2-(1H-1,2,4-triazol-1-yl)-1H-indole | 1414867-87-0

• 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: 2-(1H-1,2,4-triazol-1-yl)-1H-indole
• 英文别名: 2-[1,2,4]-triazol-1-yl-1H-indole；2-(1,2,4-triazol-1-yl)-1H-indole
• CAS: 1414867-87-0
• 化学式: C₁₀H₈N₄
• 分子量: 184.2
• InChiKey: AYTHPLVIKQLNNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1H-1,2,4-triazol-1-yl)-1H-indole 、 bis(3,4,5-trimethoxyphenyl)disulfide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1,2,4-triazol-1-yl)-3-(3,4,5-trimethoxyphenyl)sulfanyl-1H-indole
  参考文献：
  名称：

  吲哚的需氧氧化C–H偶氮化和黄素-碘偶联的有机催化一锅法合成氮唑基硫吲哚

  摘要：

  已开发了由黄素-碘偶联的有机催化驱动的吲哚与唑类的需氧氧化交叉偶联，用于2-（azol-1-yl）吲哚的绿色合成。偶联的有机催化系统通过利用分子氧作为唯一的牺牲试剂，以原子经济的方式从吲哚，唑类和硫醇一锅法合成2-偶氮基-3-硫代吲哚。

  DOI：

  10.1021/acs.orglett.1c00241
• 作为产物：
  描述：

  吲哚 在 正丁基锂 作用下， 生成 2-(1H-1,2,4-triazol-1-yl)-1H-indole
  参考文献：
  名称：

  吲哚的需氧氧化C–H偶氮化和黄素-碘偶联的有机催化一锅法合成氮唑基硫吲哚

  摘要：

  已开发了由黄素-碘偶联的有机催化驱动的吲哚与唑类的需氧氧化交叉偶联，用于2-（azol-1-yl）吲哚的绿色合成。偶联的有机催化系统通过利用分子氧作为唯一的牺牲试剂，以原子经济的方式从吲哚，唑类和硫醇一锅法合成2-偶氮基-3-硫代吲哚。

  DOI：

  10.1021/acs.orglett.1c00241

文献信息

• Bis(2-cycloazylindolyl)titanium Complexes: Synthesis, Characterization, and the Catalytic Behaviors towards Hydroamination and Ring-opening Polymerization of ϵ-Caprolactone
  作者：Jing-Jing Zhao、Hao Pei、Yan-Mei Chen、Ning Lu、Jin-Na Liu、Jin-Fa Hu、Wei Liu、Wu Li、Yahong Li

  DOI：10.1002/zaac.201500072

  日期：2015.6

  corresponding complexes Ti(L1)2(NMe2)2 (1) and Ti(L2)2(NMe2)2 (2), respectively. The titanium complexes were fully characterized by NMR measurement and elemental analysis as well as the single-crystal X-ray diffraction of 1 and 2. Both 1 and 2 exhibit high activities towards intermolecular hydroamination of terminal alkynes with high selectivity, and they also efficiently promote the ring-opening polymerization

  配体 2-pyrazol-1-yl-1H-indole (HL1) 和 2-1,2,4-triazol-1-yl-1H-indole (HL2) 在四氢呋喃中分别与 Ti(NMe2)4 反应形成相应的配合物分别为 Ti(L1)2(NMe2)2 (1) 和 Ti(L2)2(NMe2)2 (2)。钛配合物通过 NMR 测量和元素分析以及 1 和 2 的单晶 X 射线衍射进行了充分表征。 1 和 2 均表现出高选择性对末端炔烃的分子间加氢胺化的高活性，并且它们也有效地促进ε-己内酯的开环聚合。
• Iodine-Catalyzed Oxidative Cross-Coupling of Indoles and Azoles: Regioselective Synthesis of <i>N</i>-Linked 2-(Azol-1-yl)indole Derivatives
  作者：Danupat Beukeaw、Kwanchanok Udomsasporn、Sirilata Yotphan

  DOI：10.1021/jo502933e

  日期：2015.4.3

  A highly efficient iodine-catalyzed regioselective oxidative cross-coupling of an indole C-H bond and azole N-H bond is described. This metal-free reaction can be easily carried out at room temperature under mild and environmentally friendly conditions and provides a series of N-linked 2-(azol-1-yl)indole derivatives in moderate to excellence yields.
• Toward Highly Potent Cancer Agents by Modulating the C-2 Group of the Arylthioindole Class of Tubulin Polymerization Inhibitors
  作者：Giuseppe La Regina、Ruoli Bai、Whilelmina Maria Rensen、Erica Di Cesare、Antonio Coluccia、Francesco Piscitelli、Valeria Famiglini、Alessia Reggio、Marianna Nalli、Sveva Pelliccia、Eleonora Da Pozzo、Barbara Costa、Ilaria Granata、Amalia Porta、Bruno Maresca、Alessandra Soriani、Maria Luisa Iannitto、Angela Santoni、Junjie Li、Marlein Miranda Cona、Feng Chen、Yicheng Ni、Andrea Brancale、Giulio Dondio、Stefania Vultaggio、Mario Varasi、Ciro Mercurio、Claudia Martini、Ernest Hamel、Patrizia Lavia、Ettore Novellino、Romano Silvestri

  DOI：10.1021/jm3013097

  日期：2013.1.10

  New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized S. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCl/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.
• Highly Regioselective C–N Bond Formation through C–H Azolation of Indoles Promoted by Iodine in Aqueous Media
  作者：Wen-Bin Wu、Jing-Mei Huang

  DOI：10.1021/ol302609m

  日期：2012.12.7

  An efficient and metal-free method for the direct C-N coupling of indoles with azoles to produce 2-(azol-1-yl)indoles in aqueous solution has been developed. This reaction proceeded highly regioselectively to provide a variety of indole derivatives with good to excellent yields.
• NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：Ardea Biosciences, Inc.

  公开号：EP1545483B1

  公开（公告）日：2011-04-06