1-pentyl-1H-indole-3-carbaldehyde | 128600-72-6

• 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-pentyl-1H-indole-3-carbaldehyde
• 英文别名: 1-pentylindole-3-carbaldehyde
• CAS: 128600-72-6
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: UBFRFOWQRHRMHL-UHFFFAOYSA-N

物化性质

• 沸点：
  365.4±15.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-pentyl-1H-indole-3-carbaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 14.75h， 生成 (+/-)-1-(1-n-amylindol-3-yl)-2-aminopropane
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016
• 作为产物：
  描述：

  3-(N,N-dimethylaminomethyl)-N-pentylindole 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 氧气 、 苯甲酸 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以35%的产率得到1-pentyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  可见光介导的 3-(N,N-二甲基氨基甲基)-吲哚α-氧化成醛

  摘要：

  结果：我们使用光氧化还原系统（方案 1）开发了一种可见光介导的吲哚叔胺氧化成相应的醛类。基于Stern-Volmer图，提出了一系列淬火实验机理。上述方法可以获得吲哚醛衍生物，可用于合成具有生物活性特性的天然化合物，如 (-)-Vincorine。 [3]

  DOI：

  10.1002/ejoc.201801335

文献信息

• Catalyst- and Substituent-Controlled Regio- and Stereoselective Synthesis of Indolyl Acrylates by Lewis-Acid-Catalyzed Direct Functionalization of 3-Formylindoles with Diazo Esters
  作者：Sana Jamshaid、Shreedhar Devkota、Yong Rok Lee

  DOI：10.1021/acs.orglett.1c00277

  日期：2021.3.19

  A facile and efficient In(OTf)3- and BF3·OEt2-catalyzed direct transformation of 3-formylindoles with diazo esters has been developed for synthesizing diverse and functionalized indolyl acrylates. This one-pot protocol furnishes various (Z)-α-hydroxy-β-indolyl acrylates, (E)-β-(2-alkoxy-2-oxoethoxy)-α-indolyl acrylates, and (Z)-3-hydroxy-2-indolyl acrylates by a catalyst- and substituent-controlled

  已开发了一种重氮化合物，可以轻松，高效地用In（OTf）3-和BF 3 ·OEt 2催化3-甲酰基吲哚的直接转化，以合成各种功能化的丙烯酸吲哚酯。此一锅操作方案可提供各种（Z）-α-羟基-β-吲哚基丙烯酸酯，（E）-β-（2-烷氧基-2-氧代乙氧基）-α-吲哚基丙烯酸酯和（Z）-3-羟基-丙烯酸酯丙烯酸2-吲哚基酯通过催化剂和取代基控制的区域和立体选择性级联反应。该方案具有几个优点，包括催化剂的低负载，温和的反应条件，范围宽和官能团耐受性高。合成的化合物可以进一步转化为多种功能化的材料。
• 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。
• Detection of Synthetic Cannabinoids
  申请人：Benchikh Elouard

  公开号：US20120208213A1

  公开（公告）日：2012-08-16

  The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and CP families. Unique antibodies derived from novel immunogens enable said methods and kits.

  这项发明描述了检测和确定JWH和CP家族当前和未来合成大麻素的方法和试剂盒。源自新型免疫原的独特抗体使这些方法和试剂盒得以实现。
• Synthesis and Antimycobacterial Activity of Novel Thiadiazolylhydrazones of 1-Substituted Indole-3-carboxaldehydes
  作者：Kamaleddin Haj Mohammad Ebrahim Tehrani、Vida Mashayekhi、Parisa Azerang、Soroush Sardari、Farzad Kobarfard、Kobra Rostamizadeh

  DOI：10.1111/cbdd.12230

  日期：2014.2

  derivatives were tested for their antimycobacterial activity against Mycobacterium bovis BCG, and the results revealed that among the synthesized compounds, thiadiazole derivatives 4e, 4f, 4n, 4p, 4q, and 4t exhibited the highest activity with IC50 value of 3.91 μg/mL. The results indicate that the thiadiazole moiety plays a vital role in exerting antimycobacterial activity.

  制备了一系列新的取代吲哚的硫代碳氢azo及其相应的噻二唑衍生物，并通过不同的分析和光谱方法证实了它们的结构。通过顺序合成策略制备衍生物，包括在吲哚环的N -1位被各种脂族和苄基取代基取代，然后与硫代碳酰肼缩合，最后由原甲酸三乙酯环化。测试了这些衍生物对牛分枝杆菌BCG的抗分枝杆菌活性，结果表明，在合成的化合物中，噻二唑衍生物4e，4f，4n，4p，4q和4t表现出最高的活性，IC 50值为3.91μg/ mL。结果表明，噻二唑部分在发挥抗分枝杆菌活性中起着至关重要的作用。
• Ruthenium(<scp>ii</scp>)-catalyzed regioselective direct C4- and C5-diamidation of indoles and mechanistic studies
  作者：Shreedhar Devkota、Suyeon Kim、Seok Yeol Yoo、Sonaimuthu Mohandoss、Mu-Hyun Baik、Yong Rok Lee

  DOI：10.1039/d1sc02138a

  日期：——

  at the C4- and C5-positions using various dioxazolones is described. This novel protocol allows for the effective installation of two amide groups on the benzene ring in indole. A remarkably broad substrate scope, excellent functional group tolerance, and mild reaction conditions are notable features of this protocol. Further explorations reveal that benzo[b]thiophene-3-carboxaldehyde is a viable substrate

  描述了使用各种二恶唑酮在 C4 和 C5 位进行钌 ( II ) 催化的区域选择性直接二酰胺化 3-羰基吲哚。这种新颖的协议允许在吲哚的苯环上有效安装两个酰胺基团。非常广泛的底物范围、优异的官能团耐受性和温和的反应条件是该协议的显着特点。进一步的探索表明苯并[ b]噻吩-3-甲醛是一种可行的底物，并提供其相应的二酰胺化产物。二酰氨基吲哚进一步转化为各种功能化产品，用作金属离子检测的传感器。还进行了密度泛函理论研究以提出反应机制并提供对反应中观察到的区域选择性的详细理解。