1-indanone thiosemicarbazone | 74227-66-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 1-indanone thiosemicarbazone
• 英文别名: FM00310；1-indanone TSC；(2,3-dihydroinden-1-ylideneamino)thiourea
• CAS: 74227-66-0
• 化学式: C₁₀H₁₁N₃S
• mdl: MFCD21101633
• 分子量: 205.283
• InChiKey: WFHFUKVEUQNVSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-indanone thiosemicarbazone 、 alpha-氯乙酰苯 以 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到2-(2-(2,3-dihydro-1H-inden-1-ylidene)hydrazinyl)-4-phenylthiazole
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 1-indanone thiazolylhydrazone derivatives as anti-Trypanosoma cruzi agents

  摘要：

  A series of novel 4-arylthiazolylhydrazones (TZHs) derived from 1-indanones were synthesized in good yields (66-92%) in a simple procedure using microwave irradiation and then characterized by spectroscopy studies. The compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against the epimastigote, trypomastigote and amastigote forms of the parasite. Most TZHs displayed excellent activity, and were more potent and selective than the reference drug Benznidazole, used in the current chemotherapy. Analysis of the free sterols from parasite incubated with the compounds showed that inhibition of ergosterol biosynthesis is a possible target for the action of these new TZHs. In particular, TZH 9 emerged as a promising antichagasic compound to be evaluated in animal models. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.013
• 作为产物：
  描述：

  氨基硫脲 、 1-茚酮 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 1-indanone thiosemicarbazone
  参考文献：
  名称：

  氨基硫脲与 DMAD 的高效“水上”绿色路线杂环化

  摘要：

  图形摘要 摘要 报道了一种简单、高效且环保的方法，用于在水中通过缩氨基硫脲衍生物和二甲基乙炔二羧酸酯 (DMAD) 的环缩反应以良好的收率合成 thiazolidin-4-one 衍生物。环化产物的区域化学是通过元素分析、IR、NMR 和质谱数据确定的。报告了代表性化合物 3f 的单晶 X 射线衍射研究。

  DOI：

  10.1080/10426507.2015.1073282

文献信息

• Synthesis and evaluation of biological activities of 4-cyclopropyl-5-(2-fluorophenyl) arylhydrazono-2,3-dihydrothiazoles as potent antioxidant agents
  作者：F. Ghanbari Pirbasti、Nosrat O. Mahmoodi、Jafar Abbasi Shiran

  DOI：10.1080/17415993.2015.1122009

  日期：2016.3.3

  high purities. Antioxidant activity of products was evaluated using DPPH (2,2-diphenyl-2-picrylhydrazyl) and ABTS 2,2-azinobis(3-ethylbenzothiazoline-sulfonate) assays. Products showed higher antioxidant activity using the ABTS method. Compounds 5c and 5g showed lower IC50 values compared with ascorbic acid as a standard. Compounds 5a–5h possessed moderate to high antioxidant activity by both methods

  通过制备的缩氨基硫脲与 2-溴-1-环丙基-2-(2-氟苯基)乙酮反应合成了一系列新的 4-环丙基-5-(2-氟苯基)芳基肼基-2,3-二氢噻唑衍生物。通过半 Hantzsch 环化，Et3N 作为催化剂的存在。实现了该一锅反应的优化反应条件。反应时间短、收率高、纯度高。使用 DPPH（2,2-二苯基-2-picrylhydrazyl）和 ABTS 2,2-azinobis(3-ethylbenzothiazoline-sulfonate) 测定法评估产品的抗氧化活性。使用 ABTS 方法，产品显示出更高的抗氧化活性。与作为标准的抗坏血酸相比，化合物 5c 和 5g 显示出较低的 IC50 值。通过两种方法，化合物 5a-5h 都具有中到高的抗氧化活性。还，针对革兰氏阳性和革兰氏阴性细菌菌株评估了 5a-5h 的抗菌活性。这些化合物均不抑制嗜水曲霉，而它们对其他测试的细菌菌株具有中到低的抑制活性。图形概要
• Synthesis, Structural Characterization, and Pro-apoptotic Activity of 1-Indanone Thiosemicarbazone Platinum(II) and Palladium(II) Complexes: Potential as Antileukemic Agents
  作者：Natalia Gómez、Diego Santos、Ramiro Vázquez、Leopoldo Suescun、Álvaro Mombrú、Monica Vermeulen、Liliana Finkielsztein、Carina Shayo、Albertina Moglioni、Dinorah Gambino、Carlos Davio

