3-(5-bromopentyl)benzo[d]thiazol-2(3H)-one | 1016539-19-7

• 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: 3-(5-bromopentyl)benzo[d]thiazol-2(3H)-one
• 英文别名: 3-(5-Bromopentyl)-1,3-benzothiazol-2-one
• CAS: 1016539-19-7
• 化学式: C₁₂H₁₄BrNOS
• 分子量: 300.219
• InChiKey: MMYLQRHQTPPEOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  环己亚胺 、 3-(5-bromopentyl)benzo[d]thiazol-2(3H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以72%的产率得到3-(5-(azepan-1-yl)pentyl)benzo[d]thiazol-2(3H)-one
  参考文献：
  名称：

  苯并[d]噻唑-2(3H)酮基σ受体配体的构效关系研究

  摘要：

  在此，我们报告SAR研究，其中涉及基于苯并[ d ]噻唑-2( 3H )酮的σ受体(σ)配体的接头长度、芳基取代和烷基胺环大小的结构修饰。该系列中的许多化合物对 σ 受体亚型表现出低纳摩尔亲和力。特别是， 8a对 σ-1 受体表现出高亲和力（σ-1 K i = 4.5 nM），并对 σ-2 受体表现出中等高的选择性（483 倍）。

  DOI：

  10.1016/j.bmcl.2013.06.032
• 作为产物：
  描述：

  2-羟基苯并噻唑 、 1,5-二溴戊烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 3-(5-bromopentyl)benzo[d]thiazol-2(3H)-one
  参考文献：
  名称：

  新型芳基哌嗪基烷基2-苯并恶唑酮和2-苯并噻唑酮作为5-HT 7和5-HT 1A受体配体的结构-活性关系和分子建模研究

  摘要：

  一种新型系列arylpiperazinylalkyl 2- benzoxazolones和2- benzothiazolones的18 - 38被设计，合成和测试，以评估其对5-HT亲和力7和5-HT 1A受体。具有2-苯并噻唑酮核的化合物通常具有比相应的2-苯并恶唑酮化合物更高的亲和力值。特别地，在2-苯并噻唑酮和芳基哌嗪之间具有六或七个碳链接头的衍生物的K i值在5-HT 1A受体的亚纳摩尔范围内，而在5-HT 7的纳摩尔范围低。受体，表明它们可能是有趣的双重配体。分子建模研究表明，在5-HT 1A和5-HT 7受体的同源性模型中，所研究化合物的对接姿势不同，这说明了它们在实验上确定的亲和力和普遍的低选择性。此外，结构相互作用指纹分析确定了两个5-羟色胺受体结合口袋内长链芳基哌嗪的特异性相互作用的重要氨基酸残基。

  DOI：

  10.1016/j.ejmech.2014.08.023

文献信息

• Conversion of a Highly Selective Sigma-1 Receptor–Ligand to Sigma-2 Receptor Preferring Ligands with Anticocaine Activity
  作者：Christophe Mésangeau、Sanju Narayanan、Andrea M. Green、Jamaluddin Shaikh、Nidhi Kaushal、Eddy Viard、Yan-Tong Xu、James A. Fishback、Jacques H. Poupaert、Rae R. Matsumoto、Christopher R. McCurdy

  DOI：10.1021/jm701357m

  日期：2008.3.13

  Cocaine's toxicity can be mitigated by blocking its interaction with sigma-1 receptors. The involvement of sigma-2 receptors remains unclear. To investigate their potential role, we have designed compounds through a convergent synthesis utilizing a highly selective sigma-1 ligand and elements of a selective sigma-2 ligand. Among the synthesized compounds was produced a subnanomolar sigma-2 ligand with an 11-fold preference over sigma-1 receptors. These compounds may be useful in developing effective pharmacotherapies for cocaine toxicity.
• Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents
  作者：Ahmed H. Abdelazeem、Shabana I. Khan、Stephen W. White、Kenneth J. Sufka、Christopher R. McCurdy

  DOI：10.1016/j.bmc.2015.04.057

  日期：2015.7

  Benzoxazolone and benzothiazolone were used as template blocks to develop two series of dimers as anti-inflammatory and analgesic agents based on the concept of bivalent ligands. The first series (I) involved varying the carbon chain lengths extending from the piperazine core to the nitrogen atom of the dibenzo[d]oxazol-2(3H)-one or dibenzo[d]thiazol-2(3H)-one. The second series (II) was designed by changing the attachment point. All compounds were screened for their in vitro anti-inflammatory activity in terms of the inhibition of inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-kappa B). Seventeen compounds inhibited both targets. Eleven of them exhibited IC50 values below 3 mu M while five compounds showed IC50 values of 1 mu M or below. Most of the compounds were found to be devoid of cytotoxicity against mammalian kidney and solid tumors cell lines up to 25 mu g/mL. In vivo anti-inflammatory and antinociceptive studies revealed that compounds 3j, 5t and 8b have significant anti-inflammatory and analgesic activity comparable to that of indomethacin and ketorolac, respectively. (C) 2015 Elsevier Ltd. All rights reserved.