1-(5-methyl-2-oxoindolin-3-ylidene)semicarbazide | 194164-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(5-methyl-2-oxoindolin-3-ylidene)semicarbazide
• 英文别名: [(5-methyl-2-oxoindol-3-yl)amino]urea
• CAS: 194164-32-4
• 化学式: C₁₀H₁₀N₄O₂
• mdl: MFCD00565734
• 分子量: 218.215
• InChiKey: YXMRJNXDLIXNEM-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C
• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  100.07
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  肉桂酸 、 1-(5-methyl-2-oxoindolin-3-ylidene)semicarbazide 在 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 以57 %的产率得到2-((Z)-5-methyl-2-oxoindol-3-ylidene)-N-cinnamohydrazide-1-carboxamide
  参考文献：
  名称：

  Design and synthesis optimization of novel diimide indoles derivatives for ameliorating acute lung injury through modulation of NF-κB signaling pathway

  摘要：

  DOI：

  10.1016/j.bioorg.2023.106557
• 作为产物：
  描述：

  4-甲基苯胺盐酸盐 在 硫酸 、 盐酸羟胺 、 sodium acetate 、 sodium sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 10.17h， 生成 1-(5-methyl-2-oxoindolin-3-ylidene)semicarbazide
  参考文献：
  名称：

  Gupta, Neeti; Singh, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1998, vol. 37, # 1, p. 75 - 79

  摘要：

  DOI：

文献信息

• Synthesis and antibacterial activity of Schiff bases of 5-substituted isatins
  作者：Kamaleddin Haj Mohammad Ebrahim Tehrani、Maryam Hashemi、Maryam Hassan、Farzad Kobarfard、Shohreh Mohebbi

  DOI：10.1016/j.cclet.2015.10.027

  日期：2016.2

  Abstract Based on the existing reports on the bioactive isatin derivatives, a number of Schiff bases were synthesized by reacting 5-substituted isatins with bioactive amines/hydrazides and their structures were confirmed using spectroscopic methods such as NMR, IR and mass spectrometry. Furthermore, N -benzylation of isatin followed by the Schiff base formation furnished a new series of compounds (

  摘要根据已有的有关生物活性靛红衍生物的报道，通过5-取代的靛红与生物活性胺/酰肼的反应合成了许多席夫碱，并通过核磁共振，红外光谱和质谱等方法证实了其结构。此外，通过对Isatin进行N-苄基化和随后形成Schiff碱，提供了一系列新化合物（11a-13c），该化合物可以分析Isatin N-取代对所得化合物生物活性的影响。使用微量滴定板法对一系列革兰氏阳性和革兰氏阴性细菌菌株评估了合成衍生物的抗菌活性。化合物2d，3b，5c和6a是针对铜绿假单胞菌的最有效衍生物（MIC = 6.25μg/ mL）。对结构-活性关系的分析表明，掺入基于（硫）脲的席夫碱可产生更有效的衍生物，并具有更广泛的抗菌活性。此外，高度亲脂性化合物（如11a-12c）未显示任何可测量的抗菌活性，这意味着最佳的亲脂性可能是所研究的isatins抗菌活性的重要要求。最后，发现N-苄基异丁香酮的乙内酰脲衍生物（13a-13c）
• Investigation of Reactions Between Binucleophilic Reagents with 2-(2-Oxindolin-3-ylidene)malononitrile Derivatives
  作者：Mohammad Seifi、Hassan Sheibani

  DOI：10.2174/1570178611310070004

  日期：2013.7.1

  Nucleophilic addition of hydrazines and thiosemicarbazide to the 2-(2-oxoindolin-3-ylidene) malononitrile derivatives 1, followed by elimination of malononitrile, lead to 3-(2-arylhydrazono)indolin-2-ones and 1-(2-oxoindolin-3- ylidene)thiosemicarbzides respectively. Also the reaction of compounds 1 with 4-substituted thiosemicarbazides, followed by elimination and cyclization, afforded spiro(indolone-3,2´-[1,3,4]thiadiazol)-2-ones. So all of these nucleophilic reactions with isatin and substituted isatins released the same products.

