3-methyl-6-(4-hydroxybutyryl)benzothiazolinone | 183198-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-6-(4-hydroxybutyryl)benzothiazolinone
• 英文别名: 6-(4-Hydroxybutanoyl)-3-methyl-1,3-benzothiazol-2-one
• CAS: 183198-05-2
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: JRWBZGKQQJBPOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-6-(4-hydroxybutyryl)benzothiazolinone 在 吡啶 、 甲醇 、 三乙基硅烷 、 氢溴酸 、 potassium carbonate 、 一水合肼 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 54.0h， 生成 8-(4-{Methyl-[4-(3-methyl-2-oxo-2,3-dihydro-benzothiazol-6-yl)-butyl]-amino}-butyl)-8-aza-spiro[4.5]decane-7,9-dione
  参考文献：
  名称：

  Diouf, Ousmane; Depreux, Patrick; Lesieur, Daniel, Heterocycles, 1995, vol. 41, # 6, p. 1219 - 1234

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基苯并噻唑 在 sodium hydroxide 、 PPA 作用下， 反应 5.0h， 生成 3-methyl-6-(4-hydroxybutyryl)benzothiazolinone
  参考文献：
  名称：

  Synthesis and evaluation of new 2-piperazinylbenzothiazoles with high 5-HT1A and 5-HT3 affinities

  摘要：

  Original 2-piperazinylbenzothiazole derivatives were synthesized and studied as mixed ligands for serotoninergic 5-HT1A and 5-HT3 receptors. The studied compounds exhibited significant affinities for these two serotoninergic receptor subtypes. The pharmacological profile of these ligands was agonist for 5-HT1A receptors and antagonist for 5-HT3 receptor subsites. Compounds with such a pharmacological profile are of clinical relevance in the treatment of psychotropic diseases (eg, anxiety, depression and schizophrenia). The present paper reports the chemistry and the in vitro pharmacological evaluation of these ligands.

  DOI：

  10.1016/0223-5234(96)88289-4

文献信息

• New substituted benzothiazolinones
  申请人：Adir et Compagnie

  公开号：US05084469A1

  公开（公告）日：1992-01-28

  Compounds of general formula (I): ##STR1## in which: R.sub.1 represents a hydrogen atom or a lower alkyl group, and R.sub.2 represents a substituted or unsubstituted alkyl, a phenyl or a substituted or unsubstituted heteroaryl, their enantiomers, diastereoisomers and epimers and their addition salts with a pharmaceutically acceptable base when R.sub.1 represents a hydrogen atom or when R.sub.2 comprises a carboxylic acid group. Medicinal products.

  通式（I）的化合物：##STR1## 其中：R.sub.1代表氢原子或较低的烷基基团，R.sub.2代表取代或未取代的烷基、苯基或取代或未取代的杂环基，它们的对映异构体、顺反异构体和外消旋体以及它们与药用可接受碱的加合物，当R.sub.1代表氢原子或R.sub.2包括羧酸基团时。药物产品。
• Synthesis and pharmacological evaluation of 6-piperidino- and 6-piperazinoalkyl-2(3 H )-benzothiazolones as mixed σ/5-HT 1A ligands
  作者：Ange Mouithys-Mickalad、Jacques H. Poupaert、Santi Spampinato、Daniel Lesieur

  DOI：10.1016/s0960-894x(02)00123-3

  日期：2002.4

  In an effort to produce new pharmacological probes with mixed sigma/5-HT1A affinity, we have synthesized a series of 12 original 6-piperidino- or piperazino-alkyl-2(3H)-benzothiazolones and their receptor binding profile (sigma, 5-HT1A, 5-HT2A, 5-HT3, D-2, H-1, and M-1) was determined. The best mixed sigma/5-HT1A affinity profile was found within the piperidine series with 4-benzyl substitution associated to linker methylene chain n = 2 (K-i 5 and 4 nM, respectively). Moreover, a highly selective sigma2 ligand was obtained with a 3,4-dichlorobenzyl substitution associated to n = 4 (K-i 2 nM, selectivity ratio sigma1/sigma2 = 70). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Poupaert, Jacques H.; Kanyonyo, Martial; Ucar, Huseyin, Bulletin des Societes Chimiques Belges, 1996, vol. 105, # 7, p. 397 - 402
  作者：Poupaert, Jacques H.、Kanyonyo, Martial、Ucar, Huseyin、Mouithys, Ange M.、Diouf, Ousman、Lesieur, Daniel

  DOI：——

  日期：——
• US5084469A
  申请人：——

  公开号：US5084469A

  公开（公告）日：1992-01-28
• US5162350A
  申请人：——

  公开号：US5162350A

  公开（公告）日：1992-11-10