4-(2-phenyl-1H-indol-3-yl)benzoic acid methyl ester | 93503-74-3

• 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: 4-(2-phenyl-1H-indol-3-yl)benzoic acid methyl ester
• 英文别名: 2-phenyl-3-(p-methoxycarbonylphenyl)-1H-indole；methyl 4-(2-phenyl-1H-indol-3-yl)benzoate
• CAS: 93503-74-3
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: SKYPGDVIZSGMJH-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  510.5±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-phenyl-1H-indol-3-yl)benzoic acid methyl ester 在 偶氮二甲酸二异丙酯 、 palladium on activated charcoal 、 氢气 、 三苯基膦 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  A synthetic 2,3-diarylindole induces microtubule destabilization and G2/M cell cycle arrest in lung cancer cells

  摘要：

  The anticancer potential of a synthetic 2,3-diarylindole (PCNT13) has been demonstrated in A549 lung cancer cells by inducing both apoptosis and autophagic cell death. In this report, we designed to connect a fluorophore to the compound via a hydrophilic linker for monitoring intracellular localization. The best position for linker attachment was identified from cytotoxicity and effect on cell morphology of newly synthesized PCNT13 derivatives bearing hydrophilic linker. Cytotoxicity and effect on cell morphology related to the parental compound were used to identify the optimum position for linker attachment in the PCNT13 chemical structure. The fluorophore-PCNT13 conjugate was found to localize in the cytoplasm. Microtubules were found to be one of the cytosolic target proteins of PCNT13, as the compound could inhibit tubulin polymerization in vitro. A molecular docking study revealed that PCNT13 binds at the colchicine binding site on the alpha/beta-tubulin heterodimer. The effect of PCNT13 on microtubule dynamics caused cell cycle arrest in the G2/M phase as analyzed by flow cytometric analysis.

  DOI：

  10.1016/j.bmcl.2019.126777
• 作为产物：
  描述：

  4-羰基环己羧酸 在 甲烷磺酸 、 磷酸 、 乙酸酐 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 112.0h， 生成 4-(2-phenyl-1H-indol-3-yl)benzoic acid methyl ester
  参考文献：
  名称：

  Syntheses and complement inhibitory activities of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids

  摘要：

  The syntheses of 4-(2-phenyl-1H-indol-3-yl)cyclohexane-1-carboxylic acids are described. These compounds express potent in vitro inhibition of the human classical complement pathway, and qualitative SAR have been determined. Several of the in vitro active compounds also suppressed the complement dependent reverse passive Arthus reaction (RPAR) in guinea pigs.

  DOI：

  10.1021/jm00380a002

文献信息

• 2,3-Disubstituted Indoles through the Palladium-Catalyzed Reaction of Aryl Chlorides witho-Alkynyltrifluoroacetanilides
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani

  DOI：10.1002/adsc.200606060

  日期：2006.7

  2,3-Disubstituted indoles can be prepared in moderate to excellent yields by reacting readily available o-alkynyltrifluoroacetanilides with aryl chlorides in MeCN at 120 °C in the presence of Pd2(dba)3 and Xphos.

  在Pd 2（dba）3和Xphos的存在下，使易获得的邻炔基三氟乙酰苯胺与芳基氯在MeCN中在120°C下反应，可以以中等至优异的产率制备2,3-二取代的吲哚。
• 2-Substituted 3-arylindoles through palladium-catalyzed arylative cyclization of 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions
  作者：Antonio Arcadi、Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Antonia Iazzetti、Fabio Marinelli

  DOI：10.1039/c2ob27125g

  日期：——

  Free NH 2-substituted 3-arylindoles have been prepared usually in good to high yields through the palladium-catalyzed reaction of readily available 2-alkynyltrifluoroacetanilides with arylboronic acids under oxidative conditions. The reaction tolerates a variety of useful functional groups both in the arylboronic acid and in the alkyne, including chloro, formyl, and ester groups.

  通常通过在氧化条件下，易于获得的2-炔丙基三氟乙酰胺与芳基硼酸在钯催化下的反应，以良好至高产率制备了自由的NH 2-取代的3-芳基吲哚。该反应能够容忍芳基硼酸和炔烃中的多种有用官能团，包括氯、醛和酯基团。
• Dissecting the Electronic Contribution to the Regioselectivity of the Larock Heteroannulation Reaction in the Oxidative Addition and Carbopalladation Steps
  作者：Kanyapat Yiamsawat、Kevin P. Gable、Pitak Chuawong

  DOI：10.1021/acs.joc.1c02560

  日期：2022.1.21

  the regiochemical outcome of the reaction. Density functional theory calculations of the oxidative addition and carbopalladation steps revealed the electronic influences of the substituted 2-iodoaniline derivatives toward the overall rate of the reaction. In contrast, the electronic properties of the asymmetric diarylacetylene remained the critical product-determining factor of regioselectivity.

  制备了取代的 2-碘苯胺衍生物并将其用作反应物，与不对称二芳基乙炔一起，通过 Larock 杂环化反应合成一系列 6-取代的 2,3-二芳基吲哚衍生物。2-碘苯胺衍生物上的给电子取代基阻碍了反应，而吸电子取代基则完全转化为吲哚产物。此外，取代的2-碘苯胺反应物的电子性质对区域选择性没有影响。相反，不对称二芳基乙炔的电子效应显着影响反应的区域化学结果。氧化加成和碳钯化步骤的密度泛函理论计算揭示了取代的 2-碘苯胺衍生物对反应总速率的电子影响。相比之下，不对称二芳基乙炔的电子特性仍然是区域选择性的关键产物决定因素。
• One-Pot and Regiospecific Synthesis of 2,3-Disubstituted Indoles from 2-Bromoanilides via Consecutive Palladium-Catalyzed Sonogashira Coupling, Amidopalladation, and Reductive Elimination
  作者：Bruce Z. Lu、Han-Xun Wei、Yongda Zhang、Wenyi Zhao、Marine Dufour、Guisheng Li、Vittorio Farina、Chris H. Senanayake

  DOI：10.1021/jo302679f

  日期：2013.5.3

  A practical one-pot and regiospecific three-component process for the synthesis of 2,3-disubstituted indoles from 2-bromoanilides was developed via consecutive palladium-catalyzed Sonogashira coupling, amidopalladation, and reductive elimination.

  通过连续的钯催化的Sonogashira偶联，酰胺基钯化和还原消除，开发了一种从2-溴苯胺合成2,3-二取代的吲哚的实用的一锅法和区域特异性三组分方法。
• Regioselectivity of Larock Heteroannulation: A Contribution from Electronic Properties of Diarylacetylenes
  作者：Nared Phetrak、Thanya Rukkijakan、Jakkapan Sirijaraensre、Samran Prabpai、Palangpon Kongsaeree、Chayada Klinchan、Pitak Chuawong

  DOI：10.1021/jo402304s

  日期：2013.12.20

  A series of 2,3-diarylindoles were synthesized from 2-iodoaniline and unsymmetrical diarylacetylenes using the Larock heteroannulation. Diarylacetylenes bearing electron-withdrawing substituents lead to 2,3-diarylindoles with substituted phenyl moieties at the 2-position as major products, while those with electron-donating groups preferably yield indole products with substituted phenyl moieties at the 3-position. The regioisomeric product ratios exhibit a clear correlation with Hammett sigma(p) values. DFT calculations reveal the origin of this effect, displaying smaller activation energy barriers for those pathways leading to the major regioisomer.