2-[(3-甲酰基-1H-吲哚-1-基)甲基]-苯甲腈 | 340319-15-5

• 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
• 中文名称: 2-[(3-甲酰基-1H-吲哚-1-基)甲基]-苯甲腈
• 英文名称: 1‑(2‑cyanobenzyl)‑1H‑indole‑3‑carboxaldehyde
• 英文别名: 1-(2-cyanobenzyl)indole-3-carboxaldehyde；2-[(3-formyl-1H-indol-1-yl)methyl]benzonitrile；2-[(3-formylindol-1-yl)methyl]benzonitrile
• CAS: 340319-15-5
• 化学式: C₁₇H₁₂N₂O
• mdl: MFCD02197488
• 分子量: 260.295
• InChiKey: NOWKHVRSYCMZFU-UHFFFAOYSA-N

物化性质

• 沸点：
  496.9±30.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-[(3-甲酰基-1H-吲哚-1-基)甲基]-苯甲腈 在 哌啶 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.0h， 生成 (E)-N-(5-(benzylsulfanyl)-1,3,4-thiadiazol-2-yl)-2-cyano-3-(1-((2-cyanophenyl)methyl)-1H-indol-3-yl)prop-2-enamide
  参考文献：
  名称：

  Identification of novel thiadiazoloacrylamide analogues as inhibitors of dengue-2 virus NS2B/NS3 protease

  摘要：

  Dengue virus is endemic throughout tropical and subtropical regions, and cause severe epidemic diseases. The NS2B/NS3 protease is a promising drug target for dengue virus. Herein, we report the discovery and modification of a novel class of thiadiazoloacrylamide derivatives with potent inhibitory activity against the NS2B/NS3 protease. Thiadiazolopyrimidinone 1 was firstly determined as a new chemical structure against NS2B/NS3 from a commercial compound library. Then, we sought to identify similar compounds with the thiadiazoloacrylamide core that would exhibit better activity. A series of analogues were synthesized and fourteen of them were identified with strong inhibitory activities, in which the nitrile group in the linker part was discovered as an essential group for the inhibitory activity. The best of these (8b) demonstrated an IC50 at 2.24 mu M based on in vitro DENV2 NS2B-NS3pro assays. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.09.057
• 作为产物：
  描述：

  3-吲哚甲醛 、 邻氰基氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-[(3-甲酰基-1H-吲哚-1-基)甲基]-苯甲腈
  参考文献：
  名称：

  吲哚系列新型缩氨基硫脲和噻唑烷酮类化合物的合成及抗菌活性

  摘要：

  摘要 在吲哚衍生物与缩氨基硫脲的极好产率反应中合成了新的缩氨基硫脲。这些缩氨基硫脲与溴乙酸乙酯反应生成具有4-氧代-噻唑烷基团的原始杂环取代吲哚衍生物。进行分析IR和NMR光谱以及元素分析以揭示它们的结构。对所有合成化合物的抗菌活性进行了体外抗革兰氏阳性菌和革兰氏阴性菌的抗菌活性评估。抗菌筛选数据显示两种化合物对金黄色葡萄球菌、大肠杆菌和铜绿假单胞菌具有活性。. 这些初步结果表明，这些新合成的化合物中的一些显示出有希望的抗菌效力。 图形摘要

  DOI：

  10.1007/s00706-021-02823-6

文献信息

• 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。
• Novel<i>N</i>-Substituted ((1<i>H</i>-indol-3-yl)methylene)benzohydrazides and ((1<i>H</i>-indol-3-yl)methylene)-2-phenylhydrazines: Synthesis and Antiplatelet Aggregation Activity
  作者：Nadia Kalhor、Matin Mardani、Sepideh Abdollahzadeh、Mona Vakof、Marjan Esfahani Zadeh、Kamaleddin Haj Mohammad Ebrahim Tehrani、Farzad Kobarfard、Shohreh Mohebbi

