2-(2-chloroethylamino)-5,6-dihydro-1,3-benzothiazol-7(4H)-one | 1352816-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-chloroethylamino)-5,6-dihydro-1,3-benzothiazol-7(4H)-one
• CAS: 1352816-77-3
• 化学式: C₉H₁₁ClN₂OS
• 分子量: 230.718
• InChiKey: BBXSDDJLRAKNAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,3-二甲基哌啶 、 2-(2-chloroethylamino)-5,6-dihydro-1,3-benzothiazol-7(4H)-one 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-(3,3-dimethylpiperidin-1-yl)-1-{[7(4H)-oxo-5,6-dihydro-1,3-benzothiazol-2-yl]amino}ethane
  参考文献：
  名称：

  Synthesis and binding assays of novel 3,3-dimethylpiperidine derivatives with various lipophilicities as σ1 receptor ligands

  摘要：

  Starting from two carbocyclic analogs, a series of 3,3-dimethylpiperidine derivatives was prepared and tested in radioligand binding assays at sigma(1) and sigma(2) receptors, and at Delta(8)-Delta(7) sterol isomerase (SI) site. The novel compounds mostly bear heterocyclic rings or bicyclic nucleus of differing lipophilicities. Compounds 18a and 19a,b demonstrated the highest sigma(1) affinity (K-i = 0.14-0.38 nM) with a good selectivity versus sigma(2) binding. Among them, 18a had the lowest C log D value (3.01) and only 19b was selective versus SI too. Generally, it was observed that more planar and hydrophilic heteronuclei conferred a decrease in affinity for both sigma receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.023
• 作为产物：
  描述：

  2-chloro-N-[7(4H)-oxo-5,6-dihydro-1,3-benzothiazol-2-yl]acetamide 在 dimethyl sulfide borane 、 三氟化硼乙醚 、 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.0h， 以30%的产率得到2-(2-chloroethylamino)-5,6-dihydro-1,3-benzothiazol-7(4H)-one
  参考文献：
  名称：

  Synthesis and binding assays of novel 3,3-dimethylpiperidine derivatives with various lipophilicities as σ1 receptor ligands

  摘要：

  Starting from two carbocyclic analogs, a series of 3,3-dimethylpiperidine derivatives was prepared and tested in radioligand binding assays at sigma(1) and sigma(2) receptors, and at Delta(8)-Delta(7) sterol isomerase (SI) site. The novel compounds mostly bear heterocyclic rings or bicyclic nucleus of differing lipophilicities. Compounds 18a and 19a,b demonstrated the highest sigma(1) affinity (K-i = 0.14-0.38 nM) with a good selectivity versus sigma(2) binding. Among them, 18a had the lowest C log D value (3.01) and only 19b was selective versus SI too. Generally, it was observed that more planar and hydrophilic heteronuclei conferred a decrease in affinity for both sigma receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.023