4,7-Dimethylbenzothiophene-3(2H)-one | 104247-65-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,7-Dimethylbenzothiophene-3(2H)-one
• 英文别名: 4,7-dimethylbenzothiophen-3(2H)-one；4,7-Di-methylbenzothiophene-3(2h)-one；4,7-dimethyl-1-benzothiophen-3-one
• CAS: 104247-65-6
• 化学式: C₁₀H₁₀OS
• 分子量: 178.255
• InChiKey: DKQISDCTFYTQPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,7-Dimethylbenzothiophene-3(2H)-one 在 哌啶 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 1,4-Dimethyl-11-thia-5-aza-benzo[b]fluorene-6-carboxylic acid (2-dimethylamino-ethyl)-amide
  参考文献：
  名称：

  Synthesis of Substituted Indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides: Evaluation of Structure–Activity Relationships for Cytotoxicity

  摘要：

  New substituted indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides were prepared from methyl 2-amino-3-formylbenzoate by a new Friedlander synthesis. Evaluation of these carboxamides for cytotoxicity in a panel of cell lines showed that small lipophilic substituents in the non-carboxamide ring, in a pseudo-peri position to the side chain, significantly increased cytotoxic potency while retaining a pattern of cytotoxicity consistent with a non-topo II mode of action. The methyl substituted indeno[1,2-b]quinoline-6-carboxamide demonstrated substantial effectiveness (20-day growth delays) in a sub-cutaneous colon 38 in vivo tumor model. This is comparable to that reported for the dual topo I/II inhibitor DACA that is in clinical trial. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00179-6
• 作为产物：
  描述：

  2,5-dimethylthioanisole 、 氯乙酰氯 以57%的产率得到
  参考文献：
  名称：

  KARIMOV, G. K.;USMANOVA, SH. D.;GIZATOVA, B. I.;AKSENOV, V. S.;NUMANOV, I+, DOKL. AN TADZHSSR, 1985, 28, N 6, 347-349

  摘要：

  DOI：

文献信息

• Transformations of six isomers of dimethylbenzothiophene by three Pseudomonas strains
  作者：Kevin G. Kropp、Sanja Saftić、Jan T. Andersson、Phillip M. Fedorak

  DOI：10.1007/bf00058180

  日期：1996.6

  Dimethylbenzothiophenes are among the sulfur heterocycles in petroleum that are known to be degraded by microbial activity. Six of the 15 possible isomers of dimethylbenzothiophene were synthesized and used in biotransformation studies with three Pseudomonas isolates that oxidize a variety of condensed thiophenes including methylbenzothiophenes and methyldibenzothiophenes. The isomers of dimethylbenzothiophene were chosen to have a variety of substitution patterns: both methyl groups on the thiophene ring (the 2,3-isomer); a methyl group on each of the rings (the 2,7-, 3,5- and 3,7-isomers); and both methyl groups on the benzene ring (the 4,6- and 4,7-isomers). Each isolate was grown on l-methylnaphthalene or glucose in the presence of one of the dimethylbenzothiophenes and culture extracts were analyzed to identify nearly 30 sulfur-containing metabolites in total. Sulfoxides and sulfones were commonly found metabolites in culture extracts from the 2,3-, 2,7- and 3,7-isomers, whereas 2,3-diones, 3(2H)-ones and 2(3H)-ones were formed from the 4,6- and 4,7-isomers. High-molecular-weight products, some of which were tentatively identified as tetramethylbenzo[b]naphtho[1,2-d]thiophen were detected in the extracts of cultures incubated with 4,6- or 4,7-dimethylbenzothiophene. The methyl groups of all of the isomers, except 4,6-, were oxidized to give hydroxymethyl-methylbenzothiophenes and methylbenzothiophene-carboxylic acids, and these were the only products detected from the oxidation of 3,5-dimethylbenzothiophene.
• Synthesis of Substituted Indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides: Evaluation of Structure–Activity Relationships for Cytotoxicity
  作者：Junjie Chen、Leslie W. Deady、José Desneves、Anthony J. Kaye、Graeme J. Finlay、Bruce C. Baguley、William A. Denny

  DOI：10.1016/s0968-0896(00)00179-6

  日期：2000.10

  New substituted indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides were prepared from methyl 2-amino-3-formylbenzoate by a new Friedlander synthesis. Evaluation of these carboxamides for cytotoxicity in a panel of cell lines showed that small lipophilic substituents in the non-carboxamide ring, in a pseudo-peri position to the side chain, significantly increased cytotoxic potency while retaining a pattern of cytotoxicity consistent with a non-topo II mode of action. The methyl substituted indeno[1,2-b]quinoline-6-carboxamide demonstrated substantial effectiveness (20-day growth delays) in a sub-cutaneous colon 38 in vivo tumor model. This is comparable to that reported for the dual topo I/II inhibitor DACA that is in clinical trial. (C) 2000 Elsevier Science Ltd. All rights reserved.
• KARIMOV, G. K.;USMANOVA, SH. D.;GIZATOVA, B. I.;AKSENOV, V. S.;NUMANOV, I+, DOKL. AN TADZHSSR, 1985, 28, N 6, 347-349
  作者：KARIMOV, G. K.、USMANOVA, SH. D.、GIZATOVA, B. I.、AKSENOV, V. S.、NUMANOV, I+

  DOI：——

  日期：——