1H-3-(2'-oxa-3',4'-diazolyl)indole | 82380-80-1

• 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: 1H-3-(2'-oxa-3',4'-diazolyl)indole
• 英文别名: 2-(1H-indol-3-yl)-1,3,4-oxadiazole；3-(1,3,4-oxadiazol-2-yl)-1H-indole；2-(3-indolyl)-1,3,4-oxadiazole；Indole, 3-(1,3,4-oxadiazol-2-yl)-
• CAS: 82380-80-1
• 化学式: C₁₀H₇N₃O
• mdl: MFCD00466606
• 分子量: 185.185
• InChiKey: RNQOXZZZQQAXPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C(Solv: ethanol (64-17-5))
• 沸点：
  412.2±47.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

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：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-3-(2'-oxa-3',4'-diazolyl)indole 、 氯乙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到methyl [3-(1,3,4-oxadiazol-2-yl)-1H-indol-1-yl]acetate
  参考文献：
  名称：

  Synthesis and functionalization of the 3-(1,3,4-oxadiazol-2-yl)-1h-indoles

  摘要：

  A modified method is proposed for the preparative synthesis of 3-(1,3,4-oxadiazol-2-yl)-1H-indoles in high yield. We are the first to demonstrate the functionalization of this heterocyclic system by alkylation. In particular, syntheses are reported for [3-(1,3,4-oxadiazol-2-yl)-1H-indol-1-yl]acetic acids and their amide derivatives.

  DOI：

  10.1007/s10593-010-0418-0
• 作为产物：
  描述：

  1-(3-carboxyindolyl)-2-formylhydrazide 在 三氯氧磷 作用下， 反应 12.0h， 以72%的产率得到1H-3-(2'-oxa-3',4'-diazolyl)indole
  参考文献：
  名称：

  基于植物抗毒素Camalexin支架的真菌解毒酶Brassinin氧化酶的合成抑制剂。

  摘要：

  Brassinin（1）是十字花科（俗称十字花科）的植物中必需的植物抗毒素，因为它是其他植物抗毒素的生物合成前体，并具有抗菌活性。Brassinin（1）的二硫代氨基甲酸酯类是其相当广泛的抗真菌活性的毒素。对许多农业上重要的农作物有害，十字花科的几种致病真菌能够通过解毒克服油菜素。在这项工作中，使用植物病原性真菌Leptosphaeria maculans（无性阶段Phoma lingam）产生的植物抗毒素解毒酶brasinin氧化酶抑制剂），进行了合成和评估。camalexin支架用于设计braxinin氧化酶抑制剂（即paldoxins，phytoalexin解毒抑制剂），因为camalexin是不是由芸苔属产生的phyalealexin，而L. maculans无法代谢。卡马新及其衍生物的抑制作用降低如下：5-甲氧基卡马新> 5-氟卡马新= 6-甲氧基卡马新>卡马新> 6-氟卡马新;

  DOI：

  10.1021/jf803666s

文献信息

• ACYL-HYDRAZONE AND OXADIAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND USES THEREOF
  申请人：Universidade Federal de Santa Catarina

  公开号：US20150191445A1

  公开（公告）日：2015-07-09

  The present invention relates to acyl-hydrazone compounds, in particular 3,4,5-trimethoxyphenyl-hydrazide derivatives, as well as the oxadiazole analogs thereof and other similar compounds, and to the pharmaceutical use of the same for the treatment of various diseases associated with cell proliferation, such as leukemias, including acute lymphoblastic leukemia (ALL), tumours and inflammation. Acyl-hydrazones have been obtained having activity similar to that of the compound used as a standard in experiments (colchicine). The greater selectivity of the compounds according to the invention is an important feature, associated with fewer side effects than the pharmaceuticals used at present in clinical treatments. The synthetised acyl-hydrazones, more particularly the compounds 02 and 07, exhibited important antileukemic activity, which suggests 02 and 07 as candidates to pharmaceutical prototypes, or to pharmaceuticals for the treatment of leukemias, in particular acute lymphoblastic leukemia (ALL), tumours and other proliferative diseases, such as inflammation. The action mechanism of the most active compounds was determined by using DNA microarrays and subsequent tests indicated by the chip, besides selectivity studies in healthy human lymphocytes.

