2-(5-(morpholinosulfonyl)-2-oxoindolin-3-ylidene) malononitrile | 854948-85-9

• 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: 2-(5-(morpholinosulfonyl)-2-oxoindolin-3-ylidene) malononitrile
• 英文别名: 2-(5-morpholin-4-ylsulfonyl-2-oxo-1H-indol-3-ylidene)propanedinitrile
• CAS: 854948-85-9
• 化学式: C₁₅H₁₂N₄O₄S
• 分子量: 344.351
• InChiKey: VJGWYJOZJWNUBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(5-(morpholinosulfonyl)-2-oxoindolin-3-ylidene) malononitrile 在 盐酸 、 溶剂黄146 作用下， 反应 12.0h， 以43%的产率得到6-(morpholine-4-sulfonyl)-2-oxo-1,2-dihydro-3,4-quinolinedicarboxylic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of 4-Substituted 2-(2-Acetyloxyethyl)-8-(morpholine- 4-sulfonyl)pyrrolo[3,4-c]quinoline- 1,3-diones as Potent Caspase-3 Inhibitors

  摘要：

  Synthesis, biological evaluation, and SAR dependencies for a series of novel 1,3-dioxo-2,3-dihydro-1H-pyrrolo-[3,4-c]quinoline inhibitors of caspase-3 are described. The inhibitory activity of the synthesized compounds is highly dependent on the nature of 4-substituents on the core scaffold. 4-Methyl-and 4-phenyl-substituted derivatives, which were the most active compounds within this series, inhibited caspase-3 with IC50 of 23 and 27 nM, respectively.

  DOI：

  10.1021/jm048987t
• 作为产物：
  描述：

  3,3-dichloro-5-(morpholin-4-ylsulfonyl)-1,3-dihydro-2H-indol-2-one 在 N-甲基吗啉 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-(5-(morpholinosulfonyl)-2-oxoindolin-3-ylidene) malononitrile
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of 4-Substituted 2-(2-Acetyloxyethyl)-8-(morpholine- 4-sulfonyl)pyrrolo[3,4-c]quinoline- 1,3-diones as Potent Caspase-3 Inhibitors

  摘要：

  Synthesis, biological evaluation, and SAR dependencies for a series of novel 1,3-dioxo-2,3-dihydro-1H-pyrrolo-[3,4-c]quinoline inhibitors of caspase-3 are described. The inhibitory activity of the synthesized compounds is highly dependent on the nature of 4-substituents on the core scaffold. 4-Methyl-and 4-phenyl-substituted derivatives, which were the most active compounds within this series, inhibited caspase-3 with IC50 of 23 and 27 nM, respectively.

  DOI：

  10.1021/jm048987t

文献信息

• Design, synthesis, molecular docking and biological activity evaluation of some novel indole derivatives as potent anticancer active agents and apoptosis inducers
  作者：Ahmed M. Sh. El-Sharief、Yousry A. Ammar、Amany Belal、Marwa A.M. Sh. El-Sharief、Yehia A. Mohamed、Ahmed B.M. Mehany、Gameel A.M. Elhag Ali、Ahmed Ragab

  DOI：10.1016/j.bioorg.2019.01.016

  日期：2019.4

  13C NMR and elemental analysis. Anticancer activity against three cancer cell lines (HepG-2, HCT-116 and MCF-7) were evaluated using sulforhodamine B assay method. Compounds 4b, 4c, 7a, 7c and 9 showed broad spectrum anticancer activity on the three tested cell lines with IC50 values less than 10 µM. Cell cycle analysis was performed for the most promising derivatives, compounds 4b and 7c arrested HepG-2

