O-(p-toluenesulfonyl)-3-(4-fluorophenoxy)propanol | 223136-61-6

• 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: O-(p-toluenesulfonyl)-3-(4-fluorophenoxy)propanol
• 英文别名: 3-(4-fluorophenoxy)propyl 4-methylbenzenesulfonate
• CAS: 223136-61-6
• 化学式: C₁₆H₁₇FO₄S
• 分子量: 324.373
• InChiKey: LKZHUQWQCURSMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-(p-toluenesulfonyl)-3-(4-fluorophenoxy)propanol 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 N-(1-(3-(4-fluorophenoxy)propyl)piperidin-4-yl)-2-oxobenzimidazole-1-carboxamide
  参考文献：
  名称：

  5-HT.sub.4 agonists and antagonists

  摘要：

  化合物的化学式为I：##STR1## 被用作5-HT.sub.4受体的拮抗剂和部分激动剂，并提供了治疗由5-HT.sub.4受体功能失调引起或受其影响的疾病的治疗方法。

  公开号：

  US06069152A1
• 作为产物：
  描述：

  3-(4-氟苯氧基)丙酸 在 硼烷 作用下， 以 四氢呋喃 、 吡啶 、 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 、 水 为溶剂， 生成 O-(p-toluenesulfonyl)-3-(4-fluorophenoxy)propanol
  参考文献：
  名称：

  5-HT.sub.4 agonists and antagonists

  摘要：

  化合物的化学式为I：##STR1## 被用作5-HT.sub.4受体的拮抗剂和部分激动剂，并提供了治疗由5-HT.sub.4受体功能失调引起或受其影响的疾病的治疗方法。

  公开号：

  US06069152A1

文献信息

• Synthesis and Structure−Activity Relationships of Potent and Orally Active 5-HT₄ Receptor Antagonists:  Indazole and Benzimidazolone Derivatives
  作者：John M. Schaus、Dennis C. Thompson、William E. Bloomquist、Alice D. Susemichel、David O. Calligaro、Marlene L. Cohen

  DOI：10.1021/jm970857f

  日期：1998.5.1

  aminoalkylene chain led to potent 5-HT4 receptor antagonists. In particular, those systems in which the basic amine was substituted with groups capable of forming hydrogen bonds showed increased 5-HT4 receptor antagonist activity. While some of these compounds displayed high affinity for other neurotransmitter receptors (in particular, 5-HT3, alpha1, and 5-HT2A receptors), as the conformational flexibility

  合成了一系列的吲哚-3-羧酰胺，吲唑-3-羧酰胺和苯并咪唑啉酮-3-羧酰胺，并评估了对大鼠食道中5-HT4受体的拮抗剂亲和力。与相应的吲哚类似物相比，吲唑和苯并咪唑酮系列中的3-内环戊胺衍生物具有更大的5-HT4受体亲和力。通过在芳香杂环的N-1烷基化进一步提高了5-HT4受体拮抗剂的亲和力。在一系列的1-异丙基吲唑-3-羧酰胺中，用单环哌啶环系统或无环氨基亚烷基链取代双环托烷环系统导致了有效的5-HT4受体拮抗剂。特别地，其中碱性胺被能够形成氢键的基团取代的那些系统显示出增加的5-HT 4受体拮抗剂活性。尽管这些化合物中的一些对其他神经递质受体（特别是5-HT3，α1和5-HT2A受体）表现出高亲和力，但随着胺部分构象柔韧性的提高，对5-HT4受体的选择性也提高了。从这一系列化合物中，我们确定了LY353433（1-（1-甲基乙基）-N- [2- [4-[（三环[3.3.1.1（3，7）]癸-1-基羰基）氨基]
• Process for preparing 3-substituted indazoles
  申请人：Eli Lilly and Company

  公开号：US05914405A1

  公开（公告）日：1999-06-22

  The invention provides a method of preparing compounds of formula I and VIII: ##STR1## which are useful intermediates to compounds that are used as antagonists and partial agonists for the serotonin receptor 5-HT.sub.4.

  本发明提供一种制备I和VIII式化合物的方法：##STR1## 这些化合物是有用的中间体，用于制备作为5-HT.sub.4受体拮抗剂和部分激动剂的化合物。
• 5-HT4 Agonists and antagonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0908459A1

  公开（公告）日：1999-04-14

  Compounds of formula I: are used as antagonists and partial agonists for the serotonin receptor 5-HT4 and provide therapeutic methods for treatment of disorders caused by or affected by dysfunction of the 5-HT4 receptor.

  式 I.化合物 用作血清素受体 5-HT4 的拮抗剂和部分激动剂，并为治疗由 5-HT4 受体功能障碍引起或受其影响的疾病提供治疗方法。
• Identification of a new selective dopamine D4 receptor ligand
  作者：Dinithia Sampson、Xue Y. Zhu、Suresh V.K. Eyunni、Jagan R. Etukala、Edward Ofori、Barbara Bricker、Nazarius S. Lamango、Vincent Setola、Bryan L. Roth、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2014.04.026

  日期：2014.6

  The dopamine D-4 receptor has been shown to play key roles in certain CNS pathologies including addiction to cigarette smoking. Thus, selective D-4 ligands may be useful in treating some of these conditions. Previous studies in our laboratory have indicated that the piperazine analog of haloperidol exhibits selective and increased affinity to the DAD(4) receptor subtype, in comparison to its piperidine analog. This led to further exploration of the piperazine moiety to identify new agents that are selective at the D-4 receptor. Compound 27 (KiD4 = 0.84 nM) was the most potent of the compounds tested. However, it only had moderate selectivity for the D-4 receptor. Compound 28 (KiD4 = 3.9 nM) while not as potent, was more discriminatory for the D-4 receptor subtype. In fact, compound 28 has little or no binding affinity to any of the other four DA receptor subtypes. In addition, of the 23 CNS receptors evaluated, only two, 5HT(1A)R and 5HT(2B)R, have binding affinity constants better than 100 nM (K-i < 100 nM). Compound 28 is a potentially useful D-4-selective ligand for probing disease treatments involving the D-4 receptor, such as assisting smoking cessation, reversing cognitive deficits in schizophrenia and treating erectile dysfunction. Thus, further optimization, functional characterization and evaluation in animal models may be warranted. Published by Elsevier Ltd.
• US05959121
  申请人：——

  公开号：——

  公开（公告）日：——