2-(undecylsulfonyl)acetic acid | 76690-01-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 2-(undecylsulfonyl)acetic acid
• 英文别名: (undecane-1-sulfonyl)-acetic acid；(Undecan-1-sulfonyl)-essigsaeure；2-Undecylsulfonylacetic acid
• CAS: 76690-01-2
• 化学式: C₁₃H₂₆O₄S
• 分子量: 278.413
• InChiKey: IRXGVINFXKCUGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(undecylsulfonyl)acetic acid 、 3,4-二羟基苯甲醛 在 四氢吡咯 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到(E)-4-(2-(undecylsulfonyl)vinyl)benzene-1,2-diol
  参考文献：
  名称：

  Structure-activity relationship studies of (E)-3,4-dihydroxystyryl alkyl sulfones as novel neuroprotective agents based on improved antioxidant, anti-inflammatory activities and BBB permeability

  摘要：

  （E）-3,4-双羟基苯基甲基硫醚作为神经退行性疾病药的新类同代物被设计并合成。生物测试结果表明，在清除自由基以及抗炎性反应中，大多数目标化合物保持了抗氧化和抗炎活性，从而保护神经细胞免受H2O2、6-羟基多巴胺和其他抗生物素药物等神经毒剂的侵害，并抑制了脂多糖（LPS）诱导的NO过度产生。其中，化合物6.22具有在低浓度下（2.5μM）表现出强烈抗氧化活性（细胞存活率＝94.5%）特点。此外，化合物6.22（IC50＝1.6μM）的抗炎活性略强于基准化合物1（IC50＝13.4μM）。鉴于6.22在性能上的突出表现，检测了H2O2损伤的PC12细胞的凋亡率，通过附着抑制器V-FITC/PI试剂，结果表明在低浓度（2.5μM）下，6.22的抗凋亡活性比基准化合物1更高，这与抗氧化和抗炎作用类似。此外，基于计算预测其中枢神经系统的(+)和血脑屏障（BBB）通透性（P-e＝6.84×10（-6） cm s（-1）），具有较低的细胞毒性以及良好的物化性质，因此，化合物6.22可以进一步开发为一种潜在多功能神经保护剂。（C）2019 Elsevier Masson SAS. 版权所有。

  DOI：

  10.1016/j.ejmech.2019.03.044
• 作为产物：
  描述：

  1-癸硫醇 在 potassium permanganate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 14.5h， 生成 2-(undecylsulfonyl)acetic acid
  参考文献：
  名称：

  Immunosuppressive but Non-LasR-Inducing Analogues of the Pseudomonas aeruginosa Quorum-Sensing Molecule N-(3-Oxododecanoyl)-l-homoserine Lactone

  摘要：

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.

  DOI：

  10.1021/jm2001019

文献信息

• Smith; Hernestam, Acta Chemica Scandinavica (1947), 1954, vol. 8, p. 1111,1116,1118
  作者：Smith、Hernestam

  DOI：——

  日期：——
• Structure-activity relationship studies of (E)-3,4-dihydroxystyryl alkyl sulfones as novel neuroprotective agents based on improved antioxidant, anti-inflammatory activities and BBB permeability
  作者：Ying Chen、Bolin Wu、Yameng Hao、Yunqi Liu、Zhili Zhang、Chao Tian、Xianling Ning、Ying Guo、Junyi Liu、Xiaowei Wang

  DOI：10.1016/j.ejmech.2019.03.044

  日期：2019.6

  (E)-3,4-dihydroxystyryl alkyl sulfones, as new analogues of neurodegenerative agents, were designed and synthesized. The biological results demonstrated that most of the target compounds preserved antioxidant and anti-inflammatory potency in scavenging reactive free radicals, protecting neuronal cells against neurotoxins such as H2O2, 6-hydroxydopamine and inhibiting lipopolysaccharide (LPS)-induced over-production of NO. Among these compounds, 6.22 with cyclopentyl propyl exhibited prominent antioxidant activity at low concentration (2.5 mu M) in H2O2 model (cell viability = 94.5%). In addition, 6.22 (IC50 = 1.6 mu M) displayed better anti-inflammatory activity than that of lead compound 1 (IC50 = 13.4 mu M). In view of the outstanding performance of 6.22, the apoptotic rates of H2O2-damaged PC12 cells were detected by Annexin V-FITC/PI assay. 6.22 showed higher potency in inhibition of apoptosis than 1 at low concentration (2.5 mu M), consisting with the antioxidant and anti-inflammatory models. Furthermore, with the predicted CNS (+) blood-brain barrier (BBB) permeability (P-e = 6.84 x 10(-6) cm s(-1)),low cytotoxicity and favorable physiochemical properties based on calculation, compound 6.22 can be further developed as a potential multifunctional neuroprotective agent. (C) 2019 Elsevier Masson SAS. All rights reserved.

  （E）-3,4-双羟基苯基甲基硫醚作为神经退行性疾病药的新类同代物被设计并合成。生物测试结果表明，在清除自由基以及抗炎性反应中，大多数目标化合物保持了抗氧化和抗炎活性，从而保护神经细胞免受H2O2、6-羟基多巴胺和其他抗生物素药物等神经毒剂的侵害，并抑制了脂多糖（LPS）诱导的NO过度产生。其中，化合物6.22具有在低浓度下（2.5μM）表现出强烈抗氧化活性（细胞存活率＝94.5%）特点。此外，化合物6.22（IC50＝1.6μM）的抗炎活性略强于基准化合物1（IC50＝13.4μM）。鉴于6.22在性能上的突出表现，检测了H2O2损伤的PC12细胞的凋亡率，通过附着抑制器V-FITC/PI试剂，结果表明在低浓度（2.5μM）下，6.22的抗凋亡活性比基准化合物1更高，这与抗氧化和抗炎作用类似。此外，基于计算预测其中枢神经系统的(+)和血脑屏障（BBB）通透性（P-e＝6.84×10（-6） cm s（-1）），具有较低的细胞毒性以及良好的物化性质，因此，化合物6.22可以进一步开发为一种潜在多功能神经保护剂。（C）2019 Elsevier Masson SAS. 版权所有。
• Immunosuppressive but Non-LasR-Inducing Analogues of the <i>Pseudomonas aeruginosa</i> Quorum-Sensing Molecule <i>N</i>-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone
  作者：Gopal P. Jadhav、Siri Ram Chhabra、Gary Telford、Doreen S. W. Hooi、Karima Righetti、Paul Williams、Barrie Kellam、David I. Pritchard、Peter M. Fischer

  DOI：10.1021/jm2001019

  日期：2011.5.12

  The Pseudomonas aeruginosa quorum-sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone (1) is involved not only in bacterial activation but also in subversion of the host immune system, and this compound might thus be used as a template to design immunosuppressive agents, provided derivatives devoid of quorum-sensing activity could be discovered. By use of a leukocyte proliferation assay and a newly developed bioluminescent P. aeruginosa reporter assay, systematic modification of 1 allowed us to delineate the bacterial LasR-induction and host immunosuppressive activities. The main determinant is replacement of the methylene group proximal to the beta-ketoamide in the acyl chain of 1 with functions containing heteroatoms, especially an NH group. This modification can be combined with replacement of the homoserine lactone system in 1 with stable cyclic groups. For example, we found the simple compound N(1)-(5-chloro-2-hydroxyphenyl)-N(3)-octylmalonamide (25d) to be over twice as potent as 1 as an immune suppressor while displaying LasR-induction antagonist activity.