1-(1-((4-chlorophenyl)sulfonyl)-1H-indol-3-yl)ethan-1-one | 104142-23-6

• 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-(1-((4-chlorophenyl)sulfonyl)-1H-indol-3-yl)ethan-1-one
• 英文别名: 1-[1-(4-Chlorophenyl)sulfonylindol-3-yl]ethanone
• CAS: 104142-23-6
• 化学式: C₁₆H₁₂ClNO₃S
• 分子量: 333.795
• InChiKey: KCOUPFLSOSTNNO-UHFFFAOYSA-N

物化性质

• 沸点：
  530.3±56.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(1-((4-chlorophenyl)sulfonyl)-1H-indol-3-yl)ethan-1-one 在 盐酸 、 溶剂黄146 、 二乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 3-(2-(N-(4-chloro-benzenesulfonyl)-1H-indol-3-yl)-2-oxo-ethylidene)indolin-2-one
  参考文献：
  名称：

  Synthesis and Bioactivity Assessment of Novel Spiro Pyrazole-Oxindole Congeners Exhibiting Potent and Selective in vitro Anticancer Effects

  摘要：

  本研究旨在设计和合成新型的螺环吡唑-3,3'-氧化吲哚类似物系列，并研究它们作为抗氧化剂和抗微生物剂的生物活性，以及相对于健康的非癌细胞控制皮肤成纤维细胞（BJ-1）对选定的人类癌细胞系（即乳腺癌MCF-7、结肠癌HCT-116和肝癌HepG-2）的抗增殖效力。通过免疫测定关键的抗凋亡和促凋亡蛋白标记物水平，也对它们的细胞毒活性机制进行了研究。所有合成目标同系物的分析和光谱数据与它们的结构相符。合成的化合物表现出多样的中等至强大的抗微生物和抗氧化活性。MTT实验结果显示，七种合成的化合物（即11a、11b、12a、12b、13b、13c和13h）特别对所研究的三种癌细胞系表现出显著的细胞毒性。获得的IC50值范围分别为5.7-21.3和5.8-37.4µg/mL，相对于健康的非癌化疗药物多柔比星，这分别是3.8和6.5倍（基于最小IC50值）更显著的。在HepG-2细胞中，类似物13h表现出最高的细胞毒性，IC50值为19.2µg/mL，相对于多柔比星（IC50=21.6µg/mL）。观察到的细胞毒性是特异性的，证明在非癌细胞控制皮肤成纤维细胞中毒性极小。ELISA结果表明，针对检测的癌细胞系的观察到的抗增殖效果是通过促进凋亡的激活介导的，如显著增加的促凋亡蛋白标记物（p53、bax和caspase-3）和减少的抗凋亡标记物bcl-2所示。综合以上结果，本研究结果强调了螺环吡唑-氧化吲哚类似物作为针对人类癌细胞的有价值的候选抗癌剂的潜力。

  DOI：

  10.3390/molecules25051124
• 作为产物：
  描述：

  1-(4-氯-苯磺酰基)-2-甲基-1H-吲哚-3-甲醛 在 2-甲氧基乙胺 作用下， 生成 1-(1-((4-chlorophenyl)sulfonyl)-1H-indol-3-yl)ethan-1-one
  参考文献：
  名称：

  N-磺酰基吲哚3-醛和酮的新型重排

  摘要：

  在用伯胺处理时，将3-乙酰基和3-甲酰基-2-甲基-N-磺酰基吲哚部分互变。

  DOI：

  10.1039/c39860000634

文献信息

• Synthesis and Quantitative Structure–Activity Relationship (QSAR) Study of Novel <i>N</i>-Arylsulfonyl-3-acylindole Arylcarbonyl Hydrazone Derivatives as Nematicidal Agents
  作者：Zhiping Che、Shaoyong Zhang、Yonghua Shao、Lingling Fan、Hui Xu、Xiang Yu、Xiaoyan Zhi、Xiaojun Yao、Rui Zhang

