4-formylphenyl 4-chlorobenzenesulfonate | 432010-14-5

• 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: 4-formylphenyl 4-chlorobenzenesulfonate
• 英文别名: (4-formylphenyl) 4-chlorobenzenesulfonate
• CAS: 432010-14-5
• 化学式: C₁₃H₉ClO₄S
• mdl: MFCD03081022
• 分子量: 296.731
• InChiKey: VENRVYSFPXVORW-UHFFFAOYSA-N

物化性质

• 沸点：
  466.5±45.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 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：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-formylphenyl 4-chlorobenzenesulfonate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 [4-(Hydroxymethyl)phenyl] 4-chlorobenzenesulfonate
  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 、 4-氯苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以95%的产率得到4-formylphenyl 4-chlorobenzenesulfonate
  参考文献：
  名称：

  作为潜在醛糖还原酶抑制剂的含有喹唑啉-4(3H)-一衍生物的新型磺酸盐库的合成、生物学评价和计算机研究

  摘要：

  一系列含有喹唑啉-4(3 H )-酮环衍生物的新型磺酸盐被设计用于抑制醛糖还原酶（ALR2，EC 1.1.1.21）。磺化醛与 3-氨基-2-烷基喹唑啉-4(3 H )-酮在冰醋酸中反应合成了新型喹唑啉酮衍生物 ( 1–21 )，收率良好 (85%–94%)。使用IR、 1H -NMR、13C -NMR和HRMS对新型分子的结构进行了表征。所有新型喹唑啉酮 ( 1-21 ) 均表现出纳摩尔水平的 ALR2 抑制活性（K I范围为 101.50-2066.00 nM）。此外，与标准抑制剂依帕司他相比，4-[(2-异丙基-4-氧代喹唑啉-3[4 H ]-基亚氨基)甲基]苯基苯磺酸盐( 15 )表现出更高的抑制剂活性，对ALR2的抑制高达7.7倍。使用薛定谔小分子药物发现套件 2021-1 研究了 ALR2 和喹唑啉酮之间的结合相互作用，报告了可能的抑制剂与 ALR2 相互作用。体外和计算机研究结果表明，这些

  DOI：

  10.1002/ddr.21887

文献信息

• Exploring sulfonate esters of 5-arylidene thiazolidine-2,4-diones as PTP1B inhibitors with anti-hyperglycemic activity
  作者：Manoj Kumar Mahapatra、Rajnish Kumar、Manoj Kumar

  DOI：10.1007/s00044-017-2074-8

  日期：2018.2

  sulfonyloxy-5-arylidene thiazolidine-2,4-dione derivatives were synthesized and screened in vitro for PTP1B inhibitory activity and in vivo for anti-hyperglycemic activity. The introduction of aryl/alkyl sulfonate ester moiety was anticipated to yield PTP1B inhibitors with significant potency. Docking results revealed their bidentate nature of binding, and further helped in understanding the binding mode of ligands

  蛋白酪氨酸磷酸酶1B（PTP1B）已被确定为胰岛素和瘦素信号通路的负调节剂，因此被认为是治疗2型糖尿病的新治疗靶标。合成了一系列的十一个芳基/烷基磺酰氧基-5-亚芳基噻唑烷-2,4-二酮衍生物，并在体外筛选了PTP1B抑制活性，并在体内筛选了抗高血糖活性。预期引入芳基/烷基磺酸酯部分将产生具有显着效力的PTP1B抑制剂。对接结果揭示了它们的结合的双齿性质，并进一步帮助了理解PTP1B酶内部配体的结合方式。发现化合物13和14是有效的PTP1B抑制剂，IC 50分别为8.53和6.89 µM。化合物13，14，和18相比，吡格列酮也显示显著降低血糖水平的。
• Design, synthesis, biological evaluations and in silico studies of sulfonate ester derivatives of 2-(2-benzylidenehydrazono)thiazolidin-4-one as potential α-glucosidase inhibitors
  作者：Ramandeep Kaur、Rajnish Kumar、Nilambra Dogra、Ashok Kumar Yadav

