1-(3-(1H-indol-1-yl)propyl)-1H-indole | 95365-94-9

• 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-(3-(1H-indol-1-yl)propyl)-1H-indole
• 英文别名: 1,1'-(propane-1,3-diyl)di(1H-indole)；1,3-bis-(indol-1-yl)propane；1,3-bis(N-indolyl)propane；1,3-di(indol-1-yl)propane；1,1'-propane-1,3-diyl-bis-indole；1,3-Bis-<2-phenyl-indolyl-1>-propan；1,3-Bis-(indol-1-yl)-propane；1-(3-indol-1-ylpropyl)indole
• CAS: 95365-94-9
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: UPXANNOEORKJCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(3-(1H-indol-1-yl)propyl)-1H-indole 在 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.25h， 生成 methyl (2S)-2-[[2-[1-[3-[3-[2-[[(1S)-2-methoxy-1-methyl-2-oxo-ethyl]amino]-2-oxo-acetyl]indol-1-yl]propyl]indol-3-yl]-2-oxo-acetyl]amino]propanoate
  参考文献：
  名称：

  Synthesis of amino acid appended indoles: Appreciable anti-fungal activity and inhibition of ergosterol biosynthesis as their probable mode of action

  摘要：

  Rationally designed compounds consisting of mono- and di-peptide appendages on bis-indole template were synthesized in appreciable yield. Some of these compounds exhibited significant antifungal activities against Candida albicans with their MIC80 in μg/ml range. However, when used in combination with azoles, the antifungal activities of the azoles were considerably enhanced. The growth inhibition appeared to be specific to the fungal cells and mammalian cells were not affected by these compounds. It is shown that these compounds lower ergosterol levels in the fungal cells and probably act by targeting lanosterol 14α-demethylase, a key enzyme in the sterol biosynthetic pathway of C. albicans. The compounds do not appear to directly act on the fungal cell wall. Hence, the sensitivity of the fungal cells to these compounds cannot be attributed to cell wall damage and consequent accumulation of the compounds in the cell, though defects in cell wall due to defective sterol biosynthesis cannot be completely ruled out.

  DOI：

  10.1016/j.ejmech.2014.04.063
• 作为产物：
  描述：

  1,3-bis-(2,3-dihydroindol-1-yl)propane 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 60.0h， 以30%的产率得到1-(3-(1H-indol-1-yl)propyl)-1H-indole
  参考文献：
  名称：

  Fascaplysin启发的二吲哚类化合物作为CDK4 / cyclin D1的选择性抑制剂

  摘要：

  我们目前的设计，合成和一个新的一系列取代的3-（2-（1的生物活性的ħ -吲哚-1-基）乙基）-1 ħ -indoles和1,2-二（1 ħ -吲哚-1-烷基）烷烃作为CDK4 /细胞周期蛋白D1的选择性抑制剂。设计这些化合物以探索吲哚基部分的连接模式与其CDK抑制活性之间的关系。与紧密相关的CDK2 / cyclin A相比，我们发现所有上述设计的化合物都是CDK4 / cyclin D1的选择性抑制剂，最佳化合物10m和13a的IC 50分别为39和37μm。

  DOI：

  10.1016/j.bmc.2009.06.070

文献信息

• Catalytic assay of Schiff base Co(II), Ni(II), Cu(II) and Zn(II) complexes for N-alkylation of heterocycles with 1,3-dibromopropane
  作者：Sujit Hegade、Yuvraj Jadhav、Sanjay Chavan、Ganpatrao Mulik、Gautam Gaikwad

  DOI：10.1007/s12039-020-01791-4

  日期：2020.12

  AbstractN-alkylation of heterocycles with 1,3-dibromopropane using Schiff base Co(II), Ni(II), Cu(II) and Zn(II) transition metal complexes as a catalyst was studied in 1:1 and 2:1 coupling ratios under mild conditions. It was observed that all the complexes worked as efficient catalyst with product yield 78–92% for coupling ratio 1:1 and product yield 63–78% for coupling ratio 2:1. N-alkylation of

  摘要以席夫碱Co（II），Ni（II），Cu（II）和Zn（II）过渡金属配合物为催化剂，用1,3-二溴丙烷进行杂环的N-烷基化研究温和条件下的比率。可以观察到，所有的配合物都是有效的催化剂，偶合比为1：1时产物收率为78-92％，偶合比为2：1时产物收率为63-78％。与1：3-二溴丙烷以1：1的偶联比例进行杂环的N-烷基化相比，与2：1的偶联比例的N-烷基化操作更为容易，产率更高。 图形摘要1,3-二溴丙烷的杂环N-烷基化
• Regioselective synthesis of mono- and bis-decahydrobenzocarbazoles via tandem reactions of α-diazo ketones
  作者：Sengodagounder Muthusamy、Chidambaram Gunanathan、Eringathodi Suresh

