2-(3,4-dimethoxybenzamido)-5-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,4-dimethoxybenzamido)-5-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-[(3,4-dimethoxybenzoyl)amino]-5-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• 化学式: C₂₁H₂₅NO₅S
• 分子量: 403.499
• InChiKey: ALFCPWHSVYARHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氰乙酸乙酯 、 3-甲基环己酮 在 吗啉 、 sulfur 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 2-(3,4-dimethoxybenzamido)-5-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure-Based Virtual Screening, Compound Synthesis, and Bioassay for the Design of Chitinase Inhibitors

  摘要：

  Chitinases play a vital part in the molting phase of insect pests. Inhibiting their activities by the use of drug-like small chemical molecules is thought to be an efficient strategy in pesticide design and development. On the basis of the crystal structure of Of ChtI, a chitinase indispensable for the molting of the insect pest Ostrinia furnacalis (Asian corn borer), here we report a chemical fragment and five variant compounds as inhibitors of Of ChtI obtained from a library of over 200 000 chemicals by a structure-based-virtual-screening approach. The compounds were synthesized with high atom economy and tested for their. Of ChtI-inhibitory activities in a bioassay. Compound 3 showed preferential inhibitory activity with a K-i value of 1.5 mu M against Of ChtI. Analysis of the structure-activity relationships of the compounds provided insight into their interactions with the enzyme active site, which may inform future work in improving the potencies of their inhibitory activities.

  DOI：

  10.1021/acs.jafc.8b00017

文献信息

• Structure-Based Virtual Screening, Compound Synthesis, and Bioassay for the Design of Chitinase Inhibitors
  作者：Yawen Dong、Xi Jiang、Tian Liu、Yun Ling、Qing Yang、Li Zhang、Xiongkui He

  DOI：10.1021/acs.jafc.8b00017

  日期：2018.4.4

  Chitinases play a vital part in the molting phase of insect pests. Inhibiting their activities by the use of drug-like small chemical molecules is thought to be an efficient strategy in pesticide design and development. On the basis of the crystal structure of Of ChtI, a chitinase indispensable for the molting of the insect pest Ostrinia furnacalis (Asian corn borer), here we report a chemical fragment and five variant compounds as inhibitors of Of ChtI obtained from a library of over 200 000 chemicals by a structure-based-virtual-screening approach. The compounds were synthesized with high atom economy and tested for their. Of ChtI-inhibitory activities in a bioassay. Compound 3 showed preferential inhibitory activity with a K-i value of 1.5 mu M against Of ChtI. Analysis of the structure-activity relationships of the compounds provided insight into their interactions with the enzyme active site, which may inform future work in improving the potencies of their inhibitory activities.