3,3'-((5-methylfuran-2-yl)methylene)bis(1H-indole)

• 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: 3,3'-((5-methylfuran-2-yl)methylene)bis(1H-indole)
• 英文别名: 5-methyl-2-[bis(indol-3-yl)methyl]furane；3,3'-[(5-methylfuran-2-yl)methanediyl]bis(1H-indole)；3-[1H-indol-3-yl-(5-methylfuran-2-yl)methyl]-1H-indole
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: VQWZIPRNTRIIKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.7
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-甲基呋喃醛 、 吲哚 在 C₆₂H₅₈N₈O₂₀Y₂Zn₂ 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 3,3'-((5-methylfuran-2-yl)methylene)bis(1H-indole)
  参考文献：
  名称：

  四核3d / 4f配位簇是Friedel Crafts烷基化反应的高效催化剂

  摘要：

  首次描述了一系列定制设计的高收率等骨架四核3d / 4f配位簇，这些化合物在弗里德尔工艺烷基化反应中作为低催化负载的催化剂表现出了高效率。

  DOI：

  10.1039/c6cc03608b

文献信息

• One-pot solvent-free synthesis of triaryl- and triheteroarylmethanes by Bi(OTf)3-catalyzed Friedel-Crafts reaction of arenes/heteroarenes with trialkyl orthoformates
  作者：Surisa Tuengpanya、Chayamon Chantana、Uthaiwan Sirion、Wipada Siritanyong、Klaokwan Srisook、Jaray Jaratjaroonphong

  DOI：10.1016/j.tet.2018.05.079

  日期：2018.8

  A convenient, practical and highly efficient one-pot method has been developed for the synthesis of triaryl- and triheteroarylmethane derivatives by Bi(OTf)3-catalyzed Friedel-Crafts alkylation of trialkyl orthoformates in combination with a wide variety of arenes/heteroarenes at room temperature under solvent-free conditions and in an air atmosphere. The methodology offers an operational simplicity

  已经开发了一种方便，实用，高效的一锅法，该方法通过在室温下用Bi（OTf）3催化三烷基原甲酸酯的Friedel-Crafts烷基化与多种芳烃/杂芳烃结合来合成三芳基和三杂芳基甲烷衍生物无溶剂条件下和大气中的最高温度。该方法提供了操作简便性，高原子经济性和对环境有益的程序。此外，选择的化合物3k在抑制一氧化氮方面显示出有希望的抗炎活性，并且对巨噬细胞没有显着的细胞毒性作用。
• Practical Synthesis of Triaryl- and Triheteroarylmethanes by Reaction of Aldehydes and Activated Arenes Promoted by Gold(III) Chloride
  作者：Vijay Nair、K. G. Abhilash、N. Vidya

  DOI：10.1021/ol052423h

  日期：2005.12.1

  [reaction: see text] Electron-rich arenes condense efficiently with various aldehydes under the influence of AuCl3, thus opening up a practical route to triarylmethanes, which have important applications. The mild conditions employed are especially noteworthy.

  [反应：参见正文]在AuCl3的影响下，富电子芳烃与各种醛类有效地缩合，从而开辟了一条实用的生产三芳基甲烷的途径，这具有重要的应用前景。使用的温和条件尤其值得注意。
• Bis-Indole derivatives having antimetastatic activity, a process for their preparation and pharmaceutical compositions containing them
  申请人：Boehringer Mannheim Italia S.p.A.

  公开号：EP0887348A1

  公开（公告）日：1998-12-30

  The present invention relates to compounds of the general formula (I): wherein: R and R' are independently selected from hydrogen, hydroxy, chlorine, bromine, iodine, fluorine, (C1-C6)alkyl, (C1-C4)alkoxy, (C1-C4)acyloxy, amino, mono-(C1-C4)alkylamino, di-(C1-C4)alkylamino, -SH, (C1-C4)alkylthio, carboxy, (C1-C4)alkoxycarbonyl groups; R1 and R1' are independently selected from hydrogen, hydroxy, hydroxymethyl, amino, carboxy, (C1-C4)alkyl groups; A is a phenyl or naphtyl group substituted by at least one group selected from hydoxy, carboxy, -SH, -CONHOH or -PO3H2 group, or is a 5- or 6-membered heterocycle containing one or two heteroatoms selected from oxygen, nitrogen or sulfur, which can be optionally benzocondensed and/or substituted by at least one group selected from pyridyl, -SH, -PO3H2, carboxy or CONHOH, or is a group of formula -(CH2)n-X, in which n is zero or the integers 1 or 2, and X is selected from -SH -PO3H2, -CONHOH, carboxy, amino, mono-(C1-C4)alkylamino, di-(C1-C4)alkylamino, enantiomers, diastereoisomers, racemates and mixtures thereof, as well as salts thereof with pharmaceutically acceptable acids and bases, as antitumor and antimetastatic agents.

