1-(phenylsulfonyl)-1H-indole-4-carbaldehyde | 146073-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(phenylsulfonyl)-1H-indole-4-carbaldehyde
• 英文别名: 1-(benzenesulphonyl)-1H-indole-4-carboxaldehyde；1-(phenylsulfonyl)-1H-Indole-4-carboxaldehyde；1-(benzenesulfonyl)indole-4-carbaldehyde
• CAS: 146073-06-5
• 化学式: C₁₅H₁₁NO₃S
• 分子量: 285.323
• InChiKey: RGHYYVXXCUUNLA-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  513.6±42.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(phenylsulfonyl)-1H-indole-4-carbaldehyde 在 盐酸 、 ammonium acetate 、 汞 、 锌 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 2-[1-(benzenesulphonyl)-1H-indol-4-yl]ethylamine
  参考文献：
  名称：

  N-Arylsulfonylindole Derivatives as Serotonin 5-HT₆ Receptor Ligands

  摘要：

  A series of N-1-arylsulfonyltryptamines were found to be potent ligands of the human serotonin 5-HT6 receptor with the 5-methoxy-1-benzenesulfonyl analogue (19) having the highest affinity. Additionally, it was discovered that a group such as 3-(3-methoxybenzyl)-1,2,4-oxadiazol-5-yI in the 2-position of the indole ring (43) can replace the arylsulfonyl substituent in the 1-position with no loss of affinity. This suggested that the binding conformation of the aminoethyl side chain at this receptor was toward the 4-position of the indole ring and was supported by the fact that the 4-(aminoethyl)indoles (45) also displayed high affinity, as did the conformationally rigid 1,3,4,5-tetrahydrobenz[c,d]indole (49). Molecular modeling showed that 19, 43, and 45 all had low-energy conformers that overlaid well onto 49. Both 19 and 49 had good selectivity over other serotonin receptors tested, with 49 also showing excellent selectivity over all dopamine receptors. In a functional adenylate cyclase stimulation assay, 19 and 49 had no agonist activity, whereas 45 behaved as a partial agonist. Finally, it was shown that 19 had good activity in the 5-HT2A centrally mediated mescaline-induced head twitch assay, which implies that it is brain-penetrant.

  DOI：

  10.1021/jm010943m
• 作为产物：
  描述：

  4-吲哚甲醛 在 苯磺酰氯 作用下， 以 N-甲基乙酰胺 、 乙酸乙酯 为溶剂， 生成 1-(phenylsulfonyl)-1H-indole-4-carbaldehyde
  参考文献：
  名称：

  Thiazolidinedione derivatives, method for preparing the derivatives and

  摘要：

  以下是通用公式（I）所代表的噻唑烷二酮衍生物：##STR1## 其中虚线代表单键或双键，噻唑烷二酮环残基连接到吲哚环的2-、3-、4-、5-和6-位置中的任一位置，R代表从氢原子和烷基、烯基、炔基、苯基、芳基烷基、杂环烷基、芳基磺酰基和芳基氨基甲酰基组成的群中选择的一个群！或其药学上可接受的盐表现出降低血糖水平和降低血液中脂质浓度的优异效果，因此可用作治疗糖尿病的治疗剂。这些衍生物及其药学上可接受的盐几乎没有任何副作用。

  公开号：

  US05811439A1

文献信息

• [EN] N-ACYLHYDRAZONE DERIVATIVES FOR SELECTIVE T CELL INHIBITOR AND ANTI-LYMPHOID MALIGNANCY DRUG<br/>[FR] DÉRIVÉS DE N-ACYLHYDRAZONE DESTINÉS À UN MÉDICAMENT ANTIMALIGNITÉ LYMPHOÏDE ET INHIBANT SÉLECTIVEMENT LES LYMPHOCYTES T
  申请人：CHONG KUN DANG PHARM CORP

  公开号：WO2014035149A1

  公开（公告）日：2014-03-06

  The present invention relates to novel N-acylhydrazone derivatives, and more particularly to novel N-acylhydrazone derivatives having selective T cell inhibitory activity and/or anti-lymphoid malignancy activity, stereoisomers thereof, pharmaceutically acceptable salts thereof, the use thereof for preparing pharmaceutical compositions, pharmaceutical compositions containing the same, treatment methods using the compositions, and methods for preparing the novel N-acylhydrazone derivatives.