  5-吗啉代磺酰赖氨酸（1）与苯乙酮（2a-e）反应，得到3-羟基-3-取代的-2-氧代吲哚3a-e，当用乙酸处理时，预期的3-苯乙叉基-2-氧代吲哚4a-d和4得到-羟基-5'-（吗啉磺酰基）螺[色烯-2，3'-吲哚啉] -2'-一6。将Isatin衍生物（1）与氰基衍生物搅拌，生成芳基化合物（7a-c），同时在回流条件下，得到吡咯并[2,3-b]吲哚（8，9）。此外，伊斯丹（1）在丙二腈的存在下与吡唑并-5-酮或3-取代的苯酚反应，得到螺并吲哚衍生物（10a，b）和（11a，b）。另外，通过将（7a）与吡唑并-5-酮或3-取代的苯酚环合而获得化合物（10a，b）和（11a，b）。通过IR，1 H NMR，13 C NMR和元素分析鉴定所获得的化合物。使用磺基罗丹明B测定法评估了对三种癌细胞系（HepG-2，HCT-116和MCF-7）的抗癌活性。化合物4b，4c，7a，7c和9对三种测试
• One-pot synthesis and molecular docking of some new spiropyranindol-2-one derivatives as immunomodulatory agents and in vitro antimicrobial potential with DNA gyrase inhibitor
  作者：Mohamed A. Salem、Ahmed Ragab、Ahmed A. Askar、Abeer El-Khalafawy、Abeer H. Makhlouf

  DOI：10.1016/j.ejmech.2019.111977

  日期：2020.2

  a series of 2-oxospiro[indoline-3,4'-pyran]derivatives 4 and 7 were obtained in good yield under mild conditions from the one-pot reaction of indole-2,3-dione derivatives 1, appropriate methylene active nitriles 2 and β-dicarbonyl compound 3 or 6. The newly synthesized compounds were characterized and evaluated for their in vitro antibacterial, antifungal as well as immunomodulatory activity. According

  从吲哚-2,3-二酮衍生物1，合适的亚甲基活性腈2的单锅反应中，在温和条件下以高收率获得了一系列2-oxospiro [indoline-3,4'-pyran]衍生物4和7。以及β-二羰基化合物3或6。对新合成的化合物进行了表征，并对其体外抗菌，抗真菌和免疫调节活性进行了评估。根据MIC值，评估了最有效的化合物4f，4h，7a，7c，7e，7f，7g，8a和8c的MBC并显示出很高的杀灭病原体活性，对诺氟沙星具有良好的MBC值，并对其进行了研究扩展的多药耐药菌（MDRB）面板并显示出有希望的中度多药耐药活性，化合物7f的效果比诺氟沙星好得多，并具有更高的效价结果。此外，最有效的化合物显示嗜中性粒细胞的细胞内杀伤活性增加，这证实了其免疫刺激能力。9种活性化合物中的8种对金黄色葡萄球菌DNA促旋酶的抑制活性比环丙沙星（26.43±0.64μM）强（IC.50）在（18.07±0.18）至（27
• Synthesis and Structure−Activity Relationship of 4-Substituted 2-(2-Acetyloxyethyl)-8-(morpholine- 4-sulfonyl)pyrrolo[3,4-<i>c</i>]quinoline- 1,3-diones as Potent Caspase-3 Inhibitors
  作者：Dmitri V. Kravchenko、Yulia A. Kuzovkova、Volodymyr M. Kysil、Sergey E. Tkachenko、Sergey Maliarchouk、Ilya M. Okun、Konstantin V. Balakin、Alexandre V. Ivachtchenko

  DOI：10.1021/jm048987t

  日期：2005.6.1

  Synthesis, biological evaluation, and SAR dependencies for a series of novel 1,3-dioxo-2,3-dihydro-1H-pyrrolo-[3,4-c]quinoline inhibitors of caspase-3 are described. The inhibitory activity of the synthesized compounds is highly dependent on the nature of 4-substituents on the core scaffold. 4-Methyl-and 4-phenyl-substituted derivatives, which were the most active compounds within this series, inhibited caspase-3 with IC50 of 23 and 27 nM, respectively.