3-(2,5-diphenylfuran-3-yl)-1H-indole | 1198214-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-(2,5-diphenylfuran-3-yl)-1H-indole
• CAS: 1198214-11-7
• 化学式: C₂₄H₁₇NO
• 分子量: 335.405
• InChiKey: VMUYXOWJPPGBBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(1H-indol-3-yl)-1,4-diphenylbutane-1,4-dione 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以82%的产率得到3-(2,5-diphenylfuran-3-yl)-1H-indole
  参考文献：
  名称：

  Indirect regioselective heteroarylation of indoles through a Friedel–Crafts reaction with (E)-1,4-diaryl-2-buten-1,4-diones

  摘要：

  A two-step synthesis of 3-heteroaryl indoles has been developed. The first step of the sequence involves a Friedel-Crafts alkylation of indoles with 1,4-diaryl-2-buten-1,4-diones to give the corresponding indoles bearing a 1,4-dicarbonyl moiety. The reaction is catalyzed by InCl3 and takes place with good yields. Cyclization of the diones under different Paal-Knorr conditions allows to prepare indoles substituted at the C3 position with 3-furanyl, 3-pyrrolyl- and 3-thienyl moieties. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.011

文献信息

• Establishment of atropisomerism in 3-indolyl furanoids: a synthetic, experimental and theoretical perspective
  作者：Sourav Chatterjee、Pinaki Bhattacharjee、Glenn L. Butterfoss、Anushree Achari、Parasuraman Jaisankar

  DOI：10.1039/c9ra05350f

  日期：——

  A number of axially chiral 3-indolyl furanoids have been synthesized and the individual enantiomers are found to be configurationally stable and isolable at room temperature.

  已经合成了一些轴手性的3-吲哚基呋喃衍生物，并且发现各个对映体在室温下具有构型稳定性并且可以分离。
• Newly Synthesized 3-Indolyl Furanoid Inhibits Matrix Metalloproteinase-9 Activity and Prevents Nonsteroidal Anti-inflammatory Drug-Induced Gastric Ulceration
  作者：Deep Sankar Rudra、Sourav Chatterjee、Uttam Pal、Madhumita Mandal、Susri Ray Chaudhuri、Mrinmay Bhunia、Nakul Chandra Maiti、Shila Elizabeth Besra、Parasuraman Jaisankar、Snehasikta Swarnakar

  DOI：10.1021/acs.jmedchem.3c00511

  日期：2023.7.13

  Indomethacin, a known nonsteroidal anti-inflammatory drug (NSAID) induces gastric inflammation, causing degradation of the extracellular matrix by specific matrix metalloproteinases (MMPs). We investigated the antiulcer efficacy of 3-indolyl furanoids (3g and 3c, i.e., methoxy substitution at 4- and 5-positions of the indole ring, respectively), derived from indomethacin. Interestingly, 3g protected

  吲哚美辛是一种已知的非甾体类抗炎药 (NSAID)，它会诱发胃部炎症，导致特定基质金属蛋白酶 (MMP) 降解细胞外基质。我们研究了源自吲哚美辛的 3-吲哚基呋喃类化合物（3g和3c，即分别在吲哚环的 4 位和 5 位上进行甲氧基取代）的抗溃疡功效。有趣的是，3g通过抑制 MMP-9 来预防体内吲哚美辛诱发的胃病。我们的工作制定了化学修饰策略，以开发更安全的非甾体抗炎药。此外，体外和计算机研究证实，3g通过与 MMP-9 的催化裂隙结合，抑制 MMP-9 活性，IC 50值为 50 μM，从而预防溃疡。药代动力学以大鼠血浆中的平均浓度-时间曲线表示，提取效率大于 70%，处理6.0 小时 ( t max ) 后的C max为 104.48 μg/mL ，半衰期和面积均在曲线分别为 7.0 h 和 1273.8 h μg/mL，表明3g的抗溃疡效力较高。
• 3-indolyl furanoids as inhibitors of matrix metalloproteinase-9 for prevention of gastric ulcer and other inflammatory diseases
  申请人：Council of Scientific & Industrial Research

  公开号：US10590116B2

  公开（公告）日：2020-03-17

  Disclosed are 3-indolyl furanoid compounds which are useful as potent anti-inflammatory agents and prevent gastric ulcer by inhibiting matrix metalloproteinase-9 (MMP-9) expression in gastric mucosal layer. For example, disclosed is a compound of formula 1, wherein: R1 to R6 is selected from H, OH, CH3, OCH3, Br, Cl, Ph or o-OHC6H4, OCH2—CH═CH2, or OCH2CH2CH3, and R1 to R6 is having at least one substituent with alkyl, aryl and heteroaryl groups other than H, wherein the carbon in alkyl, aryl and heteroaryl is in the range of C1 to C8. Various embodiments relate to representative compounds of Formula 1 and method of preparation thereof. Further embodiments relates to the use of representative compounds of Formula 1 in treating diseases associated with gastric ulcer and other inflammatory diseases. A noted feature of an embodiment is the IC50 value of 50 μM of one of the 3-indolyl furanoids.

  所公开的 3-吲哚基呋喃化合物可作为强效抗炎剂，通过抑制胃粘膜层中基质金属蛋白酶-9（MMP-9）的表达来预防胃溃疡。例如，公开了式 1 的化合物、 其中R1 至 R6 选自 H、OH、CH3、O 、Br、Cl、Ph 或 o-OHC6H4、O -CH═CH2 或 O ，且 R1 至 R6 具有除 H 以外的至少一个烷基、芳基和杂芳基取代基，其中烷基、芳基和杂芳基中的碳在 C1 至 C8 范围内。各种实施方案涉及式 1 的代表性化合物及其制备方法。进一步的实施方案涉及式 1 的代表性化合物在治疗与胃溃疡有关的疾病和其它炎症性疾病中的用途。一个实施方案的显著特点是3-吲哚基呋喃化合物之一的IC50值为50μM。