6-methoxybenzo[b]thiophene-3-carbaldehyde | 896722-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-methoxybenzo[b]thiophene-3-carbaldehyde
• 英文别名: 6-Methoxybenzo[b]thiophene-3-carbaldehyde；6-methoxy-1-benzothiophene-3-carbaldehyde
• CAS: 896722-64-8
• 化学式: C₁₀H₈O₂S
• 分子量: 192.238
• InChiKey: OFVKREZVYRTNOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxybenzo[b]thiophene-3-carbaldehyde 在 硫酸 、 碘 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Development of a Novel Class of Tubulin Inhibitor from Desmosdumotin B with a Hydroxylated Bicyclic B-Ring

  摘要：

  A series of newly synthesized hydroxylated analogues of triethyldesmosdumotin B (TEDB) with a bicyclic B-ring exhibited a significantly different mode of action for affecting microtubule dynamics and spindle formation but had the same antiproliferative activity spectrum, including activity against multidrug-resistant tumors. These analogues efficiently induced cell cycle arrest at prometaphase and caused formation of immature multipolar spindles. 6'-Hydroxyl TEDB-TB (8) disrupted bipolar spindle formation but had a negligible effect on interphase microtubules. On the basis of the predicted binding modes of the new compounds with tubulin dimer, compound 4 forms three hydrogen bonds (H-bonds) only with alpha-tubulin at the colchicine site; in contrast, 8 forms H-bonds with both alpha- and beta-tubulin. We predict that, when a compound/ligand, such as 8, forms H-bonds to both alpha- and beta-tubulins, spindle formation is disrupted more than the dynamics of interphase microtubules. This result may reflect the well-known greater dynamicity of spindle microtubules as compared with interphase microtubules.

  DOI：

  10.1021/jm501859j
• 作为产物：
  描述：

  3-甲氧基苯硫酚 在 N-溴代丁二酰亚胺(NBS) 、 乌洛托品 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 6-methoxybenzo[b]thiophene-3-carbaldehyde
  参考文献：
  名称：

  Development of a Novel Class of Tubulin Inhibitor from Desmosdumotin B with a Hydroxylated Bicyclic B-Ring

  摘要：

  A series of newly synthesized hydroxylated analogues of triethyldesmosdumotin B (TEDB) with a bicyclic B-ring exhibited a significantly different mode of action for affecting microtubule dynamics and spindle formation but had the same antiproliferative activity spectrum, including activity against multidrug-resistant tumors. These analogues efficiently induced cell cycle arrest at prometaphase and caused formation of immature multipolar spindles. 6'-Hydroxyl TEDB-TB (8) disrupted bipolar spindle formation but had a negligible effect on interphase microtubules. On the basis of the predicted binding modes of the new compounds with tubulin dimer, compound 4 forms three hydrogen bonds (H-bonds) only with alpha-tubulin at the colchicine site; in contrast, 8 forms H-bonds with both alpha- and beta-tubulin. We predict that, when a compound/ligand, such as 8, forms H-bonds to both alpha- and beta-tubulins, spindle formation is disrupted more than the dynamics of interphase microtubules. This result may reflect the well-known greater dynamicity of spindle microtubules as compared with interphase microtubules.

  DOI：

  10.1021/jm501859j

文献信息

• Anti-tumor compounds
  申请人：Hsieh Hsing-Pang

  公开号：US20060148801A1

  公开（公告）日：2006-07-06

  Compounds of the following formula: wherein A, D, Q, T, U, V, W, X, Y, Z, R 1 , and ---- are as defined herein. This invention also relates to a method of inhibiting tubulin polymerization, or treating cancer or an angiogenesis-related disorder with one of these compounds.

  以下化合物的结构如下： 其中A、D、Q、T、U、V、W、X、Y、Z、R1和----在此处定义。本发明还涉及一种通过其中一种化合物抑制微管聚合，或治疗癌症或血管生成相关疾病的方法。
• ANTI-TUMOR COMPOUNDS
  申请人：National Health Research Institutes

  公开号：EP1838711A2

  公开（公告）日：2007-10-03
• US7456289B2
  申请人：——

  公开号：US7456289B2

  公开（公告）日：2008-11-25
• [EN] ANTI-TUMOR COMPOUNDS<br/>[FR] COMPOSES ANTITUMORAUX
  申请人：NAT HEALTH RESEARCH INSTITUTES

  公开号：WO2006074041A2

  公开（公告）日：2006-07-13

  [EN] Compounds of formula (I); wherein A, D, Q, T, U, V, W, X, Y, Z, R₁, and formula (II) are as defined herein. This invention also relates to a method of inhibiting tubulin polymerization, or treating cancer or an angiogenesis-related disorder with one of these compounds.
  [FR] L'invention porte sur des composés de formule (I) dans laquelle A, D, Q, T, U, V, W, X, Y, Z, R₁, et de formule (II) qui sont tels que définis dans la demande. Cette invention porte également sur une méthode d'inhibition de la polymérisation de la tubuline ou du traitement du cancer ou d'une maladie liée à l'angiogenèse avec l'un de ces composés.
• Development of a Novel Class of Tubulin Inhibitor from Desmosdumotin B with a Hydroxylated Bicyclic B-Ring
  作者：Kyoko Nakagawa-Goto、Akifumi Oda、Ernest Hamel、Emika Ohkoshi、Kuo-Hsiung Lee、Masuo Goto

  DOI：10.1021/jm501859j

  日期：2015.3.12

  A series of newly synthesized hydroxylated analogues of triethyldesmosdumotin B (TEDB) with a bicyclic B-ring exhibited a significantly different mode of action for affecting microtubule dynamics and spindle formation but had the same antiproliferative activity spectrum, including activity against multidrug-resistant tumors. These analogues efficiently induced cell cycle arrest at prometaphase and caused formation of immature multipolar spindles. 6'-Hydroxyl TEDB-TB (8) disrupted bipolar spindle formation but had a negligible effect on interphase microtubules. On the basis of the predicted binding modes of the new compounds with tubulin dimer, compound 4 forms three hydrogen bonds (H-bonds) only with alpha-tubulin at the colchicine site; in contrast, 8 forms H-bonds with both alpha- and beta-tubulin. We predict that, when a compound/ligand, such as 8, forms H-bonds to both alpha- and beta-tubulins, spindle formation is disrupted more than the dynamics of interphase microtubules. This result may reflect the well-known greater dynamicity of spindle microtubules as compared with interphase microtubules.