  本发明涉及新型的N-酰腙衍生物，特别是具有选择性的T细胞抑制活性和对淋巴细胞恶性肿瘤的活性的新型N-酰腙衍生物，其立体异构体，可药用的盐，以及使用它们来制备药物组合物，包含它们的药物组合物，使用该组合物的治疗方法，以及制备新型N-酰腙衍生物的方法。
• Synthesis and evaluation of selenium-containing indole chalcone and diarylketone derivatives as tubulin polymerization inhibition agents
  作者：Shun Zhang、Baijiao An、Jiayan Li、Jinhui Hu、Ling Huang、Xingshu Li、Albert S. C. Chan

  DOI：10.1039/c7ob01655g

  日期：——

  chalcone and diarylketone derivatives were synthesized and evaluated as tubulin polymerization inhibitors. Among them, compound 25b exhibited the most potent antiproliferative activities against six human cancer cell lines with IC50 values of 0.004–0.022 μM. A microtubule dynamics assay and an immunofluorescence assay confirmed that 25b could effectively inhibit tubulin polymerization (IC50 = 2.1 ± 0.27 μM)

  合成了十六种新的含硒的吲哚查尔酮和二芳基酮衍生物，并将其评估为微管蛋白聚合抑制剂。其中，化合物25b对六种人类癌细胞系表现出最有效的抗增殖活性，IC 50值为0.004-0.022μM。微管动力学分析和免疫荧光分析证实25b可有效抑制微管蛋白聚合（IC 50 = 2.1±0.27μM）。进一步的细胞机制研究表明25b诱导了G2 / M期阻滞，线粒体膜电位（MMP）的降低进一步证明了这一点。
• Synthesis and Biological Evaluation of 1-Arylsulfonyl-5-(<i>N</i>-hydroxyacrylamide)indoles as Potent Histone Deacetylase Inhibitors with Antitumor Activity in Vivo
  作者：Mei-Jung Lai、Han-Li Huang、Shiow-Lin Pan、Yi-Min Liu、Chieh-Yu Peng、Hsueh-Yun Lee、Teng-Kuang Yeh、Po-Hsien Huang、Che-Ming Teng、Ching-Shih Chen、Hsun-Yueh Chuang、Jing-Ping Liou

  DOI：10.1021/jm300197a

  日期：2012.4.26

  has been identified as a new class of histone deacetylase inhibitors. Compounds 8, 11, 12, 13, and 14 demonstrated stronger antiproliferative activities than 1 (SAHA) with GI50 values ranging from 0.36 to 1.21 μM against Hep3B, MDA-MB-231, PC-3, and A549 human cancer cell lines. Lead compound 8 showed remarkable HDAC 1, 2, and 6 isoenzymes inhibitory activities with IC50 values of 12.3, 4.0, 1.0 nM

  一系列 1-芳基磺酰基-5-( N-羟基丙烯酰胺) 吲哚已被确定为一类新的组蛋白脱乙酰酶抑制剂。化合物8，11，12，13，和14种显示出更强的抗增殖活性比1（SAHA）与GI 50个值范围从0.36至1.21μM针对的Hep3B，MDA-MB-231，PC-3，和A549人癌细胞系。先导化合物8显示出显着的 HDAC 1、2 和 6 同工酶抑制活性，IC 50值分别为 12.3、4.0、1.0 nM，与1. 在针对肺 A549 异种移植模型的体内功效评估中，8显示出比化合物1更好的抗肿瘤活性。
• A facile preparation of N-protected indolaldehydes using a modified Hass procedure
  作者：Arasambattu K. Mohanakrishnan、Ramalingam Balamurugan、Neelamegam Ramesh

  DOI：10.1016/j.tetlet.2005.09.121

  日期：2005.11

  The preparation of a variety of N-protected indolaldehydes is reported via the reaction of N-protected bromomethylindoles with 2-nitropropane using NaH/DMF.

  通过使用NaH / DMF使N-保护的溴甲基吲哚与2-硝基丙烷反应，报道了各种N-保护的吲哚醛的制备。
• Design, synthesis, and biological evaluation of cyclic-indole derivatives as anti-tumor agents via the inhibition of tubulin polymerization
  作者：Jun Yan、Jinhui Hu、Baijiao An、Li Huang、Xingshu Li

  DOI：10.1016/j.ejmech.2016.09.056

  日期：2017.1

  revealed a new attractive cyclic-indole scaffold for the discovery of mitosis-targeting anti-tumour agents. Among all of the synthesized derivatives, compound 20 displayed the most potent anti-proliferative activity (with IC50 values of 22–56 nM against seven cancer cell lines) and tubulin polymerization inhibition (IC50 = 0.15 ± 0.07 μM), which were much better than those of the reference compound Combretastain

  这项研究揭示了一种新的有吸引力的环状吲哚支架，用于发现靶向有丝分裂的抗肿瘤剂。在所有合成的衍生物中，化合物20显示出最有效的抗增殖活性（针对7种癌细胞系的IC 50值为22–56 nM）和微管蛋白聚合抑制（IC 50  = 0.15±0.07μM），这是非常重要的。优于参考化合物Combretastain A-4（CA-4）。还观察到化合物20对人正常细胞和癌细胞的高选择性（9.68–7.61）。免疫荧光分析阐明了化合物20破坏细胞内微管网络并干扰细胞有丝分裂。细胞机制研究表明，化合物20使细胞周期停滞在G 2 / M期，并以时间和剂量依赖性方式诱导细胞凋亡。总之，化合物20值得进一步研究进行体内抗肿瘤评估。