6-Methoxy-3-methyl-benzothiophen | 27514-15-4

• 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-Methoxy-3-methyl-benzothiophen
• 英文别名: 6-methoxy-3-methylbenzo[b]thiophene；6-methoxy-3-methyl-1-benzothiophene
• CAS: 27514-15-4
• 化学式: C₁₀H₁₀OS
• 分子量: 178.255
• InChiKey: GJCYIQPHWUNADU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Methoxy-3-methyl-benzothiophen 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以80%的产率得到6-methoxybenzo[b]thiophene-3-carbaldehyde
  参考文献：
  名称：

  Anti-tumor compounds

  摘要：

  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。

  公开号：

  US20060148801A1
• 作为产物：
  描述：

  3-甲氧基苯硫酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 6-Methoxy-3-methyl-benzothiophen
  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

• Versatile Synthesis of Benzothiophenes and Benzoselenophenes by Rapid Assembly of Arylzinc Reagents, Alkynes, and Elemental Chalcogens
  作者：Bin Wu、Naohiko Yoshikai

  DOI：10.1002/anie.201304546

  日期：2013.9.27

  Rapidly aSSembled: The combination of cobalt‐catalyzed migratory arylzincation and copper‐mediated/catalyzed chalcogenative cyclization allows the construction of benzothiophenes and benzoselenophenes from arylzinc reagents, alkynes, and elemental chalcogens. Benzothiophenes and benzoselenophenes diversely functionalized at the benzene ring moiety can be prepared, which are not readily accessible by

  快速组装：钴催化的迁移性芳基化与铜介导/催化的硫属元素化环化相结合，可以从芳基锌试剂，炔烃和元素硫属元素化合物中构建苯并噻吩和苯并硒基苯。可以制备在苯环部分被不同功能化的苯并噻吩和苯并硒吩，这是常规方法不易获得的。
• 2,3-Dihydro-6-nitroimidazo[2,1-b]oxazoles
  申请人：Tsubouchi Hidetsugu

  公开号：US20060094767A1

  公开（公告）日：2006-05-04

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R 1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R 2 represents a group —OR 3 or the like, and R 3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R 1 and —(CH 2 ) n R 2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R 41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis , multi-drug-resistant Mycobacterium tuberculosis , and atypical acid-fast bacteria.

  本发明提供了一种2,3-二氢-6-硝基咪唑并[2,1-b]噁唑化合物，其通式如下：其中，R1代表氢原子或C1-C6烷基，n代表0到6的整数，R2代表—OR3或类似的基团，R3代表氢原子、C1-C6烷基或类似的基团，或者R1和—(CH2)nR2可以通过相邻的碳原子通过氮原子结合在一起形成一个螺环，其通式为（H）：其中，R41为氢、C1-C6烷基或类似的基团。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型酸性快速细菌具有优异的杀菌作用。
• 2,3-DIHYDRO-6-NITROIMIDAZO 2,1-b OXAZOLES
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP1555267A1

  公开（公告）日：2005-07-20

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R2 represents a group -OR3 or the like, and R3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R1 and -(CH2)nR2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and a typical acid-fast bacteria.

  本发明提供了由以下通式代表的 2，3-二氢-6-硝基咪唑并[2，1-b]恶唑化合物： 其中R1代表氢原子或C1-C6烷基，n代表0至6的整数，R2代表基团-OR3或类似基团，R3代表氢原子、C1-C6烷基或类似基团，或者R1和-(CH2)nR2可以通过氮原子与相邻的碳原子相互结合，从而形成通式(H)代表的螺环： 其中 R41 为氢、C1-C6 烷基或类似基团。本化合物对结核分枝杆菌、多重耐药结核分枝杆菌和典型的耐酸细菌有很好的杀菌作用。
• 2,3-dihydro-6-nitroimidazo[2,1-b]oxazoles compound
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP2570418A2

  公开（公告）日：2013-03-20

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R2 represents a group -OR3 or the like, and R3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R1 and -(CH2)nR2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and atypical acid-fast bacteria.

  本发明提供了一种由以下通式表示的 2,3-二氢-6-硝基咪唑并[2,1-b]恶唑化合物： 其中R1代表氢原子或C1-C6烷基，n代表0至6的整数，R2代表基团-OR3或类似基团，R3代表氢原子、C1-C6烷基或类似基团，或者R1和-(CH2)nR2可以通过氮原子与相邻的碳原子相互结合，从而形成通式(H)代表的螺环： 其中 R41 为氢、C1-C6 烷基或类似基团。本化合物对结核分枝杆菌、多重耐药结核分枝杆菌和非典型耐酸菌有很好的杀菌作用。
• Advances toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 1
  作者：Kumiko Takeuchi、Todd J Kohn、Nicholas A Honigschmidt、Vincent P Rocco、Patrick G Spinazze、Daniel J Koch、David L Nelson、D.Bradley Wainscott、Laura J Ahmad、Janice Shaw、Penny G Threlkeld、David T Wong

  DOI：10.1016/s0960-894x(03)00303-2

  日期：2003.6

  A series of 1-aryloxy-3-piperidinylpropan-2-ols possessing potent dual 5-HT1A receptor antagonism and serotonin reuptake inhibition was discovered. 1-(4H-Indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols exhibited selective and high affinity at the 5-HT1A receptor and serotonin reuptake inhibition at nanomolar concentrations for dual activities. (C) 2003 Elsevier Science Ltd. All rights reserved.