4-Formylphenyl 3-nitrobenzenesulfonate | 1334304-62-9

• 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: 4-Formylphenyl 3-nitrobenzenesulfonate
• 英文别名: (4-formylphenyl) 3-nitrobenzenesulfonate
• CAS: 1334304-62-9
• 化学式: C₁₃H₉NO₆S
• 分子量: 307.284
• InChiKey: CQHVYKWIIJFDTG-UHFFFAOYSA-N

物化性质

• 沸点：
  515.9±50.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Formylphenyl 3-nitrobenzenesulfonate 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 [4-[[(5R,5aS,8aR,9R)-5a-chloro-6-oxo-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]oxymethyl]phenyl] 3-nitrobenzenesulfonate
  参考文献：
  名称：

  Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo

  摘要：

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.075
• 作为产物：
  描述：

  对羟基苯甲醛 、 3-硝基苯磺酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-Formylphenyl 3-nitrobenzenesulfonate
  参考文献：
  名称：

  通过腙功能连接到磺酸酯的异烟肼：抗结核活性的设计、合成和评价

  摘要：

  异烟肼 (INH) 是用于治疗全球最致命传染病结核病 (TB) 的关键分子之一。然而，由于出现了耐 INH 的结核分枝杆菌( Mtb ) 菌株，这种基石药物的功效已严重下降。在本研究中，我们旨在化学定制 INH 以克服这种抗性。我们通过腙桥 ( SIH1-SIH13 ) 将 INH 与内部合成的磺酸酯连接，获得了 13 种新化合物。通过 FTIR、1 H NMR、13 C NMR 和 HRMS 进行结构表征后，筛选所有化合物的抗结核病活性携带katG和inhA突变的 H37Rv 菌株和 INH 抗性临床分离株。此外，在三种不同的健康宿主细胞系中评估了SIH1-SIH13的细胞毒性作用；HEK293、IMR-90 和 BEAS-2B。根据获得的数据，合成的化合物似乎是具有低细胞毒性的有吸引力的抗分枝杆菌候选药物。此外，通过在水性介质和 DMSO 中使用 UV/Vis 光谱证实了腙部分在最终化

  DOI：

  10.3390/ph15101301

文献信息

• Isoniazid Linked to Sulfonate Esters via Hydrazone Functionality: Design, Synthesis, and Evaluation of Antitubercular Activity
  作者：Ebru Koçak Aslan、Muhammed İhsan Han、Vagolu Siva Krishna、Rasoul Tamhaev、Cagatay Dengiz、Şengül Dilem Doğan、Christian Lherbet、Lionel Mourey、Tone Tønjum、Miyase Gözde Gündüz

  DOI：10.3390/ph15101301

  日期：——

  overcome this resistance. We obtained thirteen novel compounds by linking INH to in-house synthesized sulfonate esters via a hydrazone bridge (SIH1–SIH13). Following structural characterization by FTIR, 1H NMR, 13C NMR, and HRMS, all compounds were screened for their antitubercular activity against Mtb H37Rv strain and INH-resistant clinical isolates carrying katG and inhA mutations. Additionally, the cytotoxic

  异烟肼 (INH) 是用于治疗全球最致命传染病结核病 (TB) 的关键分子之一。然而，由于出现了耐 INH 的结核分枝杆菌( Mtb ) 菌株，这种基石药物的功效已严重下降。在本研究中，我们旨在化学定制 INH 以克服这种抗性。我们通过腙桥 ( SIH1-SIH13 ) 将 INH 与内部合成的磺酸酯连接，获得了 13 种新化合物。通过 FTIR、1 H NMR、13 C NMR 和 HRMS 进行结构表征后，筛选所有化合物的抗结核病活性携带katG和inhA突变的 H37Rv 菌株和 INH 抗性临床分离株。此外，在三种不同的健康宿主细胞系中评估了SIH1-SIH13的细胞毒性作用；HEK293、IMR-90 和 BEAS-2B。根据获得的数据，合成的化合物似乎是具有低细胞毒性的有吸引力的抗分枝杆菌候选药物。此外，通过在水性介质和 DMSO 中使用 UV/Vis 光谱证实了腙部分在最终化
• Sulfonamides linked to sulfonate esters <i>via</i> hydrazone functionality: synthesis, human carbonic anhydrase inhibitory activities, and molecular modeling studies
  作者：M. İhsan Han、Miyase Gözde Gündüz、Gökçe Alçı、Simone Giovannuzzi、Dönay Yuvalı、Claudiu T. Supuran、Şengül Dilem Doğan

  DOI：10.1039/d2nj05703d

  日期：——

  In the present study, we synthesized novel carbonic anhydrase (CA, EC 4.2.1.1) inhibitors by linking various sulfonate esters to a benzenesulfonamide fragment via hydrazone functionality (SH1–SH14). Following structural characterization using spectral techniques, the obtained molecules were screened for their inhibitory potential against tumor-associated human (h) isoforms hCA IX and XII, along with

  在本研究中，我们通过腙功能 ( SH1–SH14 ) 将各种磺酸酯连接到苯磺酰胺片段，合成了新型碳酸酐酶 (CA, EC 4.2.1.1) 抑制剂。在使用光谱技术进行结构表征后，筛选获得的分子对肿瘤相关人类 (h) 亚型 hCA IX 和 XII 以及生理学上占优势的亚型 hCA I 和 II 的抑制潜力。将甲基、甲氧基或氯取代基引入末端苯环的对位导致最有效的 hCA IX 和/或 hCA XII 抑制剂，其中K i值 < 10 nM。使用计算机技术预测所选化合物的药物相似性和药代动力学特征。最后，最有效的抑制剂 4-((2-(4-氨磺酰基苯甲酰基)亚肼基)甲基)苯基 4-甲氧基苯磺酸盐 ( SH3 ) 对肿瘤相关 hCA 亚型 IX ( K i = 9.4 nM) 和进行XII ( Ki = 5.9 nM ) 以使抑制数据合理化。
• Natural products-based insecticidal agents 11. Synthesis and insecticidal activity of novel 4α-arylsulfonyloxybenzyloxy-2β-chloropodophyllotoxin derivatives against Mythimna separata Walker in vivo
  作者：Hui Xu、Jun-Liang Zhang

  DOI：10.1016/j.bmcl.2011.07.075

  日期：2011.9

  In continuation of our program aimed at the discovery and development of natural products-based insecticidal agents, 14 novel 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxin derivatives were stereoselectively semisynthesized from podophyllotoxin, and preliminarily evaluated for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo. Especially compounds 9c' and 9g' exhibited the most promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach at 1 mg/mL. Generally, it was preliminarily demonstrated that arylsulfonyloxy groups at the C-2 position of benzyloxy moiety and the length of the side chain on the benzenesulfonyloxy group of 4 alpha-arylsulfonyloxybenzyloxy-2 beta-chloropodophyllotoxins might be important for the insecticidal activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of new 4-aminobenzoic acid (PABA) hydrazide-hydrazone/sulfonate hybrids and antimicrobial evaluation with ascorbic acid/salicylic acid/ <i>N</i> -acetyl cysteine combinations
  作者：M. İhsan Han、Ufuk İnce、G. Pelin Coşkun、Kaan Birgül、Şengül Dilem Doğan、Amir Ashoorzadeh、Ş. Güniz Küçükgüzel

  DOI：10.1080/10426507.2024.2341145

  日期：——

  One of the most serious threats to human health is the increasing prevalence of drug-resistant pathogens. The development of new antibiotics capable of combating drug resistance is critical. In var...

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