  DOI：10.1002/bkcs.10531

  日期：2015.11

  antiplatelet hydrazone derivatives, some new indole‐based derivatives were designed and synthesized as potential antiplatelet agents. Synthesis of the derivatives was accomplished by substitution at the N – 1 position of indole‐3‐carboxaldehyde and reacting the resulting intermediates with either phenylhydrazine of benzoylhydrazide. The structure of the synthesized compounds was confirmed by different spectral

  根据我们先前对抗血小板衍生物的研究，设计并合成了一些新的基于吲哚的衍生物作为潜在的抗血小板药。衍生物的合成是通过在 吲哚-3-羧醛的N -1位进行取代并使所得的中间体与苯甲酰肼的苯肼反应而完成的。合成的化合物的结构通过质谱，1 H-NMR和IR光谱等不同的光谱方法得到证实。测试了这些衍生物抑制人血小板聚集的能力，其中花生四烯酸（AA），二磷酸腺苷ADP和胶原蛋白被用作聚集诱导剂。化合物（2a–2f）对AA诱导的血小板聚集表现出相当大的活​​性。其中，化合物2a，2b和2f是最有效的衍生物，其IC 50值可与阿司匹林作为标准药物相比。结构-活性关系的分析表明，随着吲哚N  -1上取代基的增加，抗血小板活性降低，因此表明该位置的位阻在被测化合物的活性中起主要作用。
• Identification of novel thiadiazoloacrylamide analogues as inhibitors of dengue-2 virus NS2B/NS3 protease
  作者：Hailong Liu、Ruoming Wu、Yanyan Sun、Yan Ye、Jing Chen、Xiaomin Luo、Xu Shen、Hong Liu

  DOI：10.1016/j.bmc.2014.09.057

  日期：2014.11

  Dengue virus is endemic throughout tropical and subtropical regions, and cause severe epidemic diseases. The NS2B/NS3 protease is a promising drug target for dengue virus. Herein, we report the discovery and modification of a novel class of thiadiazoloacrylamide derivatives with potent inhibitory activity against the NS2B/NS3 protease. Thiadiazolopyrimidinone 1 was firstly determined as a new chemical structure against NS2B/NS3 from a commercial compound library. Then, we sought to identify similar compounds with the thiadiazoloacrylamide core that would exhibit better activity. A series of analogues were synthesized and fourteen of them were identified with strong inhibitory activities, in which the nitrile group in the linker part was discovered as an essential group for the inhibitory activity. The best of these (8b) demonstrated an IC50 at 2.24 mu M based on in vitro DENV2 NS2B-NS3pro assays. (C) 2014 Published by Elsevier Ltd.
• Synthesis and antimicrobial activities of new thiosemicarbazones and thiazolidinones in indole series
  作者：Abdelmadjid Benmohammed、Nawel Rekiba、Yassine Sehanine、Ahmed Amine Louail、Omar Khoumeri、Mokhtaria Kadiri、Ayada Djafri、Thierry Terme、Patrice Vanelle

  DOI：10.1007/s00706-021-02823-6

  日期：2021.8

  Abstract New thiosemicarbazones were synthesized in excellent yield reaction of indole derivatives with thiosemicarbazides. These thiosemicarbazones were reacted with ethyl bromoacetate to produce original heterocyclic-substituted indole derivatives possessing a 4-oxo-thiazolidine group. Analytical IR and NMR spectra and elemental analysis were performed to reveal their structures. The antimicrobial

  摘要 在吲哚衍生物与缩氨基硫脲的极好产率反应中合成了新的缩氨基硫脲。这些缩氨基硫脲与溴乙酸乙酯反应生成具有4-氧代-噻唑烷基团的原始杂环取代吲哚衍生物。进行分析IR和NMR光谱以及元素分析以揭示它们的结构。对所有合成化合物的抗菌活性进行了体外抗革兰氏阳性菌和革兰氏阴性菌的抗菌活性评估。抗菌筛选数据显示两种化合物对金黄色葡萄球菌、大肠杆菌和铜绿假单胞菌具有活性。. 这些初步结果表明，这些新合成的化合物中的一些显示出有希望的抗菌效力。 图形摘要