1-methylindole-3-carboxaldehyde thio semicarbazone | 103907-05-7

• 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: 1-methylindole-3-carboxaldehyde thio semicarbazone
• 英文别名: 2-((1-methyl-1H-indol-3-yl)methylene)hydrazinecarbothioamide；[(1-methylindol-3-yl)methylideneamino]thiourea
• CAS: 103907-05-7
• 化学式: C₁₁H₁₂N₄S
• 分子量: 232.309
• InChiKey: GBYGDAYEMDUQKP-UHFFFAOYSA-N

物化性质

• 熔点：
  200.3-201.2 °C
• 沸点：
  436.0±37.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  87.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 在 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 10.0h， 生成 1-methylindole-3-carboxaldehyde thio semicarbazone
  参考文献：
  名称：

  芳硫半脲用作抗霉菌剂

  摘要：

  在筛选过程的基础上，我们将取代的硫半脲靶向为潜在的抗菌药。我们的目标是确定有助于抗寄生虫活性的关键结构要素，这些要素可用于开发有效的药物。合成了一系列的32种化合物，并评估了其对利什曼原虫的临床相关细胞内酰胺的功效。从这些化合物中，有22种化合物的EC 50值低于10μM，活性最高的衍生物（化合物14）的EC 50值为50在两个不同的哺乳动物细胞系中，其毒性仅为0.8μM，毒性极低。更高活性所需的最相关的结构元素表明，存在稠合的双环芳环如带有烷基或烷氧基取代基的萘是先决条件。由于易于合成，高活性和低毒性，最具活性的化合物可被视为进一步开发的先导。

  DOI：

  10.1016/j.ejmech.2016.07.014

文献信息

• Photochromic behavior and mechanism of indole thiosemicarbazide derivates in amorphous powder, solution and nanofiber
  作者：Yuanyuan Che、Lang Liu、Jianzhang Zhao、Yuming Yu、Xianmei Zhao

  DOI：10.1016/j.dyepig.2019.04.009

  日期：2019.10

  reversible photochromic properties both in solid−solid state and solution. Moreover, the nanofiber containing the compound 4 also shows excellent photochromic properties, which are better than the amorphous powder of 4 itself. Based on the experiment results and theoretical calculation, we confirm that the photochromic properties originate from the intermolecular proton transfer, resulting in the isomerization

  合成了一系列含有吲哚基团的席夫碱。化合物2-[（（1-甲基-1H-吲哚-3-基）亚甲基]肼基甲硫基酰胺（4）在固-固状态和溶液状态下均表现出优异的可逆光致变色特性。此外，含有化合物4的纳米纤维还显示出优异的光致变色性能，优于4的无定形粉末。本身。根据实验结果和理论计算，我们确认光致变色性质源自分子间质子转移，从而导致肼基碳硫代酰胺中的硫酮型和硫醇型异构化。这种独特的光致变色系统显然不同于传统的席夫碱，例如水杨基苯胺。
• Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones
  作者：Vida Mashayekhi、Kamaleddin Haj Mohammad Ebrahim Tehrani、Parisa Azerang、Soroush Sardari、Farzad Kobarfard

  DOI：10.1007/s12272-013-0242-z

  日期：2021.8

  Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two-step methodology including N-alkylation(benzylation) of indole-3-carboxaldehyde and conversion of the intermediate aldehydes to corresponding thiosemicarbazones. The derivatives were evaluated for their antimycobacterial activity and compounds 3d (R = propyl) and 3q (R = 4-nitrobenzyl) were among the most potent and selective derivatives with IC50 values of 0.9 and 1.9 μg/mL respectively. The anticancer activity of the derivatives was also assessed against a panel of tumor cell lines. Compounds 3t, 3u, 3v and 3w efficiently inhibited the majority of the cancer cell lines with considerable selectivity.

