Acetic acid 5-(4-benzylsulfanyl-but-1-ynyl)-2-methoxy-phenyl ester | 445483-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Acetic acid 5-(4-benzylsulfanyl-but-1-ynyl)-2-methoxy-phenyl ester
• 英文别名: Benzyl 4-(3'-acetoxy-4'-methoxyphenyl)-3-butynyl sulfide；[5-(4-benzylsulfanylbut-1-ynyl)-2-methoxyphenyl] acetate
• CAS: 445483-19-2
• 化学式: C₂₀H₂₀O₃S
• 分子量: 340.443
• InChiKey: DLBOUJRRJLANFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid 5-(4-benzylsulfanyl-but-1-ynyl)-2-methoxy-phenyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 碘 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-methoxy-5-[3-(3,4,5-trimethoxy-phenyl)-4,5-dihydro-thiophen-2-yl]-phenol
  参考文献：
  名称：

  The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4

  摘要：

  A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed. a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3 5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than I but exhibit comparable activity to the most active of the benzo[b]thiophenes 3 5. A structure-activity relationship or these compounds is considered. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00436-x
• 作为产物：
  描述：

  5-iodo-2-methoxyphenyl acetate 、 4-(benzylthio)-1-butyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到Acetic acid 5-(4-benzylsulfanyl-but-1-ynyl)-2-methoxy-phenyl ester
  参考文献：
  名称：

  The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4

  摘要：

  A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed. a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3 5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than I but exhibit comparable activity to the most active of the benzo[b]thiophenes 3 5. A structure-activity relationship or these compounds is considered. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00436-x

文献信息

• [EN] SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS<br/>[FR] SYNTHESE DESTINEE A LA PREPARATION DE COMPOSES DE CRIBLAGE UTILISES COMME AGENTS DE FIXATION A LA TUBULINE
  申请人：UNIV AUSTRALIAN

  公开号：WO2002060872A1

  公开（公告）日：2002-08-08

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物以用作潜在的微管聚合抑制剂筛选的方法。本发明还提供了具有微管聚合抑制剂活性的化学化合物。
• Synthesis for the preparation of compounds for screening as potential tubulin binding agents
  申请人：Flynn Luke Bernard

  公开号：US20050130221A1

  公开（公告）日：2005-06-16

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物的方法，用于筛选作为潜在微管聚合抑制剂的化合物。本发明还提供具有微管聚合抑制剂活性的化学化合物。
• SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS
  申请人：THE AUSTRALIAN NATIONAL UNIVERSITY

  公开号：EP1363880A1

  公开（公告）日：2003-11-26
• EP1363880A4
  申请人：——

  公开号：EP1363880A4

  公开（公告）日：2008-10-08