1-(benzo[d]thiazol-2-yl)-4-iodobutan-1-one | 1366349-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 1-(benzo[d]thiazol-2-yl)-4-iodobutan-1-one
• 英文别名: 1-(1,3-Benzothiazol-2-yl)-4-iodobutan-1-one；1-(1,3-benzothiazol-2-yl)-4-iodobutan-1-one
• CAS: 1366349-24-7
• 化学式: C₁₁H₁₀INOS
• 分子量: 331.177
• InChiKey: WMZNNNUDXBNSAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-嘧啶基)哌嗪 、 1-(benzo[d]thiazol-2-yl)-4-iodobutan-1-one 在 potassium carbonate 、 potassium iodide 、 盐酸 作用下， 以 乙腈 为溶剂， 以42%的产率得到1-(benzo[d]thiazol-2-yl)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)butan-1-one dihydrochloride
  参考文献：
  名称：

  Benzothiazoles as probes for the 5HT1A receptor and the serotonin transporter (SERT): A search for new dual-acting agents as potential antidepressants

  摘要：

  The synthesis and evaluation of several benzothiazole-based compounds are described in an attempt to identify novel dual-acting 5HT(1A) receptor and SERT inhibitors as new antidepressants. Binding affinities at the 5HT(1A) receptor and the serotonin transporter do not appear to be congruent and other areas of the binding sites would need to be explored in order to improve binding simultaneously at both sites. Compounds 20 and 23 show moderate binding affinity at the 5HT(1A) receptor and the SERT site and thus, have the potential to be further explored as dual-acting agents. In addition, compound 20 binds with low affinity to the dopamine transporter (DAT), the norepinephrine transporter (NET) and 5HT(2C) receptor, which are desirable properties as selectivity for SERT (and not DAT or NET) is associated with an absence of cardiovascular side effects. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2012.03.042
• 作为产物：
  描述：

  1-(benzo[d]thiazol-2-yl)-4-hydroxybutan-1-one 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 12.58h， 以43%的产率得到1-(benzo[d]thiazol-2-yl)-4-iodobutan-1-one
  参考文献：
  名称：

  Benzothiazoles as probes for the 5HT1A receptor and the serotonin transporter (SERT): A search for new dual-acting agents as potential antidepressants

  摘要：

  The synthesis and evaluation of several benzothiazole-based compounds are described in an attempt to identify novel dual-acting 5HT(1A) receptor and SERT inhibitors as new antidepressants. Binding affinities at the 5HT(1A) receptor and the serotonin transporter do not appear to be congruent and other areas of the binding sites would need to be explored in order to improve binding simultaneously at both sites. Compounds 20 and 23 show moderate binding affinity at the 5HT(1A) receptor and the SERT site and thus, have the potential to be further explored as dual-acting agents. In addition, compound 20 binds with low affinity to the dopamine transporter (DAT), the norepinephrine transporter (NET) and 5HT(2C) receptor, which are desirable properties as selectivity for SERT (and not DAT or NET) is associated with an absence of cardiovascular side effects. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2012.03.042

文献信息

• Structure–activity relationship studies of SYA 013, a homopiperazine analog of haloperidol
  作者：Kwakye Peprah、Xue Y. Zhu、Suresh V.K. Eyunni、Jagan R. Etukala、Vincent Setola、Bryan L. Roth、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2012.01.022

  日期：2012.3

  Structure-activity relationship studies on 4-(4-(4-chlorophenyl)-1,4-diazepan-1-yl)-1-(4-fluorophenyl) butan-1-one (SYA 013), a homopiperazine analog of haloperidol has resulted in an understanding of the effect of structural modifications on binding affinity at dopamine and serotonin receptor subtypes. Further exploration, using bioisosteric replacement strategies has led to the identification of several new agents including compounds 7, 8, 11 and 12 which satisfy the initial criteria for further exploration as new antipsychotic agents. In addition, compound 18, a D-3 selective tropanol, has been identified as having the potential for further optimization into a useful drug which may combat neuropsychiatric diseases. Published by Elsevier Ltd.
• Benzothiazoles as probes for the 5HT1A receptor and the serotonin transporter (SERT): A search for new dual-acting agents as potential antidepressants
  作者：Xue Y. Zhu、Jagan R. Etukala、Suresh V.K. Eyunni、Vincent Setola、Bryan L. Roth、Seth Y. Ablordeppey

  DOI：10.1016/j.ejmech.2012.03.042

  日期：2012.7

  The synthesis and evaluation of several benzothiazole-based compounds are described in an attempt to identify novel dual-acting 5HT(1A) receptor and SERT inhibitors as new antidepressants. Binding affinities at the 5HT(1A) receptor and the serotonin transporter do not appear to be congruent and other areas of the binding sites would need to be explored in order to improve binding simultaneously at both sites. Compounds 20 and 23 show moderate binding affinity at the 5HT(1A) receptor and the SERT site and thus, have the potential to be further explored as dual-acting agents. In addition, compound 20 binds with low affinity to the dopamine transporter (DAT), the norepinephrine transporter (NET) and 5HT(2C) receptor, which are desirable properties as selectivity for SERT (and not DAT or NET) is associated with an absence of cardiovascular side effects. Published by Elsevier Masson SAS.