  DOI：10.1016/j.molstruc.2021.131266

  日期：2022.1

  A novel series of hydrazolyl linked sulfonate ester analogues of 4-thiazolidinone nucleus has been rationally designed, synthesized and characterized by various spectroscopic techniques including 1H NMR, 13C NMR and mass spectrometry. All of the synthesized derivatives were tested for in vitro α-glucosidase inhibitory activities and antioxidant potential. The investigated compounds displayed appreciable

  合理设计、合成了一系列新型的4-噻唑烷酮核的肼基连接磺酸酯类似物，并通过1 H NMR、13 C NMR和质谱等多种光谱技术对其进行了表征。测试了所有合成衍生物的体外α-葡萄糖苷酶抑制活性和抗氧化潜力。与阿卡波糖 (478.07 ± 1.53 μM) 相比，所研究的化合物显示出明显的α-葡萄糖苷酶抑制作用，IC 50值范围为 42.80 ± 0.48 至 599.04 ± 1.26 μM，并建立了构效关系。此外，最有效的衍生物（7d) 在正常 HEK 细胞中通过 MTT 测定进行评估。体内双糖负荷试验证实（7d）比阿卡波糖（剂量为 20 mg/kg 体重）在降低蔗糖给药后餐后高血糖方面具有更高的功效。计算机程序，即同源建模、分子对接、分子动力学模拟、结合自由能计算和 ADME 预测研究进一步证明了体外和体内生物学研究的结果。
• Synthesis, biological evaluation, and in silico study of novel library sulfonates containing quinazolin‐4(<scp>3<i>H</i></scp>)‐one derivatives as potential aldose reductase inhibitors
  作者：Feyzi Sinan Tokalı、Yeliz Demir、İbrahim Hakkı Demircioğlu、Cüneyt Türkeş、Erbay Kalay、Kıvılcım Şendil、Şükrü Beydemir

  DOI：10.1002/ddr.21887

  日期：——

  A series of novel sulfonates containing quinazolin-4(3H)-one ring derivatives was designed to inhibit aldose reductase (ALR2, EC 1.1.1.21). Novel quinazolinone derivatives (1–21) were synthesized from the reaction of sulfonated aldehydes with 3-amino-2-alkylquinazolin-4(3H)-ones in glacial acetic acid with good yields (85%–94%). The structures of the novel molecules were characterized using IR, 1H-NMR

  一系列含有喹唑啉-4(3 H )-酮环衍生物的新型磺酸盐被设计用于抑制醛糖还原酶（ALR2，EC 1.1.1.21）。磺化醛与 3-氨基-2-烷基喹唑啉-4(3 H )-酮在冰醋酸中反应合成了新型喹唑啉酮衍生物 ( 1–21 )，收率良好 (85%–94%)。使用IR、 1H -NMR、13C -NMR和HRMS对新型分子的结构进行了表征。所有新型喹唑啉酮 ( 1-21 ) 均表现出纳摩尔水平的 ALR2 抑制活性（K I范围为 101.50-2066.00 nM）。此外，与标准抑制剂依帕司他相比，4-[(2-异丙基-4-氧代喹唑啉-3[4 H ]-基亚氨基)甲基]苯基苯磺酸盐( 15 )表现出更高的抑制剂活性，对ALR2的抑制高达7.7倍。使用薛定谔小分子药物发现套件 2021-1 研究了 ALR2 和喹唑啉酮之间的结合相互作用，报告了可能的抑制剂与 ALR2 相互作用。体外和计算机研究结果表明，这些
• A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates
  作者：Hina Andleeb、Imtiaz Khan、Antonio Bauzá、Muhammad Nawaz Tahir、Jim Simpson、Shahid Hameed、Antonio Frontera