  DOI：10.1021/jf400536q

  日期：2013.6.19

  natural-product-based pesticidal agents, 54 novel N-arylsulfonyl-3-acylindole arylcarbonyl hydrazone derivatives were prepared, and their structures were well characterized by 1H NMR, 13C NMR, HRMS, ESI-MS, and mp. Their nematicidal activity was evaluated against that of the pine wood nematode, Bursaphelenchus xylophilus in vivo. Among all of the derivatives, especially V-12 and V-39 displayed the best

  在我们旨在发现和开发基于天然产物的杀虫剂的程序的继续中，制备了54种新颖的N-芳基磺酰基-3-酰基亚芳基芳基羰基hydr衍生物，并通过1 H NMR，13 C NMR对其结构进行了很好的表征， HRMS，ESI-MS和mp。在体内对它们的杀线虫活性针对松木线虫Bursaphelenchus xylophilus进行了评估。在所有衍生物中，尤其是V-12和V-39表现出最有希望的杀线虫活性，LC 50值分别为1.0969和1.2632 mg / L。这建议引入R 1和R 2为了进一步制备这些作为杀线虫剂的化合物，可以考虑将R 3作为吸电子取代基，R 3作为甲基，R 4作为苯基作为具有吸电子取代基的化合物。六个选定的描述符是WHIM描述符（E1m），两个GETAWAY描述符（R1m +和R3m +），负担特征值描述符（BEHm8）和两个边缘邻接索引描述符（EEig05x和EEig13d）。定量
• Access to Biaryl Sulfonamides by Palladium-Catalyzed Intramolecular Oxidative Coupling and Subsequent Nucleophilic Ring Opening of Heterobiaryl Sultams with Amines
  作者：Joydev K. Laha、Neetu Dayal、Krupal P. Jethava、Dilip V. Prajapati

  DOI：10.1021/acs.orglett.5b00290

  日期：2015.3.6

  The installation of sulfonamide pharmacophores on heterobiaryls has successfully been executed by a previously unknown palladium-catalyzed intramolecular oxidative coupling in N-arylsulfonyl heterocycles followed by novel ring opening of heterobiaryl sultams with amine nucleophiles. The protocol has a wide scope of substrates warranting broad applications in the synthesis of heterobiaryls containing

  磺酰胺药效基团在杂二芳基化合物上的安装已成功地通过在N-芳基磺酰基杂环中进行钯催化的分子内氧化偶合反应完成，随后通过胺类亲核试剂实现了杂二芳基磺胺类化合物的新型开环。该方案具有广泛的底物范围，可确保在合成含邻磺酰基或羧基官能团的杂二芳基化合物中具有广泛的应用。
• Anti HIV-1 agents 5: Synthesis and anti-HIV-1 activity of some N-arylsulfonyl-3-acetylindoles in vitro
  作者：Jun-Qiang Ran、Ning Huang、Hui Xu、Liu-Meng Yang、Min Lv、Yong-Tang Zheng

  DOI：10.1016/j.bmcl.2010.04.132

  日期：2010.6

  In continuation of our program aimed at the discovery and development of compounds with superior anti-human immunodeficiency virus type 1 (HIV-1) activity, 21N-arylsulfonyl-3-acetylindole analogs (2a-u) were synthesized and preliminarily evaluated as HIV-1 inhibitors in vitro. Among of all the analogs, several compounds exhibited significant anti-HIV-1 activity, especially N-phenylsulfonyl-3-acetyl-6-methylindole (2j) and N-(p-ethyl)phenylsulfonyl-3-acetyl-6-methylindole (2n) showed the most potent anti-HIV-1 activity with EC50 values of 0.36 and 0.13 mu g/mL, and TI values of >555.55 and 791.85, respectively. It demonstrated that introduction of the acetyl group at the 3-position of N-arylsulfonyl-6-methylindoles could generally lead to the more potent analogs. (C) 2010 Elsevier Ltd. All rights reserved.
• BASS, R. J.;EVANS, T. J., J. CHEM. SOC. CHEM. COMMUN., 1986, N 8, 634-635
  作者：BASS, R. J.、EVANS, T. J.

