bis(3,4,5-trimethoxyphenyl)disulfide | 16807-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: bis(3,4,5-trimethoxyphenyl)disulfide
• 英文别名: 1,1'-(3,4,5-trimethoxyphenyl)disulfide；Di-(3,4,5-Trimethoxyphenyl)-disulfid；1,2,3-trimethoxy-5-[(3,4,5-trimethoxyphenyl)disulfanyl]benzene
• CAS: 16807-29-7
• 化学式: C₁₈H₂₂O₆S₂
• 分子量: 398.501
• InChiKey: YMVGXEOYSWMCKV-UHFFFAOYSA-N

物化性质

• 熔点：
  135-145 °C(Solv: ethanol (64-17-5))
• 沸点：
  494.5±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis(3,4,5-trimethoxyphenyl)disulfide 在 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 5,6-dimethoxy-3-(3,4,5-trimethoxy-phenylthio)-1H-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  1-benzyl-3-thioaryl-2-carboxyindoles as potent non-peptide endothelin antagonists

  摘要：

  Endothelin-1 is a potent vasoconstrictor which is thought to be involved in many human disease states. We have developed a series of indole non-peptide endothelin antagonists which display nanomolar receptor affinity. The representative compound from this series is PD 159433 (22), an ET(A) selective antagonist with an IC50 of 2 nM. The discovery, synthesis and structure-activity relationships of this series of compounds are described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00232-6
• 作为产物：
  描述：

  3,4,5-三甲氧基苯胺 生成 bis(3,4,5-trimethoxyphenyl)disulfide
  参考文献：
  名称：

  抗疟药。4,4'-二氨基二苯砜型化合物。

  摘要：

  DOI：

  10.1021/jm00296a049

文献信息

• Aerobic Oxidative C–H Azolation of Indoles and One-Pot Synthesis of Azolyl Thioindoles by Flavin–Iodine-Coupled Organocatalysis
  作者：Kazumasa Tanimoto、Hayaki Okai、Marina Oka、Ryoma Ohkado、Hiroki Iida

  DOI：10.1021/acs.orglett.1c00241

  日期：2021.3.19

  The aerobic oxidative cross-coupling of indoles with azoles driven by flavin-iodine-coupled organocatalysis has been developed for the green synthesis of 2-(azol-1-yl)indoles. The coupled organocatalytic system enabled the one-pot three-component synthesis of 2-azolyl-3-thioindoles from indoles, azoles, and thiols in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent

  已开发了由黄素-碘偶联的有机催化驱动的吲哚与唑类的需氧氧化交叉偶联，用于2-（azol-1-yl）吲哚的绿色合成。偶联的有机催化系统通过利用分子氧作为唯一的牺牲试剂，以原子经济的方式从吲哚，唑类和硫醇一锅法合成2-偶氮基-3-硫代吲哚。
• New 6- and 7-heterocyclyl-1H-indole derivatives as potent tubulin assembly and cancer cell growth inhibitors
  作者：Giuseppe La Regina、Ruoli Bai、Antonio Coluccia、Valentina Naccarato、Valeria Famiglini、Marianna Nalli、Domiziana Masci、Annalisa Verrico、Paola Rovella、Carmela Mazzoccoli、Eleonora Da Pozzo、Chiara Cavallini、Claudia Martini、Stefania Vultaggio、Giulio Dondio、Mario Varasi、Ciro Mercurio、Ernest Hamel、Patrizia Lavia、Romano Silvestri

  DOI：10.1016/j.ejmech.2018.04.042

  日期：2018.5

  designed new 3-arylthio- and 3-aroyl-1H-indole derivatives 3-22 bearing a heterocyclic ring at position 5, 6 or 7 of the indole nucleus. The 6- and 7-heterocyclyl-1H-indoles showed potent inhibition of tubulin polymerization, binding of colchicine to tubulin and growth of MCF-7 cancer cells. Compounds 13 and 19 inhibited a panel of cancer cells and the NCI/ADR-RES multidrug resistant cell line at low

