sodium hydroxy(2,3,4-trimethoxyphenyl)methanesulfonate | 949490-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: sodium hydroxy(2,3,4-trimethoxyphenyl)methanesulfonate
• 英文别名: Sodium;hydroxy-(2,3,4-trimethoxyphenyl)methanesulfonate；sodium;hydroxy-(2,3,4-trimethoxyphenyl)methanesulfonate
• CAS: 949490-29-3
• 化学式: C₁₀H₁₃O₇S*Na
• 分子量: 300.265
• InChiKey: PILKGNHXXCSNBR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.75
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium hydroxy(2,3,4-trimethoxyphenyl)methanesulfonate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-(2-(2,3,4-trimethoxyphenyl)-1H-benzimidazol-5-yl)ethanol
  参考文献：
  名称：

  5-Acetyl-2-arylbenzimidazoles as antiviral agents. Part 4

  摘要：

  Within a project aimed at discovering new Flaviviridae inhibitors, new variously substituted 2-phenylbenzimidazoles were synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against viruses representatives of the three genera of the Flaviviridae family, i.e.: Pestivirus (BVDV), Flavivirus (YFV) and Hepacivirus (HCV). Title compounds were also tested against RNA viruses representative of other single-stranded, positive-sense (ssRNA(+)) negative-sense (RNA(-)), or double-stranded (dsRNA) genomes, as well as against representatives of two DNA virus families.Nine compounds showed activity against BVDV (EC50 = 0.8-8.0 mu M), compound 31 being the most potent (EC50 = 0.80 mu M) and selective (SI = CC50/EC50 = >100). When tested in an HCV replicon assay, compound 31 resulted again the most potent, displaying an EC50 value of 1.11 mu M and an SI of 100. Besides inhibiting BVDV, two compounds (35 and 38) showed a moderate activity also against YFV (EC50 = 13 mu M). Interestingly, 35 was moderately active also against RSV (EC50 = 25 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.038
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 sodium metabisulfite 作用下， 以 乙醇 、 水 为溶剂， 以98%的产率得到sodium hydroxy(2,3,4-trimethoxyphenyl)methanesulfonate
  参考文献：
  名称：

  亚硫酸氢盐加成化合物作为水中还原胺化的底物

  摘要：

  可以在水性胶束催化条件下制备由醛的耐贮存亚硫酸氢盐加成化合物还原胺化产生的高价值产品。容易获得的 α-甲基吡啶硼烷用作化学计量氢化物源。水性反应介质的回收很容易实现，并且记录了在制药工业中对目标的几种应用。

  DOI：

  10.1021/acs.orglett.1c02604

文献信息

• Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives
  作者：Michele Tonelli、Matteo Simone、Bruno Tasso、Federica Novelli、Vito Boido、Fabio Sparatore、Giuseppe Paglietti、Sabrina Pricl、Gabriele Giliberti、Sylvain Blois、Cristina Ibba、Giuseppina Sanna、Roberta Loddo、Paolo La Colla

  DOI：10.1016/j.bmc.2010.02.037

  日期：2010.4

  Seventy-six 2-phenylbenzimidazole derivatives were synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of 10 RNA and DNA viruses. The most commonly affected viruses were, in decreasing order, CVB-2, BVDV, Sb-1, HSV-1, and YFV, while HIV-1 and VSV were not affected, and RSV, VV and Reo-1 were only susceptible to a few compounds. Thirty-nine compounds

  合成了76种2-苯基苯并咪唑衍生物，并在基于细胞的测定中评估了其对一组10种RNA和DNA病毒的细胞毒性和抗病毒活性。受影响最严重的病毒以降序排列，分别是CVB-2，BVDV，Sb-1，HSV-1和YFV，而HIV-1和VSV不受影响，RSV，VV和Reo-1仅易感一些化合物。39种化合物表现出 对至少一种病毒的高活性（EC 50 = 0.1–10μM），其中四种对VV（24，EC 50  = 0.1μM）和BVDV（50，具有EC 50的51和53 分别为1.5、0.8和1.0μM）。最后的化合物在低微摩尔浓度下抑制BVDV和HCV的NS5B RdRp，后者与前者具有结构相似性。所考虑的化合物代表了针对痘病毒，瘟病毒甚至HCV（它们是重要的人类和兽医病原体）的抗病毒剂开发的诱人线索。
• Bisulfite Addition Compounds as Substrates for Reductive Aminations in Water
  作者：Xiaohan Li、Karthik S. Iyer、Ruchita R. Thakore、David K. Leahy、J. Daniel Bailey、Bruce H. Lipshutz

  DOI：10.1021/acs.orglett.1c02604

  日期：2021.9.17

  Highly valued products resulting from reductive aminations utilizing shelf-stable bisulfite addition compounds of aldehydes can be made under aqueous micellar catalysis conditions. Readily available α-picolineborane serves as the stoichiometric hydride source. Recycling of the aqueous reaction medium is easily accomplished, and several applications to targets in the pharmaceutical industry are documented

  可以在水性胶束催化条件下制备由醛的耐贮存亚硫酸氢盐加成化合物还原胺化产生的高价值产品。容易获得的 α-甲基吡啶硼烷用作化学计量氢化物源。水性反应介质的回收很容易实现，并且记录了在制药工业中对目标的几种应用。
• 5-Acetyl-2-arylbenzimidazoles as antiviral agents. Part 4
  作者：Gabriella Vitale、Paola Corona、Mario Loriga、Antonio Carta、Giuseppe Paglietti、Gabriele Giliberti、Giuseppina Sanna、Pamela Farci、Maria Elena Marongiu、Paolo La Colla

  DOI：10.1016/j.ejmech.2012.03.038

  日期：2012.7

  Within a project aimed at discovering new Flaviviridae inhibitors, new variously substituted 2-phenylbenzimidazoles were synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against viruses representatives of the three genera of the Flaviviridae family, i.e.: Pestivirus (BVDV), Flavivirus (YFV) and Hepacivirus (HCV). Title compounds were also tested against RNA viruses representative of other single-stranded, positive-sense (ssRNA(+)) negative-sense (RNA(-)), or double-stranded (dsRNA) genomes, as well as against representatives of two DNA virus families.Nine compounds showed activity against BVDV (EC50 = 0.8-8.0 mu M), compound 31 being the most potent (EC50 = 0.80 mu M) and selective (SI = CC50/EC50 = >100). When tested in an HCV replicon assay, compound 31 resulted again the most potent, displaying an EC50 value of 1.11 mu M and an SI of 100. Besides inhibiting BVDV, two compounds (35 and 38) showed a moderate activity also against YFV (EC50 = 13 mu M). Interestingly, 35 was moderately active also against RSV (EC50 = 25 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.