2-(indol-3-yl)acetylfuran

• 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-(indol-3-yl)acetylfuran
• 英文别名: 1-(2-furanyl)-2-(3-indolyl)ethanone；1-(furan-2-yl)-2-(1H-indol-3-yl)ethanone
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: CRTZFZFRUQDYBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-C-(indol-3-yl)methyl-α-L-xylo-hex-3-ulofuranosonic acid 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以45%的产率得到2-hydroxy-3-(indol-3-yl)-4-hydroxymethylcyclopent-2-enone
  参考文献：
  名称：

  摘要：

  Transformation of ascorbigen in an acidic medium, which affects the carbohydrate moiety of the molecule and results in the formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone, 5-hydroxymethyl-2-(indol-3-yl)methylidenetetrahydrofuran-3-one, and 2-(indol-3-yl)acetylfuran, was investigated. Isolation and identification of the intermediates allowed the elucidation of the mechanism of this domino-type reaction.

  DOI：

  10.1023/a:1014087630107

文献信息

• ARYL HYDROCARBON RECEPTOR MODULATOR
  申请人：Ariagen, Inc.

  公开号：US20190307731A1

  公开（公告）日：2019-10-10

  Disclosed is an aryl hydrocarbon receptor modulator of formula (I), and a pharmaceutically acceptable salt thereof, wherein R′ is H, CN, CH 2 (OH)R 0 , C m H 2m+1 , C n H 2n-1 , C n H 2n-3 , two R a are independently H or two R a together form ═O or ═N—W 3 —R 1 ; A is a C 6 to C 10 aromatic ring unsubstituted or substituted with 1 to 3 R, or a C 2 -C 10 heteroaromatic ring interrupted by 1 to 5 heteroatoms selected from N, O, and S or a 4 to 7 membered nonaromatic heterocyclic ring containing C═N and interrupted by 1 to 3 heteroatoms selected from N, O, and S, with either one unsubstituted or substituted with 1 to 3 R; Q is R, or is a C 6 to C 10 aromatic ring or a C 2 to C 10 heteroaromatic ring unsubstituted or substituted with 1 to 3 R and interrupted by 1 to 5 heteroatoms selected from N, O, and S; and R is R c which is C-attached or R N which is N-attached. The compounds of formula (I) of the present invention can regulate AhR activity, and can be used to inhibit the growth of cancer cells and inhibit the metastasis and invasion of tumor cells.

  本发明揭示了一种化学式（I）的芳香烃受体调节剂及其药用可接受盐，其中R′为H、CN、CH2（OH）R0、CmH2m+1、CnH2n-1、CnH2n-3，两个Ra独立地为H或两个Ra共同形成═O或═N—W3—R1；A为未取代或取代1至3个R的C6至C10芳香环，或由N、O和S中选择的1至5个杂原子中断的C2-C10杂芳环，或含有C═N并由N、O和S中选择的1至3个杂原子中断的4至7个成员的非芳杂环，其中一个未取代或取代1至3个R；Q为R，或者是未取代或取代1至3个R并由N、O和S中断的C6至C10芳香环或C2至C10杂芳环；R为C-连接的Rc或N-连接的RN。本发明的化合物可以调节AhR活性，可用于抑制癌细胞的生长，以及抑制肿瘤细胞的转移和侵袭。
• Plant components and extracts and uses thereof
  申请人：G.I.M.-GESELLSCHAFT FÜR INNOVATIVE MEDIZIN GMBH NFG OHG

  公开号：EP1842541A1

  公开（公告）日：2007-10-10

  The present invention provides a medicament comprising a chemical compound according to formula 1: wherein R1 is hydrogen, fluorine or methoxy, R2 is hydrogen, methyl, ethyl, propyl or fluorine and R3 is furanyl or pyranyl, and its use for the activation of the aryl hydrocarbon receptor, as well as the use of a plant extract or plant juice for the production of a preparation for the activation of the aryl hydrocarbon receptor.

  本发明提供了一种包含根据式 1 所列化合物的药物： 其中 R1 是氢、氟或甲氧基，R2 是氢、甲基、乙基、丙基或氟，R3 是呋喃基或吡喃基，其用途是激活芳基烃受体，以及使用植物提取物或植物汁液生产激活芳基烃受体的制剂。
• MEDICAMENT, COSMETIC OR FOOD PRODUCT COMPRISING AN INDOL COMPOUND, THE USE THEREOF AND THE METHOD OF ISOLATION THEREOF FROM SAUERKRAUT
  申请人：G.I.M.-GESELLSCHAFT FÜR INNOVATIVE MEDIZIN G.M.B.H. NFG OHG

  公开号：EP2004179A1

  公开（公告）日：2008-12-24
• Plant Components and Extracts and Uses Thereof
  申请人：Jungbauer Alois

  公开号：US20090182028A1

  公开（公告）日：2009-07-16

  The present invention provides a medicament comprising a chemical compound according to formula A: wherein R1 is hydrogen, fluorine, chlorine, bromine, hydroxy, mercapto, methoxy, ethoxy, acetoxy, methyl, ethyl, propyl, isopropyl, t-butyl, nitro, amin, N,N-dimethylaminoyl, N,N-diethyl-aminoyl; R2 is hydrogen, a C 1-8 -alkyl e.g. methyl, ethyl, propyl, isopropyl, butyl, t-butyl; an C 1-8 -acyl e.g. acetyl, propionyl; R3 is a C 5-12 -heterocyclic ring, e.g. furanyl, pyranyl, pyrrolyl, pyridinyl, pyrazolyl, thienyl, thiazolyl, indolyl or -0R4 ; R4 is a C 5 -C 12 -aromatic ring e.g. phenyl; unsubstituted or substituted in any position with fluorine, chlorine, bromine, methoxy, ethoxy, C 1-8 -carboxy; Z is OH or 0; and n is 0, 1, 2 or 3, and m is 0, 1, 2 or 3, and its use for the activation of the aryl hydro carbon receptor.
• ARYL HYDROCARBON RECEPTOR MODULATORS
  申请人：SHENZHEN IMMUNOVA PHARMACEUTICAL CO., LTD.

  公开号：US20190330201A1

  公开（公告）日：2019-10-31

  The disclosure discloses an aryl hydrocarbon receptor modulators of formula (I), and pharmaceutically acceptable salts, R′ is H, CN, CH 2 (OH)R 0 , C m H 2m+1 , C n H 2n-1 , C n H 2n-3 , two R a is independently H, or two R a together form ═O or ═N—W 3 —R 1 ; A is a C 6 to C 10 aromatic ring, or a C 2 to C 10 heteroaromatic ring containing 1 to 5 heteroatom from N, O and S, or 4 to 7 membered non-aromatic heterocyclic ring containing 1 to 3 heteroatom from N, O and S and C═N, which are with no substituent or substituted by 1 or 3 R; Q is R, or a C 6 to C 10 aromatic ring or a C 2 to C 10 heteroaromatic ring containing 1 to 5 heteroatom selected from N, O and S, which are with no substituent or substituted by 1 or 3 R; R is R c connected with C or R N connected with N.