  DOI：10.1002/cmdc.201100060

  日期：2011.8.1

  against leukemia, various 1‐indanone thiosemicarbazones, as well as eight novel platinum(II) and palladium(II) complexes, with the formula [MCl2(HL)] and [M(HL)(L)]Cl, derived from two 1‐indanone thiosemicarbazones were synthesized and tested for antiproliferative activity against the human leukemia U937 cell line. The crystal structure of [Pt(HL1)(L1)]Cl.2MeOH, where L1=1‐indanone thiosemicarbazone

  在寻找针对白血病的替代化学治疗策略时，各种1-茚满酮硫代半碳唑酮以及八种新颖的具有[MCl 2（HL）]和[M（HL）（L ）的铂（II）和钯（II）配合物）]合成源自两个1-茚满酮硫代半咔唑酮的Cl并测试其对人白血病U937细胞系的抗增殖活性。[Pt（HL1）（L1）] Cl的晶体结构。2 M通过X射线衍射解决了eOH，其中L1 = 1-茚满酮硫代半碳酮。游离的硫半脲配体未显示出抗增殖作用，但相应的铂（II）和钯（II）配合物抑制细胞增殖并诱导凋亡。铂（II）配合物在U937细胞中也显示选择性凋亡活性，但在外周血单核细胞或用于筛选潜在肝毒性的人肝细胞癌HepG2细胞系中则没有。目前的发现表明，在U937细胞中，与钯（II）配位的化合物相比，与钯（II）配位的1-茚满酮硫代半碳氮酮的细胞毒性更高，尽管发现后者对白血病细胞更具选择性，表明它们是具有前景的化合物。针对血液恶性肿瘤的潜在治疗应用。
• Nazim, Urooj; Narayanan, Silpa; Ali, Mohsin, Journal of the Chemical Society of Pakistan, 2021, vol. 43, # 2, p. 244 - 252
  作者：Nazim, Urooj、Narayanan, Silpa、Ali, Mohsin、Khan, Khalid Mohammed、Ali, Basharat、Li, Jonathan、Chen, Zhe-Sheng、Ahmed, Mansoor、Yang, Dong-Hua

  DOI：——

  日期：——
• Thiosemicarbazones derived from 1-indanones as new anti-Trypanosoma cruzi agents
  作者：María E. Caputto、Lucas E. Fabian、Diego Benítez、Alicia Merlino、Natalia Ríos、Hugo Cerecetto、Graciela Y. Moltrasio、Albertina G. Moglioni、Mercedes González、Liliana M. Finkielsztein

  DOI：10.1016/j.bmc.2011.09.037

  日期：2011.11

  In the present work, we synthesized a series of thiosemicarbazones derived from 1-indanones with good anti-Trypanosoma cruzi activity. Most of them displayed remarkable trypanosomicidal activity. All the compounds showed nonspecific cytotoxicity on human erythrocytes. The ability of the new compounds to inhibit cruzipain, the major cysteine protease of T. cruzi, was also explored. Thiosemicarbazones 12 and 24 inhibited this enzyme at the dose assayed. This interaction was also studied in terms of molecular docking. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of some novel 1-indanone thiazolylhydrazone derivatives as anti-Trypanosoma cruzi agents
  作者：María E. Caputto、Alejandra Ciccarelli、Fernanda Frank、Albertina G. Moglioni、Graciela Y. Moltrasio、Daniel Vega、Elisa Lombardo、Liliana M. Finkielsztein

  DOI：10.1016/j.ejmech.2012.07.013

  日期：2012.9

  A series of novel 4-arylthiazolylhydrazones (TZHs) derived from 1-indanones were synthesized in good yields (66-92%) in a simple procedure using microwave irradiation and then characterized by spectroscopy studies. The compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against the epimastigote, trypomastigote and amastigote forms of the parasite. Most TZHs displayed excellent activity, and were more potent and selective than the reference drug Benznidazole, used in the current chemotherapy. Analysis of the free sterols from parasite incubated with the compounds showed that inhibition of ergosterol biosynthesis is a possible target for the action of these new TZHs. In particular, TZH 9 emerged as a promising antichagasic compound to be evaluated in animal models. (C) 2012 Elsevier Masson SAS. All rights reserved.