2-formylphenyl 4-chlorobenzenesulfonate | 634593-06-9

• 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: 2-formylphenyl 4-chlorobenzenesulfonate
• 英文别名: (2-formylphenyl) 4-chlorobenzenesulfonate
• CAS: 634593-06-9
• 化学式: C₁₃H₉ClO₄S
• mdl: MFCD03217399
• 分子量: 296.731
• InChiKey: SSJRPLPUSNJOFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  464.0±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)：
  3.1
• 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：

  2-formylphenyl 4-chlorobenzenesulfonate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 [2-(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：

  水杨醛 、 4-氯苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到2-formylphenyl 4-chlorobenzenesulfonate
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1107/s2053229618008355

文献信息

• 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。
• Design, synthesis, antioxidant and anticholinesterase activities of novel isonicotinic hydrazide-hydrazone derivatives
  作者：Özlem Aslanhan、Erbay Kalay、Feyzi Sinan Tokalı、Zehra Can、Engin Şahin

  DOI：10.1016/j.molstruc.2023.135037

  日期：2023.5

  techniques. All compounds have shown inhibitory effects against the AChE enzyme at rates ranging from 21.00 to 59.48%. Among them, compound 5 has exhibited the best inhibitory effect of 59.48% against AChE at a concentration of 0.1 mM. Furthermore, to determine how effective the novel compounds are as antioxidants, FRAP and DPPH studies were also carried out. FRAP values in compounds 1-12 were found

  由于该支架具有显着的生物活性，因此腙衍生物的设计和合成日益受到欢迎。在本研究中，通过异烟酰肼与具有磺酸盐部分的苯甲醛的缩合反应合成了 12 种新型异烟酰肼-腙类似物。新化合物的结构已使用光谱技术进行了详细表征。所有化合物都显示出对 AChE 酶的抑制作用，抑制率范围为 21.00 至 59.48%。其中，化合物5在 0.1 mM 浓度下对 AChE 表现出 59.48% 的最佳抑制作用。此外，为了确定新化合物作为抗氧化剂的有效性，还进行了 FRAP 和 DPPH 研究。发现化合物1-12中的FRAP 值范围为 26.989-3415.556 μmol FeSO 4 .7H 2 O/mg。与对照 Trolox （SC 50=0.004) 在 DPPH 自由基清除活动中。可以看出，在 0.1 mM 浓度下，化合物的 AChE 抑制百分比在 23.04-58.10% 的范围内。这是对这些化合物的合成、抗氧化和酶抑制特性的首次研究。
• Synthesis, antioxidant, and anticholinesterase activities of novel <scp><i>N</i>‐arylsulfonyl</scp> hydrazones bearing sulfonate ester scaffold
  作者：Eyüp Başaran

  DOI：10.1002/jccs.202300151

  日期：2023.7

  highest activity in comparison to rivastigmine (501 ± 3.08 μM). This compound (71.42 ± 0.19 μM) is also one of the compounds with the highest activity against BChE. In the BChE assay, 2-hydroxybenzaldehyde-based compound 19 (70.11 ± 0.67 μM) indicated the highest activity in comparison to rivastigmine (19.95 ± 0.20 μM). In antioxidant activity studies, the tested molecules showed lower activities than

  在这项研究中，合成了两个新系列的具有磺酸盐部分的N-芳基磺酰腙化合物( 14 – 25 )，并通过元素分析和各种光谱技术（包括傅里叶变换红外（FT-IR）、 1 H- 和13 C）进行表征。核磁共振（NMR）。这些作为目标分子合成的化合物 ( 14 – 25 ) 进行了体外乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BChE) 抑制活性和抗氧化潜力的测试。测试分子的抗氧化能力通过四种不同的测定法测定。IC 50筛选分子的值针对AChE确定在60.14±0.25–84.81±1.09μM范围内，针对BChE在70.11±0.67–93.60±0.47μM范围内。在 AChE 测定中，与卡巴拉汀 (501 ± 3.08 μM) 相比，基于 4-羟基苯甲醛的化合物25 (60.14 ± 0.25 μM) 显示出最高的活性。该化合物 (71.42 ± 0.19 μM) 也是对抗 BChE 活性最高的化合物之一。在
• Synthesis and Antiproliferative Evaluation of 2′-Arenesulfonyloxy-5-benzylidene-thiazolidine-2,4-diones
  作者：Emily M. Chen、Pei-Jung Lu、Arthur Y. Shaw

  DOI：10.1002/jhet.859

  日期：2012.7

  A series of 2′‐arenesulfonyloxy‐5‐benzylidene‐thiazolidine‐2,4‐diones (TZDs) were synthesized and examined for their antiproliferative effects on a panel of carcinoma cell lines. Our results indicated that initial synthesis of 5‐[2′‐hydroxybenzylidene]‐2,4‐thiazolidinone (9) by Knoevenagel condensation followed by nucleophilic substitution with arylsulfonyl chlorides exhibited superior efficiency to the alternative synthetic route. Among tested compounds, only 8c and 8e showed significant antiproliferative activity against PC‐3 and BT474 cells with GI50 values of 8.4 and 20.6 μM, respectively. SKHep cells displayed interesting structure‐activity relationships in response to TZD derivatives treatment. Alkyl group‐substituted TZD analogs such as 8a (4‐Me, GI50, 9.4 μM) and 8k (4‐iso‐propyl, GI50, 9.8 μM) revealed better antiproliferative activity than those with bulkier alkyl groups. On the other hand, halogen‐substituted TZD analogs 8c, 8h, and 8i showed better antiproliferative activity against H460 cell line. Together, the new synthesized TZD derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p exhibited appreciable antiproliferative activity worth for further study.
• Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells
  作者：Qing Li、Ran An、Yaochun Xu、Mi Zhou、Yan Li、Chun Guo、Renxiao Wang

  DOI：10.1016/j.bmcl.2020.127114

  日期：2020.5

  A lead compound with the (1,3,4-thiadiazol-2-yl) acrylamide scaffold was discovered to have significant cytotoxicity on several tumor cell lines in an in-house cell-based screening. A total of 60 derivative compounds were then synthesized and tested in a CCK-8 cell viability assay. Some of them exhibited improved cytotoxic activities. The most potent compounds had IC50, values of 1-5 mu M on two acute leukemia tumor cell lines, i.e. RS4;11 and HL-60. Flow cytometry analysis of several active compounds and detection of caspase activation indicated that they induced caspase-dependent apoptosis. It was also encouraging to observe that these compounds did not have obvious cytotoxicity on normal cells, i.e. IC50 > 50 mu M on HEK-293T cells. Although the molecular targets of this class of compound are yet to be revealed, our current results suggest that this class of compound represents a new possibility for developing drug candidates against acute leukemia.