1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]ethan-1-one | 1149724-09-3

• 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: 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]ethan-1-one
• 英文别名: 1-(Benzotriazol-1-yl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]ethanone
• CAS: 1149724-09-3
• 化学式: C₂₅H₁₉ClN₄O₃
• 分子量: 458.904
• InChiKey: GTFVUOFRWWPWBK-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  614.5±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]ethan-1-one 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 34.0h， 生成 1,3,4,6-tetra-O-acetyl-2-[(N-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetyl)-4-aminobutanoyl)-amino]-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis and characterisation of glucosamine–NSAID bioconjugates

  摘要：

  合成策略以制备非甾体抗炎药物 - 葡萄糖胺生物结合物。

  DOI：

  10.1039/c4ob01681e
• 作为产物：
  描述：

  吲哚美辛 、 苯并三唑-1-碳酰氯 在 三乙胺 作用下， 生成 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]ethan-1-one
  参考文献：
  名称：

  The novel phosphoramidate derivatives of NSAID 3-hydroxypropylamides: Synthesis, cytostatic and antiviral activity evaluations

  摘要：

  The target phosphoramidates 5a-e were prepared in one step from 3-hydroxypropyl derivatives 3a-e of nonsteroidal anti-inflammatory drugs (fenoprofen, ketoprofen, ibuprofen, indomethacin, diclofenac). The products 3a-e and 5a-e were evaluated for their cytostatic and antiviral activity against malignant tumour cell lines and normal human fibroblasts (WI 38). All phosphoramidate derivatives 5a-e possess significantly greater inhibitory activities than the corresponding 3-hydroxypropyl derivatives 3a-e, whereby compound 5a showed the most potent inhibitory activities against cervical, pancreatic and colon carcinoma cell lines (IC50 = 5 - 7 mu M), (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.037

文献信息

• Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
  作者：Erdong Qu、Shangzhang Li、Jin Bai、Yan Zheng、Wanfang Li

  DOI：10.1021/acs.orglett.1c03535

  日期：2022.1.14

  Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to

  在此，我们报道了一种方便获得的N-酰基苯并三唑与烷基、烯基和芳基硝基化合物的 Ni 催化还原转酰胺基反应，该反应以良好的收率和广泛的底物范围提供了各种酰胺。相同的催化反应条件也适用于N-磺酰基苯并三唑，它可以与硝基芳烃和硝基烷烃进行平滑的还原偶联，得到相应的磺酰胺。
• Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkers
  作者：Anand D. Tiwari、Siva S. Panda、Adel S. Girgis、Sandhyamayee Sahu、Riham F. George、Aladdin M. Srour、Brian La Starza、Abdullah M. Asiri、C. Dennis Hall、Alan R. Katritzky

  DOI：10.1039/c4ob01281j

  日期：——

  Novel, non-steroidal anti-inflammatory drug (NSAID), acetaminophen conjugates 6a–l with amino acid linkers were synthesized utilizing benzotriazole chemistry. Biological data acquired for all the novel bis-conjugates showed (a) some bis-conjugates (6d, 6e, 6h, and 6k) exhibit more potent anti-inflammatory activity than their parent drugs, (b) the potent bis-conjugates show no visible stomach lesions

  新型非甾体抗炎药（NSAID），具有氨基酸连接基的对乙酰氨基酚共轭物6a-1，是利用苯并三唑化学方法合成的。获得的所有新型双结合物的生物学数据表明（a）一些双结合物（6d，6e，6h和6k）比其母体药物显示出更强的抗炎活性，（b）强大的双结合物没有显示出与高度致溃疡的母体药物相比，可见的胃部病变明显；（c）有效的生物活性化合物在应用抗炎剂量的5倍时没有死亡率或毒性症状。具有统计学意义的QSAR模型，描述了6a–l的抗炎特性（使用验证所观察到的生物活性的CODESSA-Pro获得N＝ 15，n＝ 3，R 2＝ 0.891，R 2 cvOO ＝ 0.770，R 2 cvMO ＝ 0.796，F＝ 29.904，s 2＝ 0.011）。
• B₂(OH)₄-Mediated Reductive Transamidation of <i>N</i>-Acyl Benzotriazoles with Nitro Compounds En Route to Aqueous Amide Synthesis
  作者：Jin Bai、Shangzhang Li、Riqian Zhu、Yang Li、Wanfang Li

  DOI：10.1021/acs.joc.2c02995

  日期：2023.3.17

  We herein developed a reductive transamidation reaction between N-acyl benzotriazoles (AcBt) and organic nitro compounds or NaNO2 under mild conditions. This protocol employed the stable and readily available B2(OH)4 as the reducing agent and H2O as the ideal solvent. N-Deuterated amides can be synthesized when conducting the reaction in D2O. A reasonable reaction mechanism involving bond metathesis

  我们在此开发了N -酰基苯并三唑 (AcBt) 与有机硝基化合物或 NaNO 2在温和条件下的还原转酰胺基反应。该方案使用稳定且易于获得的 B 2 (OH) 4作为还原剂，使用 H 2 O 作为理想溶剂。当在 D 2 O中进行反应时，可以合成N-氘代酰胺。提出了一个合理的反应机制，包括 AcBt 酰胺和氨基硼酸中间体之间的键复分解，以解释 AcBt 的独特性质。
• NSAID Conjugates with Carnosine and Amino Acids
  作者：Alan Katritzky、Sandhyamayee Sahu、Siva Panda、Abdullah Asiri

  DOI：10.1055/s-0033-1339920

  日期：——

  Benzotriazole-mediated syntheses of novel bioconjugates of nonsteroidal anti-inflammatory drugs with carnosine and with amino acids were prepared in yields of 50-97% as potential drug candidates.