indole-2,3-dione 3-thiosemicarbazone | 1165809-20-0

• 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: indole-2,3-dione 3-thiosemicarbazone
• 英文别名: 2-(1,2-dihydro-2-oxo-3H-indol-3-ylidenyl)thiosemicarbazone；1-(2-oxoindolin-3-ylidene)thiosemicarbazide；3-(indolin-2-one)hydrazinecarbothioamide；1H-indole-2,3-dione-3-thiosemicarbazone；isatin β-thiosemicarbazone；isatin-β-thiosemicarbazide
• CAS: 1165809-20-0
• 化学式: C₉H₈N₄OS
• mdl: MFCD00043581
• 分子量: 220.255
• InChiKey: SLEMRAMJSGBARH-UHFFFAOYSA-N

物化性质

• 沸点：
  437.9±55.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.51
• 氢给体数：
  3.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  indole-2,3-dione 3-thiosemicarbazone 生成 ethyl ester of (1,2,4-triazino[5,6-b]indolyl-3-thio)acetic acid
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 生成 indole-2,3-dione 3-thiosemicarbazone
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Back to the Coordination Modes of the Thiosemicarbazonate Chain: New Insights from Diorganolead(IV) and Lead(II) Derivatives of Isatin‐3‐thiosemicarbazone
  作者：José S. Casas、Noelia Casanova、María S. García‐Tasende、Agustín Sánchez、José Sordo、Ángeles Touceda、Saulo Vázquez

  DOI：10.1002/ejic.201000669

  日期：2010.11

  kinetically controlled O,N 2 ,S isomer formed first due to the rigidity of the ligand. If the compound remains in solution, slow partial evolution to the O,N 3 ,S isomer occurs. DFT calculations predict that [Pb(OAc)(N 3 -L 1 )] is slightly more stable than [Pb(OAc)(N 2 -L 1 )] both in the gas phase and in DMSO solution. The calculations also modelled structures for the two isomers close to those obtained

  在赤道平面上具有顶端苯基和 O,N x ,S-配位的 L x- 和异双齿 AcO - 配体。在 [PbPh 2 (OAc)(N 2 -L 1 )]·MeOH·EtOH 中，(N 2 -L 1 ) - 配体与金属形成四元和六元螯合环，而在 PbPh 2 ( OAc)(N 3 -L 2 )]·H 2 O 由(N 3 -L 2 ) - 形成的两个螯合环是五元的。从同一溶液中分离出的 Pb II 复合物 [Pb(OAc)(N 2 -L 1 )] 和 [Pb(OAc)(N 3 -L 1 )] 是连接异构体。这些化合物具有相当不规则的立体化学，表明存在立体化学活性的孤电子对；在 [Pb(OAc)(N 2 -L 1 )] 中，(L 1 ) - 配体是 O,N 2 ,S-配位，在 [Pb(OAc)(N 3 -L 1 )] 中，该配体是 O， N 3 ,S-配位。通过 1 H 和 13 C NMR 光谱分析
• Structural improvement of new thiazolyl-isatin derivatives produces potent and selective trypanocidal and leishmanicidal compounds
  作者：Luiz Alberto Barros Freitas、Aline Caroline da Silva Santos、Gedália de Cássia Silva、Franciely Nayara do Nascimento Albuquerque、Elis Dionísio Silva、Carlos Alberto de Simone、Valéria Rêgo Alves Pereira、Luiz Carlos Alves、Fabio André Brayner、Ana Cristina Lima Leite、Paulo André Teixeira de Moraes Gomes

  DOI：10.1016/j.cbi.2021.109561

  日期：2021.8

  Thus, compounds 2l and 2m showed dual in vitro trypanosomicidal and leishmanicidal activities. A structural activity relationship study showed that thiazolyl-isatin derivatives from phenyl-thiosemicarbazone (2a-m) were, in general, more active than thiazolyl-isatin derivatives from thiosemicarbazone (1a-g). Crystallography studies revealed a different configuration between series 1a-g and 2a-m. The configuration

  被忽视的疾病是一组主要发生在热带气候国家的传染性疾病。在这一群体中，恰加斯病和利什曼病最为突出，被认为是对全球健康的威胁。这些疾病的治疗是有限的。因此，需要针对这些疾病的新疗法。从这个意义上说，我们的提议包括开发两个系列的化合物，使用杂环靛红和噻唑的分子杂交。靛红和噻唑环是多种生物疾病（包括抗寄生虫疾病）的重要支架。在本文中，噻唑基-靛红是由各自的缩氨基硫脲或苯基-缩氨基硫脲合成的，这些新的噻唑基-靛红对锥鞭毛体有毒，而不影响巨噬细胞的活力。从这个系列，化合物2e(IC 50 = 4.43 μM)、2j (IC 50 = 2.05 μM)、2l (IC 50 = 4.12 μM) 和2m (1.72 μM) 对锥鞭毛体形式表现出最佳的抗克氏锥虫活性，其选择性指数高于苯并硝唑(BZN)。化合物2j、2l和2m能够诱导与锥体鞭毛体坏死相容的显着标记。扫描电子显微镜分析表明，用来自IC 50的化合物2m处理的T
• 1H,13C,15N and19F NMR study of acetylation products of heterocyclic thiosemicarbazones
  作者：Lyudmila I. Larina、Valentina N. Elokhina、Tatyana I. Yaroshenko、Anatolii S. Nakhmanovich、Gennadii V. Dolgushin