  DOI：——

  日期：——
• Synthesis and Bioactivity Assessment of Novel Spiro Pyrazole-Oxindole Congeners Exhibiting Potent and Selective in vitro Anticancer Effects
  作者：Heba M. Abo-Salem、Amr Nassrallah、Ahmed A.F. Soliman、Manal S. Ebied、Mohamed E. Elawady、Sayeda A. Abdelhamid、Eslam R. El-Sawy、Yazeed A. Al-Sheikh、Mourad A. M. Aboul-Soud

  DOI：10.3390/molecules25051124

  日期：——

  The present work aims to design and synthesize novel series of spiro pyrazole-3,3’-oxindoles analogues and investigate their bioactivity as antioxidant and antimicrobial agents, as well as antiproliferative potency against selected human cancerous cell lines (i.e., breast, MCF-7; colon, HCT-116 and liver, HepG-2) relative to healthy noncancerous control skin fibroblast cells (BJ-1). The mechanism of their cytotoxic activity has been also examined by immunoassaying the levels of key anti- and proapoptotic protein markers. The analytical and spectral data of the all synthesized target congeners were compatible with their structures. Synthesized compounds showed diverse moderate to powerful antimicrobial and antioxidant activities. Results of MTT assay revealed that seven synthesized compounds (i.e., 11a, 11b, 12a, 12b, 13b, 13c and 13h) particularly exhibited significant cytotoxicity against the three cancerous cell lines under investigation. Ranges of IC50 values obtained were 5.7–21.3 and 5.8–37.4 µg/mL against HCT-116 and MCF-7, respectively; which is 3.8 and 6.5-fold (based on the least IC50 values) more significant relative to the reference chemotherapeutic drug doxorubicin. In HepG-2 cells, the analogue 13h exhibited the highest cytotoxicity with IC50 value of 19.2µg/mL relative to doxorubicin (IC50 = 21.6µg/mL). The observed cytotoxicity was specific to cancerous cells, as evidenced by the minimal toxicity in the noncancerous control skin-fibroblast cells. ELISA results indicated that the observed antiproliferative effect against examined cancer cell lines is mediated via engaging the activation of apoptosis as illustrated by the significant increase in proapoptotic protein markers (p53, bax and caspase-3) and reduction in the antiapoptotic marker bcl-2. Taken together, results of the present study emphasize the potential of spiro pyrazole-oxindole analogues as valuable candidate anticancer agents against human cancer cells.

  本研究旨在设计和合成新型的螺环吡唑-3,3'-氧化吲哚类似物系列，并研究它们作为抗氧化剂和抗微生物剂的生物活性，以及相对于健康的非癌细胞控制皮肤成纤维细胞（BJ-1）对选定的人类癌细胞系（即乳腺癌MCF-7、结肠癌HCT-116和肝癌HepG-2）的抗增殖效力。通过免疫测定关键的抗凋亡和促凋亡蛋白标记物水平，也对它们的细胞毒活性机制进行了研究。所有合成目标同系物的分析和光谱数据与它们的结构相符。合成的化合物表现出多样的中等至强大的抗微生物和抗氧化活性。MTT实验结果显示，七种合成的化合物（即11a、11b、12a、12b、13b、13c和13h）特别对所研究的三种癌细胞系表现出显著的细胞毒性。获得的IC50值范围分别为5.7-21.3和5.8-37.4µg/mL，相对于健康的非癌化疗药物多柔比星，这分别是3.8和6.5倍（基于最小IC50值）更显著的。在HepG-2细胞中，类似物13h表现出最高的细胞毒性，IC50值为19.2µg/mL，相对于多柔比星（IC50=21.6µg/mL）。观察到的细胞毒性是特异性的，证明在非癌细胞控制皮肤成纤维细胞中毒性极小。ELISA结果表明，针对检测的癌细胞系的观察到的抗增殖效果是通过促进凋亡的激活介导的，如显著增加的促凋亡蛋白标记物（p53、bax和caspase-3）和减少的抗凋亡标记物bcl-2所示。综合以上结果，本研究结果强调了螺环吡唑-氧化吲哚类似物作为针对人类癌细胞的有价值的候选抗癌剂的潜力。