1-异丁基-1H-吲哚-3-甲醛 | 433254-46-7

• 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
• 中文名称: 1-异丁基-1H-吲哚-3-甲醛
• 英文名称: N-(2-methylpropyl)-indole-3-carboxaldehyde
• 英文别名: 1-isobutyl-1H-indole-3-carbaldehyde；1-(2-methylpropyl)indole-3-carbaldehyde
• CAS: 433254-46-7
• 化学式: C₁₃H₁₅NO
• mdl: MFCD03145662
• 分子量: 201.268
• InChiKey: FYPAEEAXXGSBFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-异丁基-1H-吲哚-3-甲醛 在 吡啶 、 四丁基氟化铵 、 甲基磺酰氯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E)-(2-(hydroxymethyl)-4-((1-isobutyl-1H-indol-3-yl)methylene)-5-oxotetrahydrofuran-2-yl)methyl pivalate
  参考文献：
  名称：

  α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands

  摘要：

  Diacylglycerol-lactones have proven to be a powerful template for the design of potent ligands targeting CI domains, the recognition motif for the cellular second messenger diacylglycerol. A major objective has been to better understand the structure activity relations distinguishing the seven families of signaling proteins that contain such domains, of which the protein kinase C (PKC) and RasGRP families are of particular interest. Here, we synthesize a series of aryl- and alkyl-substituted diacylglycerol-lactones and probe their relative selectivities for RasGRP3 versus PKC. Compound 96 showed 73-fold selectivity relative to PKC alpha 45 and 45-fold selectivity relative to PKC epsilon for in vitro binding activity. Likewise, in intact cells, compound 96 induced Ras activation, a downstream response to RasGRP stimulation, with 8-29 fold selectivity relative to PKC delta S299 phosphorylation, a measure of PKC delta stimulation.

  DOI：

  10.1021/acs.jmedchem.8b00661
• 作为产物：
  描述：

  3-吲哚甲醛 、 溴代异丁烷 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 以93.3%的产率得到1-异丁基-1H-吲哚-3-甲醛
  参考文献：
  名称：

  Mechanofluorochromic properties of fluorescent molecules based on a dicyanomethylene-4H-pyran and indole isomer containing different alkyl chains via an alkene module

  摘要：

  烷基链的长度和异构化对二氰甲烯基-4H-吡喃衍生物的机械荧光性能产生不同影响，当吲哚单元的取代位置不同时。

  DOI：

  10.1039/c7ra06951k

文献信息

• 二氰基亚甲基-4H-吡喃衍生物及其制备方法 与用途
  申请人：温州大学

  公开号：CN107382982B

  公开（公告）日：2020-07-31

  本发明具体涉及二氰基亚甲基‑4H‑吡喃衍生物及其制备方法与用途。二氰基亚甲基‑4H‑吡喃衍生物的制备方法，包括(1)以2,6‑二甲基‑4‑吡喃酮1为起始原料，与丙二腈发生加成‑消除反应得到中间体2；(2)中间体2与带有不同烷基链的吲哚醛发生加成‑消除反应，得到二氰基亚甲基‑4H‑吡喃衍生物。本发明把带有不同烷基的吲哚结构单元和二氰基亚甲基‑4H‑吡喃结构单元引入到有机固体发光材料领域，开发出一些新型压致发光变色材料，在光电领域将具有重要的应用。本发明提出的方法，合成工艺简单，纯化容易，所合成的压致发光材料非常适用于制备压力传感器、防伪商标等多个领域，具有良好的科研价值和工业化应用潜力。
• Information-Rich, Dual-Function ¹³C/²H-Isotopic Crosstalk NMR Assay for Human Serine Racemase (hSR) Provides a PLP-Enzyme “Partitioning Fingerprint” and Reveals Disparate Chemotypes for hSR Inhibition
  作者：Stephany M. Ramos de Dios、Jared L. Hass、Danielle L. Graham、Nivesh Kumar、Aina E. Antony、Martha D. Morton、David B. Berkowitz

  DOI：10.1021/jacs.2c12774

  日期：2023.2.8

  deployed to screen a 1020-compound library and identifies an indolo-chroman-2,4-dione inhibitor family that displays allosteric site binding behavior (noncompetitive inhibition vs l-Ser substrate; competitive inhibition vs adenosine 5′-triphosphate (ATP)). This assay also reveals important mechanistic information for hSR; namely, that H/D exchange is ∼13-fold faster than racemization, implying that K56 protonates