  DOI：10.1002/mrc.2006

  日期：2007.8

  eryl)‐1,3,4‐thiadiazoles, and some of their salts were prepared and studied by multinuclear 1H, 13C, 15N, 19F and 2D NMR spectroscopy. The acetylation of thiosemicarbazones is accompanied by ring closure to form the corresponding 1,3,4‐thiadiazolines and 1,3,4‐thiadiazoles. 15N NMR spectroscopy is a unique method for the identification of thiadiazole pyridinium salts. Copyright © 2007 John Wiley &

  制备了新型 2-乙酰氨基-4-乙酰基-5-芳基(杂基)-1,3,4-噻二唑啉、2-乙酰氨基-5-芳基(杂基)-1,3,4-噻二唑及其部分盐并通过多核 1H、13C、15N、19F 和 2D 核磁共振波谱研究。缩氨基硫脲的乙酰化伴随着闭环形成相应的 1,3,4-噻二唑啉和 1,3,4-噻二唑。15N NMR 光谱是鉴定噻二唑吡啶鎓盐的独特方法。版权所有 © 2007 John Wiley & Sons, Ltd.
• Assessment of 5-substituted Isatin as Surface Recognition Group: Design, Synthesis, and Antiproliferative Evaluation of Hydroxamates as Novel Histone Deacetylase Inhibitors
  作者：Avineesh Singh、Kamlesh Raghuwanshi、Vijay K Patel、Deepak K Jain、Ravichandran Veerasamy、Anshuman Dixit、Harish Rajak

  DOI：10.1007/s11094-017-1616-1

  日期：2017.8

  Histone deacetylase (HDAC) is a promising target for cancer treatment. HDAC inhibitors consist of three pharmacophoric features: an aromatic cap group, zinc binding group (ZBG), and a linker chain connecting cap group to ZBG. Herein, we report on (i) substituted isatin moiety as the cap group that recognizes the surface of active enzyme pocket and (ii) thiosemicarbazide moiety incorporated as linker group responsible for connecting the cap group to ZBG (hydroxamic acid). The synthesized compounds were evaluated for their antiproliferative activity and HDAC enzyme inhibition. The binding mode analysis of proposed compounds was evaluated by docking studies. Several analogs were found to inhibit HDAC and cellular proliferation of Hela cervical cancer cells, with GI50 values in the micromolar range. One compound (Vd) was found to have greater in vitro antiproliferative activity in comparison to other compounds.

  组蛋白去乙酰化酶（HDAC）是癌症治疗的潜在靶点。HDAC抑制剂由三种药效团特征组成：芳香的帽状基团、锌结合基团（ZBG）以及连接帽状基团与ZBG的链接链。本文报道了（i）取代的异吲哚酮部分作为帽状基团，识别活性酶口袋表面，以及（ii）结合为链接基团负责连接帽状基团与ZBG（羟肟酸）的酰肼部分。所合成的化合物进行了抗增殖活性和HDAC酶抑制活性的评估。通过对接研究评估了所提出化合物的结合模式。发现多个类似物能够抑制HDAC及宫颈癌Hela细胞的增殖，其GI50值在微摩尔范围内。其中一个化合物（Vd）相较于其他化合物显示出更强的体外抗增殖活性。
• Identification and preliminary structure–activity relationships of 1-Indanone derivatives as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors
  作者：Dingding Gao、Yingxia Li

  DOI：10.1016/j.bmc.2017.05.017

  日期：2017.7

  Indoleamine 2,3-dioxygenase 1 (IDO1) plays a vital role in the catabolism of tryptophan along with the kynurenine pathway which is involved in many human diseases including cancer, Alzheimer’s disease, etc. In this study, compound 1 bearing a 1-Indanone scaffold was identified as a novel IDO1 inhibitor by structure-based virtual screening, with moderate to good enzymatic and cellular inhibitory activities

  吲哚胺2,3-双加氧酶1（IDO1）与色氨酸途径一起在色氨酸的分解代谢中起着至关重要的作用，该过程涉及许多人类疾病，包括癌症，阿尔茨海默氏病等。在这项研究中，化合物1带有1-茚满酮支架通过基于结构的虚拟筛选被鉴定为新型IDO1抑制剂，具有中等至良好的酶促和细胞抑制活性。此外，表面等离子体共振分析验证了化合物1和IDO1蛋白之间的直接相互作用。进一步探索了初步SAR，并通过实验和分子对接预测了与IDO1蛋白的结合方式。随后对这些活性化合物的ADME特性进行了计算机分析，结果显示出良好的药代动力学效率。我们认为，这项研究为高效IDO1抑制剂的未来发展做出了巨大贡献，促进了结构多样性。