1-(pent-4-en-1-yl)-1H-indole-3-carboxylic acid | 1379081-26-1

• 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: 1-(pent-4-en-1-yl)-1H-indole-3-carboxylic acid
• 英文别名: 1-Pent-4-enylindole-3-carboxylic acid
• CAS: 1379081-26-1
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: IDLFWIOLQCNTKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(pent-4-en-1-yl)-1H-indole-3-carboxylic acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 (p-cymene)ruthenium(II) chloride 、 palladium on activated charcoal 、 氢气 、 碘 、 氧气 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 50.0h， 生成 methyl 2-(10-(4-chlorophenylthio)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate
  参考文献：
  名称：

  介质中钌催化的脱羧CHH烯基化反应：四氢吡啶并吲哚的合成

  摘要：

  我们在本文中公开了在水溶液中具有宽的底物范围的N-取代的吲哚基羧酸的Ru（II）催化的脱羧和氧化偶联。该方法为在温和条件下合成各种吲哚稠合的环己基乙酸提供了一种可持续而有效的途径。

  DOI：

  10.1021/acs.joc.8b00229
• 作为产物：
  描述：

  5-溴-1-戊烯 在 sodium hydride 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(pent-4-en-1-yl)-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Rh(iii)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C–H activation

  摘要：

  生物学上引人关注的融合多环内酰胺已通过一种分子内氧化还原中性环化过程制备。通过适当选择带有多种侧链烯烃的底物，可以激活并功能化较不利的C-H键。这种C-H键的活化在温和条件下进行，无需外部氧化剂，并且对取代基具有广泛的适用性。

  DOI：

  10.1039/c4cc00029c

文献信息

• Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation
  作者：Elizabeth L. Glaisyer、Michael S. Watt、Kevin I. Booker-Milburn

  DOI：10.1021/acs.orglett.8b02543

  日期：2018.9.21

  A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C–H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated

  报道了一种新的Pd（II）催化的级联序列，用于从简单的起始原料形成多杂环。该序列适用于吲哚和吡咯底物，并且可以接受一定范围的取代基。该反应被认为是通过Pd（II）催化的C–H活化的Heck反应进行的，然后是第二个Pd（II）催化的aza-Wacker反应，每个序列有两个Cu（II）介导的Pd（0）转换。该序列可以被认为是正式的[4 + 2]杂环化。
• Excited‐State Copper Catalysis for the Synthesis of Heterocycles
  作者：Arghya Banerjee、Satavisha Sarkar、Jagrut A. Shah、Nicoline C. Frederiks、Emmanuel A. Bazan‐Bergamino、Christopher J. Johnson、Ming‐Yu Ngai

  DOI：10.1002/anie.202113841

  日期：2022.1.21

  Visible-light-induced excited-state copper catalysis enables the synthesis of more than 10 distinct classes of heterocycles. The reaction tolerates a broad array of functional groups and complex molecular scaffolds, including derivatives of peptides, natural products, and marketed drugs.

  可见光诱导的激发态铜催化能够合成 10 多种不同类别的杂环化合物。该反应可耐受多种官能团和复杂的分子支架，包括肽衍生物、天然产物和市售药物。
• Synthesis and <i>in Vitro</i> Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA
  作者：Annelies Cannaert、Eric Sparkes、Edward Pike、Jia Lin Luo、Ada Fang、Richard C. Kevin、Ross Ellison、Roy Gerona、Samuel D. Banister、Christophe P. Stove

  DOI：10.1021/acschemneuro.0c00644

  日期：2020.12.16

  Synthetic cannabinoid receptor agonists (SCRAs) are an evolving class of new psychoactive substances (NPS) with structurally diverse compounds emerging each year. Due to the rapid pace at which these drugs enter the market, there is often little or nil information regarding the pharmacology of these substances despite widespread human use. In this study, 12 recently emerged SCRAs (reported between 2018 and 2020) were synthesized, analytically characterized, and pharmacologically evaluated using a live cell-based nanoluciferase complementation reporter assay that monitors in vitro cannabinoid receptor type 1 (CB1) activation via its interaction with β-arrestin 2 (βarr2). All synthesized SCRAs acted as agonists of CB1, although differences in potency (EC50 = 2.33-5475 nM) and efficacy (Emax = 37-378%) were noted, and several structure-activity relationships were identified. SCRAs featuring indazole cores (EC50 = 2.33-159 nM) were generally of equal or greater potency than indole analogues (EC50 = 32.9-330 nM) or 7-azaindole derivatives (EC50 = 64.0-5475 nM). Interestingly, with the exception of APP-BINACA (Emax = 75.7%) and 5F-A-P7AICA (Emax = 37.4%), all SCRAs showed greater efficacy than the historical SCRA JWH-018 to which responses were normalized (Emax = 142-378%). The most potent CB1 agonists in the study were ADB-BINACA (EC50 = 6.36 nM), 4F-MDMB-BINACA (EC50 = 7.39 nM), and MDMB-4en-PINACA (EC50 = 2.33 nM). Notably, all of these SCRAs featured an indazole core as well as a "bulky" tert-butyl moiety in the pendant amino acid side chain. This study confirms that recently detected SCRAs 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA were all able to activate the CB1 receptor in vitro, albeit to different extents, and are potentially psychoactive in vivo. These results indicate that further evaluation of these widely used NPS is warranted to better understand the risks associated with human consumption of these drugs.