  DOI：10.1016/j.tet.2004.06.053

  日期：2004.8

  Regioselective intermolecular 1,3-dipolar cycloaddition reactions of rhodium generated carbonyl ylides with indoles are reported in this paper. Intermolecular 1,3-dipolar cycloaddition reactions of five-membered-ring cyclic carbonyl ylides with indole and substituted indoles afforded hexahydro-2H-carbazol-2-ones in a regioselective manner. Similarly, reactions of cyclic carbonyl ylides were carried

  本文报道了铑生成的羰基化物与吲哚的区域选择性分子间1,3-偶极环加成反应。五元环环状羰基羰基化物与吲哚和取代的吲哚的分子间1,3-偶极环加成反应以区域选择性方式提供了六氢-2 H-咔唑-2-酮。类似地，进行环状羰基酰基化物的反应以提供具有高区域选择性的十氢苯并[ c ]咔唑或十氢环戊[ c ]咔唑。有趣的是，其他可能的区域异构体十氢苯并[ a]通过环羰基羰基化合物和具有吸电子取代基的吲哚反应也可以得到]咔唑。区域异构体6,11c-环氧-1,2,3,4,4a，5,6,6a，11b，11c-十氢-4a-甲基-5-氧代-7 H-苯并[ c ]咔唑的结构和立体化学和11-苯磺酰基-6,11b-环氧-2,3,4,4a，5,6,6a，11,11a，11b-十氢-4a-甲基-5-氧代-1 H-苯并[ a]单晶X射线分析明确证实了]咔唑。为了推进该研究，首次证明了具有不同芳基和烷基间隔基的双吲哚的五元环环
• Rhodium(II) catalyzed intermolecular double C-alkylation: a method for the synthesis of tetraindoles and indolophanes
  作者：Sengodagounder Muthusamy、Thangaraju Karikalan、Chidambaram Gunanathan、Eringathodi Suresh

  DOI：10.1016/j.tet.2011.11.073

  日期：2012.2

  Double C-alkylation of cyclic diazoamides or bis-diazoamides with indoles or bis-indoles has been achieved to synthesize tetraindole derivatives using rhodium(II) acetate as a catalyst under mild reaction conditions with complete regioselectivity. The intermolecular double C-alkylation reaction strategy was successfully applied to synthesize indolophanes in moderate yield with excellent regiocontrol. The structure and stereochemistry of macrocycles were unequivocally confirmed with the help of single-crystal X-ray structure analyses. (C) 2011 Elsevier Ltd. All rights reserved.
• Cycloadditions. 45. Annulation of heterocycles via intramolecular nitrile oxide-heterocycle cycloaddition reaction
  作者：Wim Dehaen、Alfred Hassner

  DOI：10.1021/jo00002a083

  日期：1991.1
• Fascaplysin-inspired diindolyls as selective inhibitors of CDK4/cyclin D1
  作者：Carine Aubry、A. James Wilson、Daniel Emmerson、Emma Murphy、Yu Yam Chan、Michael P. Dickens、Marcos D. García、Paul R. Jenkins、Sachin Mahale、Bhabatosh Chaudhuri

  DOI：10.1016/j.bmc.2009.06.070

  日期：2009.8

  We present the design, synthesis and biological activity of a new series of substituted 3-(2-(1H-indol-1-yl)ethyl)-1H-indoles and 1,2-di(1H-indol-1-yl)alkanes as selective inhibitors of CDK4/cyclin D1. The compounds were designed to explore the relationship between the connection mode of the indolyl moieties and their CDK inhibitory activities. We found all the above-mentioned designed compounds to

  我们目前的设计，合成和一个新的一系列取代的3-（2-（1的生物活性的ħ -吲哚-1-基）乙基）-1 ħ -indoles和1,2-二（1 ħ -吲哚-1-烷基）烷烃作为CDK4 /细胞周期蛋白D1的选择性抑制剂。设计这些化合物以探索吲哚基部分的连接模式与其CDK抑制活性之间的关系。与紧密相关的CDK2 / cyclin A相比，我们发现所有上述设计的化合物都是CDK4 / cyclin D1的选择性抑制剂，最佳化合物10m和13a的IC 50分别为39和37μm。