3-[(1,3-thiazolidin-4-one-2-yl)hydrazido]-indole-2-one | 22915-25-9

• 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: 3-[(1,3-thiazolidin-4-one-2-yl)hydrazido]-indole-2-one
• 英文别名: 2-[(2-oxoindolin-3-ylidene)hydrazono]thiazolidin-4-one；Thiazolidin-2,4-dion-2-<2',3'-dihydro-2'-indolon-3'-hydrazon>；2-(isatin-3-azino)-4-thiazolidinone；indole-2,3-dione 3-[(4-oxo-thiazolidin-2-ylidene)-hydrazone]；2-[2-(2-oxoindol-3-yl)hydrazinyl]-1,3-thiazol-4-one
• CAS: 22915-25-9
• 化学式: C₁₁H₈N₄O₂S
• mdl: MFCD00655674
• 分子量: 260.276
• InChiKey: AHULYAQAIQPYFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  82.92
• 氢给体数：
  2.0
• 氢受体数：
  5.0

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-[(1,3-thiazolidin-4-one-2-yl)hydrazido]-indole-2-one 在 sodium acetate 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-[(5-(4-chlorobenzylidene)-3-N-ethoxyphthalimido-1,3-thiazolidin-4-one-2-yl)hydrazido]-1-N-ethoxyphthalimidoindole-2-one
  参考文献：
  名称：

  Hussain, Nasir; Joshi, Ajit; Sharma, Chirag, Asian Journal of Chemistry, 2012, vol. 24, # 12, p. 5917 - 5921,5

  摘要：

  DOI：
• 作为产物：
  描述：

  靛红 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 11.0h， 生成 3-[(1,3-thiazolidin-4-one-2-yl)hydrazido]-indole-2-one
  参考文献：
  名称：

  Hussain, Nasir; Joshi, Ajit; Sharma, Chirag, Asian Journal of Chemistry, 2012, vol. 24, # 12, p. 5917 - 5921,5

  摘要：

  DOI：

文献信息

• Microwave-Assisted Synthesis of Some Novel Thiazolidinone and Thiohydantoin Derivatives of Isatins
  作者：Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.1080/10426500903567554

  日期：2010.10.28

  A simple, rapid, and efficient method for the synthesis of some new thiazolidinone and thiohydantoin derivatives of isatins along with some Mannich bases has been achieved in excellent yield from indole-2,3-dione-3-thiosemicarbazone employing microwave irradiation.

  一种简单、快速和有效的方法，用于合成一些新的靛红噻唑烷酮和硫代乙内酰脲衍生物以及一些曼尼希碱，使用微波辐射从 indole-2,3-dione-3-thiosemicarbazone 中获得了极好的收率。
• Synthesis and In Vitro Evaluation of Some Isatin-Thiazolidinone Hybrid Analogues as Anti-Proliferative Agents
  作者：P. K. Ramshid、Sankar Jagadeeshan、Anand Krishnan、Mary Mathew、S. Asha Nair、M. Radhakrishna Pillai

  DOI：10.2174/157340610793358909

  日期：2010.9.1

  A range of isatin-thiazolidinone hybrid analogues were synthesized and their cytotoxicity was evaluated against several cancer cell lines in vitro. The acute toxicity studies in mice models revealed that these analogues possess low systemic toxicity and are safe up to 1600mg/Kg. Among the compounds synthesized, 5-(2-nitrobenzylidene)-2-(isatin-3- azino)-thiazolidin-4-one (CI) has been shown to be the most active, highly promising compound which induced S phase arrest in cell cycle in a time dependent manner. Our initial analysis indicate that incorporation of electron withdrawing group at ortho position of the ring favors over the meta and para positions for eliciting its cytostatic effect. Overall, the in vitro biological evaluation suggests that the growth inhibitory effect of CI is promising and can be studied further.