  将肼和硫代半缩氨基脲对2-(2-氧代吲哚啉-3-亚基)丙二腈衍生物1进行亲核加成后，脱除丙二腈，分别得到3-(2-芳基亚肼基)吲哚啉-2-酮和1-(2-氧代吲哚啉-3-亚基)硫代半缩氨基脲。同样地，化合物1与4-取代的硫代半缩氨基脲反应后，经过消除和环化，生成螺(吲哚酮-3,2'-[1,3,4]噻二唑)-2-酮。综上所述，这些对靛红和取代靛红的亲核反应都得到了相同的产物。
• One‐pot multicomponent synthesis of novel 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe ₃ O ₄ MNPs as highly effective nanocatalyst
  作者：Zohreh Esam、Malihe Akhavan、Ahmadreza Bekhradnia

  DOI：10.1002/aoc.6005

  日期：2021.1

  (DLS), Brunauer–Emmett–Teller (BET), and vibrating sample magnetometer (VSM) techniques. It was applied as an efficient and reusable catalyst for the synthesis of 2‐(piperazin‐1‐yl) quinoxaline and benzimidazole derivatives via a one‐pot multiple‐component cascade reaction under green conditions. The results displayed the excellent catalytic activity of Fe3O4@PFBA–metformin@SO3H as an organic–inorganic

  已经成功地报道了将磺酸固定在Fe 3 O 4磁性纳米颗粒（MNPs）表面上作为新型酸纳米催化剂。制备的超顺磁性核-壳（Fe 3 O 4 @ PFBA-Metformin @ SO 3的形态特征，热稳定性，磁性和其他物理化学性质H）使用傅里叶变换红外（FTIR），X射线衍射（XRD），能量色散X射线光谱（EDS），场发射扫描电子显微镜（FESEM），透射电子显微镜（TEM），热重分析–差示热分析（TGA-DTA），原子力显微镜（AFM），动态光散射（DLS），布鲁诺尔-埃米特-泰勒（BET）和振动样品磁力计（VSM）技术。它是在绿色条件下通过单锅多组分级联反应合成2-（哌嗪-1-基）喹喔啉和苯并咪唑衍生物的一种有效且可重复使用的催化剂。结果表明，Fe 3 O 4 @ PFBA–metformin @ SO 3具有优异的催化活性。H作为有机-无机杂化纳米催化剂，用于缩合和多组分曼尼希型反应。该
• Synthesis and antimycobacterial evaluation of various 7-substituted ciprofloxacin derivatives
  作者：Dharmarajan Sriram、Perumal Yogeeswari、Jafar Sadik Basha、Deshpande R. Radha、Valakunja Nagaraja

  DOI：10.1016/j.bmc.2005.05.063

  日期：2005.10

  Tuberculosis continues to be a major cause of morbidity and mortality all over the world. Various 7-substituted ciprofloxacin derivatives were synthesized and evaluated for antimycobacterial activity in vitro and in vivo against Mycobacterium tuberculosis and for inhibition of the supercoiling activity of DNA gyrase from Mycobacterium smegmatis. Preliminary results indicated that most of the compounds demonstrated better in vitro antimycobacterial activity against M. tuberculosis than ciprofloxacin. Compound 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[[N-4-[1'-(5- methylisatinyl-ss-semicarbazo)]methyl]N'-piperazinyl]-3-quinoline carboxylic acid (3h) decreased the bacterial load in spleen tissue with 0.76-log(10) protections and was considered to be moderately active in reducing bacterial count in spleen. The results demonstrated the potential and importance of developing new quinolone derivatives against mycobacterial infections. (c) 2005 Published by Elsevier Ltd.
• Gatifloxacin derivatives: Synthesis, antimycobacterial activities, and inhibition of Mycobacterium tuberculosis DNA gyrase
  作者：Dharmarajan Sriram、Alexandra Aubry、Perumal Yogeeswari、L.M. Fisher

  DOI：10.1016/j.bmcl.2006.02.065

  日期：2006.6

  Sixteen 7-substituted gatifloxacin derivatives were synthesized and evaluated for antimycobacterial activity in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB), and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. tuberculosis. Among the synthesized compounds, 1-cyclopropyl-6-fluoro-8-methoxy-7-[[[N-4-[I'-(5-isatinyl-beta-semicarbazo)]methyl]3-methyl]N-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (3d) was found to be the most active compound in vitro with an MIC of 0.0125 mu g/mL against MTB and MTR-TB. In the in vivo animal model 3d decreased the bacterial load in lung and spleen tissues with 3.62- and 3.76-log 10 protections, respectively. Compound 3d was also found to be equally active as gatifloxacin in the inhibition of the supercoiling activity of wild-type M. tuberculosis DNA gyrase with an IC50 of 3.0 mu g/mL. The results demonstrate the potential and importance of developing new quinolone derivatives against mycobacterial infections. (c) 2006 Elsevier Ltd. All rights reserved.