  我们设计了新的3-芳硫基和3-芳基-1H-吲哚衍生物3-22，其在吲哚核的5、6或7位带有杂环。6-和7-杂环基-1H-吲哚显示出对微管蛋白聚合的有效抑制，秋水仙碱与微管蛋白的结合以及MCF-7癌细胞的生长。化合物13和19在低纳摩尔浓度下抑制了一组癌细胞和NCI / ADR-RES多药耐药细胞系。浓度为50 nM的化合物13在HeLa细胞中诱导77％的G2 / M，浓度为20 nM时引起50％的有丝分裂稳定停滞。作为HepG2细胞的抑制剂（IC50 = 20 nM），13的毒性是19的4倍。化合物13是纳摩尔浓度的人U87MG胶质母细胞瘤细胞的有效抑制剂，比以前报道的芳基硫代吲哚高出近一个数量级。
• [EN] INDOLIC DERIVATIVES AND USE THEREOF IN MEDICAL FIELD<br/>[FR] DÉRIVÉS INDOLIQUES ET UTILISATION DE CELLES-CI DANS LE DOMAINE MÉDICAL
  申请人：UNI DEGLI STUDI DL ROMA LA SAPIENZA

  公开号：WO2011121629A1

  公开（公告）日：2011-10-06

  The present invention concerns indolic derivatives and use thereof in medical field. Particularly, the invention concerns 3-[(3',4',5'- trimethoxyphenyl)thio]-1 H-indole derivatives and bioisosteric derivatives thereof and their use for the treatment of tumours.

  本发明涉及吲哚衍生物及其在医学领域中的应用。具体而言，该发明涉及3-[(3',4',5'-三甲氧基苯基)硫基]-1 H-吲哚衍生物及其生物同位素衍生物，以及它们在肿瘤治疗中的应用。
• [EN] ARYLTHIOINDOLE TUBULIN POLYMERIZATION INHIBITORS AND METHODS OF TREATING OR PREVENTING CANCER USING SAME<br/>[FR] INHIBITEURS DE LA POLYMERISATION DE LA TUBULINE DE TYPE ARYLTHIOINDOLE, ET PROCEDES POUR TRAITER OU PREVENIR UN CANCER AU MOYEN DE CES INHIBITEURS
  申请人：HUMAN SERVICES GOVERNMENT OF T

  公开号：WO2006041961A1

  公开（公告）日：2006-04-20

  The present invention features arylthioindole compounds, pharmaceutical compositions of arylthioindole compounds and methods of treating a patient suffering from cancer or inflammatory, cardiac, or helminthic diseases, the method comprising administering to a patient one or more arylthioindole compounds of the invention.

  本发明涉及芳基硫代吲哚化合物，芳基硫代吲哚化合物的药物组合物以及治疗患有癌症或炎症、心脏病或寄生虫病的患者的方法，该方法包括向患者施用本发明的一种或多种芳基硫代吲哚化合物。
• Arylthioindoles, Potent Inhibitors of Tubulin Polymerization
  作者：Gabriella De Martino、Giuseppe La Regina、Antonio Coluccia、Michael C. Edler、Maria Chiara Barbera、Andrea Brancale、Elizabeth Wilcox、Ernest Hamel、Marino Artico、Romano Silvestri

  DOI：10.1021/jm049360d

  日期：2004.12.1

  Several arylthioindoles had excellent activity as inhibitors both of tubulin polymerization and of the growth of MCF-7 human breast carcinoma cells. Methyl 3-[(3,4,5-trimethoxyphenyl)thio]-5-methoxy-1H-indole-2-carboxylate (21), the most potent derivative, showed IC(50) = 2.0 microM, 1.6 times more active than colchicine and about as active as combretastatin A-4 (CSA4). Compound 21 inhibited the growth

  几种芳基硫代吲哚作为微管蛋白聚合和MCF-7人乳腺癌细胞生长的抑制剂均具有出色的活性。最有效的衍生物3-[（3,4,5-三甲氧基苯基）硫代] -5-甲氧基-1H-吲哚-2-羧酸甲酯（21）的IC（50）= 2.0 microM，活性是其1.6倍秋水仙碱，其活性与康维他汀A-4（CSA4）差不多。化合物21在IC（50）= 13 nM时抑制了MCF-7细胞的生长。秋水仙碱和CSA4与这些细胞分别具有13 nM和17 nM IC（50）值。