  本发明涉及酰基腙化合物，特别是3,4,5-三甲氧基苯基腙衍生物，以及其噁二唑类似物和其他类似化合物，以及它们在治疗与细胞增殖相关的各种疾病，如白血病（包括急性淋巴细胞白血病（ALL））、肿瘤和炎症方面的药用。已获得具有与实验中使用的化合物（秋水仙碱）相似活性的酰基腙。根据本发明的化合物具有更大的选择性，与目前在临床治疗中使用的药物相比，副作用更少是一个重要特征。合成的酰基腙，尤其是化合物02和07，表现出重要的抗白血病活性，这表明02和07可能成为药物原型的候选，或用于治疗白血病，特别是急性淋巴细胞白血病（ALL）、肿瘤和其他增殖性疾病，如炎症的药物。最活性化合物的作用机制是通过使用DNA微阵列确定的，并且通过芯片指示的后续测试，以及对健康人类淋巴细胞的选择性研究。
• [4 + 1] Cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5
  作者：Ya Wang、Shiqiang Mu、Xin Li、Qiuling Song

  DOI：10.1016/j.cclet.2021.08.089

  日期：2022.3

  A facile synthesis of 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5 via [4 + 1] cyclization of ClCF2COONa with non-amine compounds containing amino groups is developed. Of note, this is the first time that halofluorinated compounds are used as C1 synthon to construct deuterated nitrogen-heterocyclic compounds. The current protocol features simple operation, readily accessible raw materials, wide substrate

  1,3,4-恶二唑和1,3,4-恶二唑-d 5 通过ClCF 2 COONa 与含有氨基的非胺化合物的[4 + 1] 环化而简便地合成。值得注意的是，这是首次将卤代氟化合物作为C1合成子构建氘代氮杂环化合物。目前的协议具有操作简单、原料易得、底物范围广和产品价值高等特点
• Synthesis and properties of azoles and their derivatives. 33. Synthesis of 1,3,4-oxadiazoles that contain an indolyl group
  作者：V. I. Kelarev、G. A. Shvekhgeimer

  DOI：10.1007/bf00522123

  日期：1982.3
• MONGE, VEGA, A.;RABBANI, M. M.;FERNANDEZ-ALVAREZ, E., BOL. SOC. QUIM. PERU., 1983, 49, N 2, 120-130
  作者：MONGE, VEGA, A.、RABBANI, M. M.、FERNANDEZ-ALVAREZ, E.

  DOI：——

  日期：——
• [EN] ACYL-HYDRAZONE AND OXADIAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND USES THEREOF<br/>[FR] COMPOSÉS ACYL-HYDRAZONES ET OXADIAZOLS, COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT ET UTILISATIONS CORRESPONDANTES<br/>[PT] "COMPOSTOS ACIL-HIDRAZONAS E OXADIAZÓIS, COMPOSIÇÕES FARMACÊUTICAS COMPREENDENDO OS MESMOS E SEUS USOS
  申请人：UNIV FED DE SANTA CATARINA UFSC

  公开号：WO2013075199A1

  公开（公告）日：2013-05-30

  A presente invenção refere-se a compostos acil-hidrazonas, especialmente as derivados da 3,4,5-trimetoxifenil-hidrazida, bem como a seus análogos oxadiazóis e outros compostos semelhantes, e aplicação farmacêutica dos mesmos no tratamento de diferentes doenças associadas à proliferação celular, como leucemias, incluindo leucemia linfóide aguda (LLA), tumores e inflamação. Foram obtidas acil-hidrazonas com atividade semelhante ao composto utilizado como padrão nos experimentos (colchicina). A maior seletividade dos compostos apresentados nesta invenção é uma característica importante relacionada com menores efeitos colaterais que os fármacos atualmente empregados na clínica. As acil- hidrazonas sintetizadas, mais especificamente os compostos 02 e 07, apresentaram importante atividade antileucêmica, o que indica 02 e 07 como candidatos a protótipos de fármacos, ou fármacos, para o tratamento de leucemias, especialmente leucemia linfóide aguda (LLA), tumores e outras doenças proliferativas, como inflamação. A determinação do mecanismo de ação dos compostos mais ativos foi realizada pela utilização de microarranjos de DNA e testes subsequentes indicados através do chip, além dos estudos de seletividade em linfócitos humanos saudáveis.