  一系列靛红-噻唑烷二酮杂化类似物被合成，并在体外对多种癌细胞系进行了细胞毒性评估。在小鼠模型中的急性毒性研究表明，这些类似物的系统毒性较低，安全性高达1600毫克/公斤。在合成的化合物中，5-(2-硝基苯亚甲基)-2-(靛红-3-氮杂)噻唑烷-4-酮（CI）显示为活性最高的化合物，具有高度潜力，能够以时间依赖性方式诱导细胞周期停滞在S期。我们的初步分析表明，在环的邻位引入吸电子基团比间位和对位更有利于发挥其细胞抑制作用。总体而言，体外生物学评估表明，CI的生长抑制效应具有潜力，值得进一步研究。
• Synthesis of novel N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazine derivatives as cyclooxygenase‐2 inhibitors
  作者：Abida Khan、Anupama Diwan、Hamdy K Thabet、Mohd Imran

  DOI：10.1002/ddr.21655

  日期：2020.8

  N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazines as COX‐2 inhibitors have been developed (Supplementary material Appendix 1). The novel aldehyde 3 was prepared by reacting 6‐phenylpyridazin‐3(2H)‐one with 4‐fluorobenzaldehyde. The aldehyde 3 was reacted with different hydrazines and thiazolidin‐4‐ones to obtain the novel N‐substitutedphenyl‐6‐oxo‐3‐phenylpyridazine derivatives. These were assessed for their anti‐inflammatory

  一些新型的非致溃疡性 N-取代苯基-6-氧代-3-苯基哒嗪作为 COX-2 抑制剂被开发出来（补充材料附录 1）。通过 6-苯基哒嗪-3( 2H )-one 与 4-氟苯甲醛反应制备了新型醛3。醛3与不同的肼和噻唑啉-4-酮反应得到新型N-取代苯基-6-氧代-3-苯基哒嗪衍生物。评估了它们的抗炎潜力和胃溃疡形成作用。还进行了分子对接研究。光谱数据与化合物的分配结构一致。化合物4a (IC 50 = 17.45 nm；p < .05)，4b (IC 50 = 17.40 nm; p < .05)、5a (IC 50 = 16.76 nm; p < .05) 和10 (IC 50 = 17.15 nm; p < .05) 比塞来昔布（IC 50 = 17.79 nm；p < .05）。这些发现与4a、4b、5a和10的分子对接研究一致。在体内的抗炎轮廓图4a，图4b，图5a，和10也优于塞来昔
• Synthesis of Some New Spiro, Isolated and Fused Heterocycles Based on 1<i>H</i>-indole-2-One
  作者：T. I. El-Emary、R. A. Ahmed、E. A. Bakhite

  DOI：10.1002/jccs.200100134

  日期：2001.10

  The reaction of 3-benzoylcyanomethylidine-1(H)-indole-2-one (1) with a variety of active methylene compounds, thioglycolic acid, glycine, hydrazine hydrate and phenyl hydrazine led to the formation of compounds 4a-d-10. 3-Thiosemicarbazide-1(H)-indole-2-one 2 on reaction with α-halocarbonyl compounds gave compounds 11a-c, 12a-c. The latter compounds on heating with phosphoryl chloride, cyclization

  3-benzoylcyanomethylidine-1(H)-indole-2-one (1) 与多种活性亚甲基化合物、巯基乙酸、甘氨酸、水合肼和苯肼反应生成化合物 4a-d-10。3-Thiosemicarbazide-1(H)-indole-2-one 2 与 α-卤代羰基化合物反应得到化合物 11a-c、12a-c。后一种化合物在与磷酰氯一起加热时，通过失水发生环化，得到角四环化合物13a、b和14a-c。氰基乙腙衍生物 3 在原甲酸三乙酯中加热后很容易环化，得到三环体系，氧代哒嗪基吲哚 15。另一方面，3 与亚苄基丙二腈和亚苄基乙基氰基乙酸酯的反应得到吡喃基腙衍生物 16a、b。
• Synthesis of Some New Heterocyclic Compounds Derived from 3-Formylchromones and Their Antimicrobial Evaluation
  作者：A. Bari、S. S. Ali、A. Kadi、I. A. Hashmi、S. W. Ng

  DOI：10.1007/s10593-014-1424-4

  日期：2014.3

  The synthesis and antimicrobial evaluation of a series of chromone-linked substituted heterocyclic derivatives is described. The condensation of 3-formylchromone with acetoacetamide under Knoevenagel–Cope reaction conditions was also explored, and the condensation with 4-hydroxy-6-methyl-2H-pyran-2-one constitutes a facile route to pyranopyrone fused systems. Most of the compounds exhibit good antimicrobial

  描述了一系列色酮连接的取代杂环衍生物的合成和抗菌评估。还研究了在Knoevenagel–Cope反应条件下3-甲酰基色酮与乙酰乙酰胺的缩合，并且与4-羟基-6-甲基-2 H-吡喃-2-酮的缩合构成了吡喃并吡喃稠合体系的便捷途径。大多数化合物显示出良好的抗菌性能。