3-(4-bromobutyl)benzo[d]thiazol-2(3H)-one | 1016539-17-5

• 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-(4-bromobutyl)benzo[d]thiazol-2(3H)-one
• 英文别名: 3-(4-Bromobutyl)-1,3-benzothiazol-2-one
• CAS: 1016539-17-5
• 化学式: C₁₁H₁₂BrNOS
• 分子量: 286.192
• InChiKey: YOKQZMKPTFHARP-UHFFFAOYSA-N

物化性质

• 沸点：
  404.7±47.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  3-(4-bromobutyl)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 2.5h， 生成 3-(6-(4-(4-(2-oxobenzo[d]thiazol-3(2H)-yl)butyl)piperazin-1-yl)hexyl)benzo[d]thiazol-2(3H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.04.057
• 作为产物：
  描述：

  2-氨基苯硫醇 在 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 7.0h， 生成 3-(4-bromobutyl)benzo[d]thiazol-2(3H)-one
  参考文献：
  名称：

  Biological Evaluation and Binding Mechanism of 5-HT7 Specific Arylpiperazinyl–Alkyl Benzothiazolone: Radiobiology and Photo-physical Studies

  摘要：

  DOI：

  10.1007/s10895-023-03266-4

文献信息

• Structure activity relationship study of benzo[d]thiazol-2(3H)one based σ receptor ligands
  作者：Rohit Bhat、James A. Fishback、Rae R. Matsumoto、Jacques H. Poupaert、Christopher R. McCurdy

  DOI：10.1016/j.bmcl.2013.06.032

  日期：2013.9

  Herein we report the SAR study which involved structural modifications to the linker length, aryl substitution and alkylamine ring size of the benzo[d]thiazol-2(3H)one based sigma receptor (σ) ligands. Many compounds in this series displayed low nanomolar affinity for the σ receptor subtypes. In particular, 8a showed high affinity (σ-1 Ki = 4.5 nM) for σ-1 receptors and moderately high selectivity

  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）。
• Structure–activity relationships and molecular modeling studies of novel arylpiperazinylalkyl 2-benzoxazolones and 2-benzothiazolones as 5-HT7 and 5-HT1A receptor ligands
  作者：Loredana Salerno、Valeria Pittalà、Maria N. Modica、Maria A. Siracusa、Sebastiano Intagliata、Alfredo Cagnotto、Mario Salmona、Rafał Kurczab、Andrzej J. Bojarski、Giuseppe Romeo

  DOI：10.1016/j.ejmech.2014.08.023

  日期：2014.10

  5-HT7 and 5-HT1A receptors. Compounds with a 2-benzothiazolone nucleus generally had affinity values higher than the corresponding 2-benzoxazolone compounds. In particular, derivatives possessing a six or seven carbon chain linker between 2-benzothiazolone and arylpiperazine had Ki values in the subnanomolar range for the 5-HT1A receptor and in the low nanomolar range for the 5-HT7 receptor, indicating

  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。
• 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.