  基于生物活性吲哚类化合物的结构元素，合成了一系列新型1-取代吲哚-3-甲酰基缩氨基硫脲作为潜在的抗分枝杆菌和抗癌剂。这些衍生物通过两步法合成：包括吲哚-3-甲酰基的N-烷基化（苄基化）以及中间体醛转化为相应的缩氨基硫脲。评估了这些衍生物的抗分枝杆菌活性，其中化合物3d（R = 丙基）和3q（R = 4-硝基苄基）是活性最强且选择性最高的衍生物，其IC50值分别为0.9和1.9 μg/mL。还评估了这些衍生物对一组肿瘤细胞系的抗癌活性。化合物3t、3u、3v和3w能有效抑制大多数癌细胞系，并具有相当的选择性。
• Synthesis and Structure−Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain
  作者：Xiaohui Du、Chun Guo、Elizabeth Hansell、Patricia S. Doyle、Conor R. Caffrey、Tod P. Holler、James H. McKerrow、Fred E. Cohen

  DOI：10.1021/jm010459j

  日期：2002.6.1

  American trypanosomiasis, or Chagas' disease, is the leading cause of heart disease in Latin America. Currently there is an urgent need to develop antitrypanosomal therapy due to the toxicity of existing agents and emerging drug resistance. A novel series of potent thio semicarbazone small-molecule inhibitors of the Trypanosoma cruzi cysteine protease cruzain have been identified. Some of these inhibitors have been shown to be trypanocidal. We initially discovered that X-bromopropiophenone thio semicarbazone (1i) inhibited cruzain and could cure mammalian cell cultures infected with T cruzi. 3'-Bromopropiophenone thio semicarbazone showed no toxicity for mammalian cells at concentrations that were trypanocidal. Following this lead, more than 100 compounds were designed and synthesized. A specific structure-activity relationship (SAR) was established, and many potent analogues with IC50 values in the low nanomolar range were identified. Eight additional analogues were trypanocidal in a cell culture assay, and this indicates that aryl thio semicarbazone is a productive scaffold for killing the parasites. Kinetic studies show that these are time-dependent inhibitors. Molecular modeling studies of the enzyme-inhibitor complex have led to a proposed mechanism of interaction as well as insight into the SAR of the thio semicarbazone series. The nonpeptide nature of this series, small size, and extremely low cost of production suggest this is a promising direction for the development of new antitrypanosome chemotherapy.
• Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase
  作者：Wei Yi、Carole Dubois、Samir Yahiaoui、Romain Haudecoeur、Catherine Belle、Huacan Song、Renaud Hardré、Marius Réglier、Ahcène Boumendjel

  DOI：10.1016/j.ejmech.2011.07.003

  日期：2011.9

  Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into L-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Arylthiosemicarbazones as antileishmanial agents
  作者：José Ignacio Manzano、Florent Cochet、Benjamin Boucherle、Verónica Gómez-Pérez、Ahcène Boumendjel、Francisco Gamarro、Marine Peuchmaur

  DOI：10.1016/j.ejmech.2016.07.014

  日期：2016.11

  the most active derivative (compound 14) showing an EC50 of 0.8 μM with very low toxicity on two different mammalian cell lines. The most relevant structural elements required for higher activity indicate that the presence of a fused bicyclic aromatic ring such as a naphthalene bearing an alkyl or an alkoxy group substituent are prerequisites. Owing to the easy synthesis, high activity and low toxicity

  在筛选过程的基础上，我们将取代的硫半脲靶向为潜在的抗菌药。我们的目标是确定有助于抗寄生虫活性的关键结构要素，这些要素可用于开发有效的药物。合成了一系列的32种化合物，并评估了其对利什曼原虫的临床相关细胞内酰胺的功效。从这些化合物中，有22种化合物的EC 50值低于10μM，活性最高的衍生物（化合物14）的EC 50值为50在两个不同的哺乳动物细胞系中，其毒性仅为0.8μM，毒性极低。更高活性所需的最相关的结构元素表明，存在稠合的双环芳环如带有烷基或烷氧基取代基的萘是先决条件。由于易于合成，高活性和低毒性，最具活性的化合物可被视为进一步开发的先导。