1-(benzo[d]thiazol-2-yl)-5-hydroxypentan-1-one | 85450-44-8

• 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)-5-hydroxypentan-1-one
• 英文别名: ZINC1609998；NSC607001；1-(1,3-Benzothiazol-2-yl)-5-hydroxypentan-1-one
• CAS: 85450-44-8
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: XMPHDJRROPBHNX-UHFFFAOYSA-N

物化性质

• 沸点：
  405.1±47.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(benzo[d]thiazol-2-yl)-5-hydroxypentan-1-one 在 咪唑 、 碘 、 potassium carbonate 、 三苯基膦 、 potassium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.58h， 生成 1-(benzo[d]thiazol-2-yl)-5-(4-phenylpiperazin-1-yl)pentan-1-one hydrochloride
  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：

  delta-戊内酯 、 苯并噻唑 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以99%的产率得到1-(benzo[d]thiazol-2-yl)-5-hydroxypentan-1-one
  参考文献：
  名称：

  2-锂硫代苯并噻唑对各种亲电试剂的一般反应性以及在α-羟基羰基化合物合成中作为甲酰基阴离子等价物的用途

  摘要：

  2-锂硫代苯并噻唑与各种亲电子试剂如醛、酮、羧酸酯、内酯、腈和酰胺的反应提供了预期的加成和取代产物。三甲基甲硅烷基氯很容易与苯并噻唑阴离子反应生成 2-三甲基甲硅烷基苯并噻唑，而常见的烷基卤化物，包括伯碘化物和苄基卤化物，以及环氧化物，不与阴离子反应。阴离子的这种特征亲核性也通过它与苯甲酰卤和 5-氯-2-戊酮的反应导致苯并噻唑基取代的小环醚的形成得到证实。为了证明 2-硫代苯并噻唑作为掩蔽甲酰基阴离子的价值，2-(α-羟基烷基)苯并噻唑在三个反应步骤中转化为α-羟基羰基化合物，而不会掩盖α-羟基。各种 2-(α-羟烷基)苯并噻唑与甲基碘在 DMF 中季铵化得到相应的 2-(α-羟烷基)-3-甲基苯...

  DOI：

  10.1246/bcsj.61.3637

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.
• Fluoride ion induced reactions of organocilanes with saturated lactones and αβ-enones
  作者：Alfredo Ricci、Mariella Fiorenza、M.Antonietta Grifagni、Giuseppe Bartolini、Giancarlo Seconi

  DOI：10.1016/s0040-4039(00)85577-x

  日期：1982.1
• RICCI, A.;FIORENZA, M.;GRIFAGNI, M. A.;BARTOLINI, G., TETRAHEDRON LETT., 1982, 23, N 48, 5079-5082
  作者：RICCI, A.、FIORENZA, M.、GRIFAGNI, M. A.、BARTOLINI, G.

  DOI：——

  日期：——
• General Reactivity of 2-Lithiobenzothiazole to Various Electrophiles and the Use as a Formyl Anion Equivalent in the Synthesis of α-Hydroxy Carbonyl Compounds
  作者：Hidenori Chikashita、Megumi Ishibaba、Keiji Ori、Kazuyoshi Itoh

  DOI：10.1246/bcsj.61.3637

  日期：1988.10

  demonstrated by its reaction with phenacyl halides and 5-chloro-2-pentanone leading to the formation of benzothiazolyl-substituted small-ring ethers. In order to demonstrate the value of 2-lithiobenzothiazole as a masked formyl anion, 2-(α-hydroxyalkyl)benzothiazoles were transformed into α-hydroxy carbonyl compounds in three reaction steps without masking the α-hydroxy groups. Quaternization of various

  2-锂硫代苯并噻唑与各种亲电子试剂如醛、酮、羧酸酯、内酯、腈和酰胺的反应提供了预期的加成和取代产物。三甲基甲硅烷基氯很容易与苯并噻唑阴离子反应生成 2-三甲基甲硅烷基苯并噻唑，而常见的烷基卤化物，包括伯碘化物和苄基卤化物，以及环氧化物，不与阴离子反应。阴离子的这种特征亲核性也通过它与苯甲酰卤和 5-氯-2-戊酮的反应导致苯并噻唑基取代的小环醚的形成得到证实。为了证明 2-硫代苯并噻唑作为掩蔽甲酰基阴离子的价值，2-(α-羟基烷基)苯并噻唑在三个反应步骤中转化为α-羟基羰基化合物，而不会掩盖α-羟基。各种 2-(α-羟烷基)苯并噻唑与甲基碘在 DMF 中季铵化得到相应的 2-(α-羟烷基)-3-甲基苯...
• 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.