  本发明涉及通式（I）的化合物，其中： R和R'独立地选择氢，羟基，氯，溴，碘，氟，（C1-C6）烷基，（C1-C4）烷氧基，（C1-C4）酰氧基，氨基，单（C1-C4）烷基氨基，双（C1-C4）烷基氨基，-SH，（C1-C4）烷基硫基，羧基，（C1-C4）烷氧羰基基团； R1和R1'独立地选择氢，羟基，羟甲基，氨基，羧基，（C1-C4）烷基基团； A是苯基或萘基，被至少选择一个羟基，羧基，-SH，-CONHOH或-PO3H2基团取代，或者是一个含有一个或两个氧，氮或硫杂原子的5-或6-成员杂环，可以选择地苯并和/或被至少一个吡啶基，-SH，-PO3H2，羧基或CONHOH基团取代，或者是一个通式为-(CH2)n-X的基团，在其中n为零或整数1或2，X选择自-SH，-PO3H2，-CONHOH，羧基，氨基，单（C1-C4）烷基氨基，双（C1-C4）烷基氨基，对映异构体，顺反异构体，外消旋体和其混合物，以及其与药学上可接受的酸和碱的盐，作为抗肿瘤和抗转移剂。
• BIS-INDOLE DERIVATIVES HAVING ANTIMETASTATIC ACTIVITY, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Roche Diagnostics GmbH

  公开号：EP0991645A1

  公开（公告）日：2000-04-12
• [EN] BIS-INDOLE DERIVATIVES HAVING ANTIMETASTATIC ACTIVITY, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DERIVES DE BIS-INDOLE PRESENTANT UNE ACTIVITE ANTIMETASTASIQUE, PROCEDE POUR LEUR PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：ROCHE DIAGNOSTICS GMBH

  公开号：WO1999000381A1

  公开（公告）日：1999-01-07

  (EN) The present invention relates to compounds of general formula (I) wherein: R and R' are independently selected from hydrogen, hydroxy, chlorine, bromine, iodine, fluorine, (C1-C6)alkyl, (C1-C4)alkoxy, (C1-C4)acyloxy, amino, mono-(C1-C4)alkylamino, di-(C1-C4)alkylamino, -SH, (C1-C4)alkylthio, carboxy, (C1-C4)alkoxycarbonyl groups; R1 and R1' are independently selected from hydrogen, hydroxy, hydroxymethyl, amino, carboxy, (C1-C4)alkyl groups; A is a phenyl or naphthyl group substituted by at least one group selected from hydroxy, carboxy, -SH, -CONHOH or -PO3H2 group, or is a 5- or 6-membered heterocycle containing one or two heteroatoms selected from oxygen, nitrogen or sulfur, which can be optionally benzocondensed and/or substituted by at least one group selected from pyridyl, -SH, -PO3H2, carboxy or CONHOH, or is a group of the formula -(CH2)n-X, in which n is zero or the integers 1 or 2, and X is selected from -SH, -PO3H2, -CONHOH, carboxy, amino, mono-(C1-C4)alkylamino, di-(C1-C4)alkylamino, enantiomers, diastereoisomers, racemates and mixtures thereof, as well as salts thereof with pharmaceutically acceptable acids and bases, as antitumor and antimetastatic agents.(FR) La présente invention concerne des composés selon la formule générale (I). Dans cette dernière, R et R' sont indépendamment sélectionnés parmi des groupes hydrogène, hydroxy, chlore, brome, iode, fluor, alkyle (C1-C6), alcoxy (C1-C4), acyloxy (C1-C4), amino, mono-(C1-C4)alkylamino, di-(C1-C4)alkylamino, -SH, alkylthio(C1-C4), carboxy, alcoxycarbonyl(C1-C4). R1 et R1' sont indépendamment sélectionnés parmi des groupes hydrogène, hydroxy, hydroxyméthyle, amino, carboxy, alkyl(C1-C4); A est un groupe phényle ou naphtyle substitué par au moins un groupe sélectionné parmi des groupes hydroxy, carboxy, -SH, -CONHOH ou -PO3H2, ou est un hétérocycle à 5 ou 6 éléments contenant un ou deux hétéroatomes sélectionnés parmi de l'oxygène, azote ou soufre, qui peuvent éventuellement être benzocondensés et/ou substitués par au moins un groupe sélectionné parmi pyridyl, -SH, -PO3H2, carboxy ou CONHOH ou est un groupe présentant la formule -(CH2)n-X dans laquelle n est égal à zéro ou les nombres entiers 1 ou 2, et X est sélectionné parmi -SH, -PO3H2, -CONHOH, carboxy, amino, mono-(C1-C4)alkylamino, di-(C1-C4)alkylamino, énantiomères, diastéréoisomères, composés racémiques et mélanges de ces derniers, ainsi que des sels de ces derniers avec des acides pharmaceutiquement acceptables et des bases, comme agents antitumoraux et antimétastastiques.