  DOI：10.1107/s2053229618008355

  日期：2018.7.1

  To explore the operational role of noncovalent interactions in supramolecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formylphenyl 4-substituted benzenesulfonates was investigated. The compounds are 2-formylphenyl 4-methylbenzenesulfonate, C₁₄H₁₂O₄S, 3a, 2-formylphenyl 4-chlorobenzenesulfonate, C₁₃H₉ClO₄S, 3b, 2-formylphenyl 4-bromobenzenesulfonate, C₁₃H₉BrO₄S, 3c, 4-formylphenyl 4-methylbenzenesulfonate, C₁₄H₁₂O₄S, 4a, 4-formylphenyl 4-chlorobenzenesulfonate, 4b, C₁₃H₉ClO₄S, and 4-formylphenyl 4-bromobenzenesulfonate, C₁₃H₉BrO₄S, 4c. The title compounds were synthesized under basic conditions from salicylaldehyde/4-hydroxybenzaldehydes and various aryl sulfonyl chlorides. Remarkably, halogen-bonding interactions are found to be important to rationalize the solid-state crystal structures. In particular, the formation of O...X (X = Cl and Br) and type I X...X halogen-bonding interactions have been analyzed by means of density functional theory (DFT) calculations and characterized using Bader's theory of `atoms in molecules' and molecular electrostatic potential (MEP) surfaces, confirming the relevance and stabilizing nature of these interactions. They have been compared to antiparallel π-stacking interactions that are formed between the arylsulfonates.

  为了探索非共价相互作用在具有设计拓扑结构的超分子结构中的作用，我们研究了一系列 2-和 4-甲酰基苯基 4-取代苯磺酸盐的固态结构。这些化合物是 2-甲酰基苯基 4-甲基苯磺酸盐 C14H12O4S、3a、2-甲酰基苯基 4-氯苯磺酸盐 C13H9ClO4S、3b、2-甲酰基苯基 4-溴苯磺酸盐 C13H9BrO4S、3c、4-甲基苯磺酸 4-甲酰基苯酯（C14H12O4S）、4a、4-氯苯磺酸 4-甲酰基苯酯（C13H9ClO4S）、4b 和 4-溴苯磺酸 4-甲酰基苯酯（C13H9BrO4S）、4c。标题化合物是在碱性条件下由水杨醛/4-羟基苯甲醛和各种芳基磺酰氯合成的。值得注意的是，卤素键相互作用对固态晶体结构的合理性非常重要。特别是通过密度泛函理论（DFT）计算分析了 O...X（X = Cl 和 Br）和 I 型 X...X卤键相互作用的形成，并利用贝德尔的 "分子中原子 "理论和分子静电势（MEP）表面进行了表征，证实了这些相互作用的相关性和稳定性质。我们将这些相互作用与芳基磺酸盐之间形成的反平行π堆积相互作用进行了比较。
• Regiodivergent C−H Annulation of Imines with Unsymmetrical Alkynes Using Transient Directing Alcohols via Rh(III) Catalysis
  作者：Bairong Liu、Yabo Chen、Qixin Liang、Yuyao Liang、Bifu Liu、Yuan Liu、Yang Gao、Qian Chen、Yanping Huo、Xianwei Li

  DOI：10.1002/adsc.202300167

  日期：2023.6.20

  Regiodivergent [3+2] and [4+2] C−H annulation of imines and imidate esters with unsymmetrical alkynes has been achieved under Rh(III) catalysis. Further transformation of the aldehyde and TMS functionality on the indene products is also demonstrated. The current work highlights the alcohols-directed multiple C−H annulation of imines and imidate esters, leading to diverse fused heterocycles.

  在 Rh(III) 催化下，亚胺和亚氨酸酯与不对称炔烃发生区域发散的 [3+2] 和 [4+2] C−H 环化。还展示了茚产品上醛和 TMS 官能团的进一步转化。目前的工作强调了醇引导的亚胺和亚氨酸酯的多个 C−H 环化，从而产生多种稠合杂环。