  报道了第一个针对人类丝氨酸消旋酶 (hSR) 的双功能测定，hSR 是人类生物学中唯一真正的消旋酶。 hSR 外消旋功能对于神经元信号传导至关重要，因为产物d-丝氨酸 ( d -Ser) 是一种有效的N-甲基d-天冬氨酸 (NMDA) 共激动剂，对于学习和记忆很重要，但d -Ser 信号传导功能失调在某些神经元疾病中观察到。 hSR 的第二个功能是 β-消除并产生丙酮酸；这种活性在结直肠癌中升高。这种新的基于 NMR 的测定允许人们仅使用天然l -Ser 底物和 hSR 来监测 α-质子交换化学和 β-消除，并且是此类测定中最灵敏的。该测定明智地采用了分离的双13 C 标记和13 C/ 2 H 串扰，利用了氘的分裂和屏蔽效应。该测定用于筛选 1020 个化合物库，并鉴定显示变构位点结合行为的吲哚色满-2,4-二酮抑制剂家族（非竞争性抑制与l -Ser 底物；竞争性抑制与腺苷 5'-三磷酸 (ATP)
• B-ring modified aurones as promising allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase
  作者：Amel Meguellati、Abdelhakim Ahmed-Belkacem、Wei Yi、Romain Haudecoeur、Marie Crouillère、Rozenn Brillet、Jean-Michel Pawlotsky、Ahcène Boumendjel、Marine Peuchmaur

  DOI：10.1016/j.ejmech.2014.04.005

  日期：2014.6

  Following our recent report showing the potential of naturally occurring aurones (2-benzylidenebenzofuran-3(2H)-ones) as anti-hepatitis C virus (HCV) agents, efforts were continued in order to refine the structural requirements for the inhibitory effect on HCV RNA-dependent RNA polymerase (RdRp). In this study, we targeted the B-ring moiety of aurones with the aim to improve structural features associated with higher inhibition of the targeted polymerase. In vitro evaluation of the RdRp inhibitory activity of the 37 newly synthesized compounds pointed out that the replacement of the B-ring with an N-substituted indole moiety induced the highest inhibitory effect. Of these, compounds 31, 40 and 41 were found to be the most active (IC50 = 2.3-2.4 μM). Docking experiments performed with the most active compounds revealed that the allosteric thumb pocket I of RdRp is the binding pocket for aurone analogues.
• Mechanofluorochromic properties of fluorescent molecules based on a dicyanomethylene-4H-pyran and indole isomer containing different alkyl chains via an alkene module
  作者：Lebin Qian、Yibin Zhou、Miaochang Liu、Xiaobo Huang、Ge Wu、Wenxia Gao、Jinchang Ding、Huayue Wu

  DOI：10.1039/c7ra06951k

  日期：——

  The length and isomerization of the alkyl chains exhibit different effects on the mechanofluorochromic properties of the dicyanomethylene-4H-pyran derivatives when the substitution position of the indole unit is different.

  烷基链的长度和异构化对二氰甲烯基-4H-吡喃衍生物的机械荧光性能产生不同影响，当吲哚单元的取代位置不同时。
• α-Arylidene Diacylglycerol-Lactones (DAG-Lactones) as Selective Ras Guanine-Releasing Protein 3 (RasGRP3) Ligands
  作者：Jihyae Ann、Agnes Czikora、Amandeep S. Saini、Xiaoling Zhou、Gary A. Mitchell、Nancy E. Lewin、Megan L. Peach、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1021/acs.jmedchem.8b00661

  日期：2018.7.26

  Diacylglycerol-lactones have proven to be a powerful template for the design of potent ligands targeting CI domains, the recognition motif for the cellular second messenger diacylglycerol. A major objective has been to better understand the structure activity relations distinguishing the seven families of signaling proteins that contain such domains, of which the protein kinase C (PKC) and RasGRP families are of particular interest. Here, we synthesize a series of aryl- and alkyl-substituted diacylglycerol-lactones and probe their relative selectivities for RasGRP3 versus PKC. Compound 96 showed 73-fold selectivity relative to PKC alpha 45 and 45-fold selectivity relative to PKC epsilon for in vitro binding activity. Likewise, in intact cells, compound 96 induced Ras activation, a downstream response to RasGRP stimulation, with 8-29 fold selectivity relative to PKC delta S299 phosphorylation, a measure of PKC delta stimulation.