tert-butyl 4-(2-hydroxypropyl)piperidine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl 4-(2-hydroxypropyl)piperidine-1-carboxylate
• 英文别名: 1-t-Butoxycarbonyl-4-(2-(RS)-hydroxypropyl)piperidine
• 化学式: C₁₃H₂₅NO₃
• 分子量: 243.346
• InChiKey: AHKWWVWQZVBPAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-hydroxypropyl)piperidine-1-carboxylate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 4-(2-hydroxypropyl)piperidine hydrochloride
  参考文献：
  名称：

  Discovery of 2-methyl-1-{1-[(5-methyl-1H-indol-2-yl)carbonyl]piperidin-4-yl}propan-2-ol: A novel, potent and selective type 5 17β-hydroxysteroid dehydrogenase inhibitor

  摘要：

  Type 5 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD5), also known as aldo-keto reductase 1C3 (AKR1C3), is a member of the aldo-keto reductase superfamily of enzymes and is expressed in the human prostate. One of the main functions of 17 beta-HSD5 is to catalyze the conversion of the weak androgen, androstenedione, to the potent androgen, testosterone. The concentration of intraprostatic 5 alpha-dihydrotestosterone (DHT) in patients following chemical or surgical castration has been reported to remain as high as 39% of that of healthy men, with 17 beta-HSD5 shown to be involved in this androgen synthesis. Inhibition of 17 beta-HSD5 therefore represents a promising target for the treatment of castration-resistant prostate cancer (CRPC). To investigate this, we conducted high-throughput screening (FITS) and identified compound 2, which displayed a structure distinct from known 17 beta-HSD5 inhibitors. To optimize the inhibitory activity of compound 2, we first introduced a primary alcohol group. We then converted the primary alcohol group to a tertiary alcohol, which further enhanced the inhibitory activity, improved metabolic stability, and led to the identification of compound 17. Oral administration of compound 17 to castrated nude mice bearing the CWR22R xenograft resulted in the suppression of androstenedione (AD)-induced intratumoral testosterone production. Compound 17 also demonstrated good isoform selectivity, minimal inhibitory activity against either CYP or hERG, and enhanced pharmacokinetic and physicochemical properties. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.025
• 作为产物：
  描述：

  甲基溴化镁 、 4-(2-氧代乙基)哌啶-1-羧酸叔丁酯 在 水 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 生成 tert-butyl 4-(2-hydroxypropyl)piperidine-1-carboxylate
  参考文献：
  名称：

  PIPERIDINE DERIVATIVE

  摘要：

  公开号：

  EP2181990B1

文献信息

• [EN] COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE TROUBLES MÉTABOLIQUES
  申请人：PROSIDION LTD

  公开号：WO2010103334A1

  公开（公告）日：2010-09-16

  The present invention is directed to therapeutic compounds of the following formula (I) which have activity as agonists of GPR119 and are useful for the treatment of metabolic disorders including type II diabetes.

  本发明涉及具有以下式（I）的治疗化合物，其作为GPR119的激动剂具有活性，并可用于治疗包括2型糖尿病在内的代谢紊乱。
• 4-alkyl piperidinyl pyrrolidine modulators of chemokine receptor activity
  申请人：——

  公开号：US20020013348A1

  公开（公告）日：2002-01-31

  The present invention is directed to pyrrolidine compounds of the formula I: 1 (wherein R 1 , R 2 , R 3 , R 4c , R 4d , and R 4f are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-3 and/or CCR-5.

  本发明涉及公式I:1中的吡咯烷化合物（其中R1、R2、R3、R4c、R4d和R4f在此处定义），这些化合物可用作化学因子受体活性的调节剂。具体来说，这些化合物可用作化学因子受体CCR-3和/或CCR-5的调节剂。
• Piperidine derivative
  申请人：Kakefuda Akio

  公开号：US08513422B2

  公开（公告）日：2013-08-20

  As a result of studies on compounds having a selective inhibitory activity against 17βHSD type 5, the present inventors have confirmed that a 1-[(indol-2-yl)carbonyl]piperidyl}alkanol derivative has a potent selective inhibitory activity against 17βHSD type 5. The invention has been completed based on these findings. The compound of the present invention can be used as an agent for treating and/or an agent for preventing diseases associated with 17βHSD type 5, such as benign prostatic hyperplasia and prostate cancer, without accompanying adverse effects due to a decrease in testosterone.

  通过对具有选择性抑制17βHSD型5活性的化合物的研究，本发明人已经确认一种1-[(indol-2-yl)carbonyl]piperidyl}alkanol衍生物具有强大的选择性抑制17βHSD型5的活性。本发明基于这些发现已经完成。本发明的化合物可用作治疗和/或预防与17βHSD型5相关的疾病的药物，如良性前列腺增生和前列腺癌，而不伴随着由于睾酮降低而引起的不良反应。
• COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS
  申请人：Prosidion Limited

  公开号：EP2406251A1

  公开（公告）日：2012-01-18
• FURIN INHIBITORS
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP3790871A1

  公开（公告）日：2021-03-17