC50 = 0.52 mu M for hCA I and 0.34 mu M for hCA II) has the most inhibitory effect among the synthesized compounds.