4-(2-羟乙基)哌啶-1-苯甲醛 | 141047-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(2-羟乙基)哌啶-1-苯甲醛
• 英文名称: N-formyl-4-(2-hydroxyethyl)piperidine
• 英文别名: 4-(2-hydroxyethyl)piperidine-1-carbaldehyde
• CAS: 141047-47-4
• 化学式: C₈H₁₅NO₂
• mdl: MFCD06637672
• 分子量: 157.213
• InChiKey: DANYAIYXZFDQGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-(2-羟乙基)哌啶-1-苯甲醛 在 氢氧化钾 、 sodium hydride 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 为溶剂， 反应 45.75h， 生成 (S)-2-{(S)-1-Benzyl-2-[4-(2-methoxy-ethyl)-piperidin-1-yl]-2-oxo-ethoxy}-hexanoic acid
  参考文献：
  名称：

  Nonpeptide renin inhibitors employing a novel 3-aza (or oxa)-2,4-dialkyl glutaric acid moiety as a P2/P3 amide bond replacement

  摘要：

  A new series of renin inhibitors has been developed. The inhibitors feature a novel replacement for the P2/P3 dipeptide moiety normally associated with renin inhibitors. The dipeptide replacement was a (2S,4S)-3-aza(or oxa)-2,4-di-alkylglutaric acid amide. Extensive structure-activity relationship studies determined that optimum potency was achieved when inhibitors employed a benzyl and butyl group at the C(4) and C(2) carbon position, respectively. In addition, maximum in vitro potency was obtained when the N-terminus was functionalized by incorporating a 4-(1,3-dioxabutyl)piperidine amide. SAR data suggested that the 1,3-dioxabutyl group (methoxymethyl ether) interacted by hydrogen bonding to groups in the S4 domain of renin. This hypothesis was strengthened when a 4-butylpiperidine amide was substituted and inhibitor potency decreased dramatically. Inhibitors employing this novel dipeptide mimic were prepared by coupling the glutaric acid amides with either the transition-state mimic (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (18) or the hydroxyethylene dipeptide isostere. The glutaric acid amides were prepared by two general procedures. The first procedure involved the reductive amination of alpha-amino acid esters with alpha-keto esters. The second procedure involved the displacement reaction of alpha-bromo esters or acids with alpha-amino acid amides.

  DOI：

  10.1021/jm00088a006
• 作为产物：
  描述：

  4-哌啶乙醇 、 甲酸甲酯 反应 1.0h， 以95%的产率得到4-(2-羟乙基)哌啶-1-苯甲醛
  参考文献：
  名称：

  Nonpeptide renin inhibitors employing a novel 3-aza (or oxa)-2,4-dialkyl glutaric acid moiety as a P2/P3 amide bond replacement

  摘要：

  A new series of renin inhibitors has been developed. The inhibitors feature a novel replacement for the P2/P3 dipeptide moiety normally associated with renin inhibitors. The dipeptide replacement was a (2S,4S)-3-aza(or oxa)-2,4-di-alkylglutaric acid amide. Extensive structure-activity relationship studies determined that optimum potency was achieved when inhibitors employed a benzyl and butyl group at the C(4) and C(2) carbon position, respectively. In addition, maximum in vitro potency was obtained when the N-terminus was functionalized by incorporating a 4-(1,3-dioxabutyl)piperidine amide. SAR data suggested that the 1,3-dioxabutyl group (methoxymethyl ether) interacted by hydrogen bonding to groups in the S4 domain of renin. This hypothesis was strengthened when a 4-butylpiperidine amide was substituted and inhibitor potency decreased dramatically. Inhibitors employing this novel dipeptide mimic were prepared by coupling the glutaric acid amides with either the transition-state mimic (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (18) or the hydroxyethylene dipeptide isostere. The glutaric acid amides were prepared by two general procedures. The first procedure involved the reductive amination of alpha-amino acid esters with alpha-keto esters. The second procedure involved the displacement reaction of alpha-bromo esters or acids with alpha-amino acid amides.

  DOI：

  10.1021/jm00088a006

文献信息

• [EN] THERAPEUTIC COMPOUNDS AND THEIR USE IN TREATING DISEASES AND DISORDERS<br/>[FR] COMPOSÉS THÉRAPEUTIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES ET DE TROUBLES
  申请人：MYRIAD GENETICS INC

  公开号：WO2009065035A1

  公开（公告）日：2009-05-22

  The invention provides novel therapeutic compounds, pharmaceutical compositions comprising these compounds, and methods for using these compounds and compositions to treat diseases and disorders, such as cancer.

  这项发明提供了新型治疗化合物，包括这些化合物的药物组合物，以及使用这些化合物和组合物治疗疾病和疾病的方法，如癌症。
• Indium-Catalyzed N-Formylation of Amines under Solvent-Free Conditions
  作者：Doo Jang、Joong-Gon Kim

  DOI：10.1055/s-0029-1219784

  日期：2010.5

  We have developed a simple, mild method for N-formylation of a wide variety of amines in the presence of indium metal as a catalyst under solvent-free conditions. This reaction is applicable to the chemoselective N-formylation of amino groups and α-amino acid esters without epimerization.

  我们开发了一种简单温和的方法，在无溶剂条件下，以金属铟为催化剂，对多种胺进行 N-甲酰化反应。该反应适用于氨基和 δ- 氨基酸酯的化学选择性 N-甲酰化反应，且不会发生表聚反应。
• Carbazole derivatives and their use as neuropeptide y5 receptor ligands
  申请人：——

  公开号：US20040067999A1

  公开（公告）日：2004-04-08

  Compounds of formula (I): are described wherein R 1 -R 6 and m are as defined within. Processes for their preparation and their use as NPY 5 inhibitors is described.

  描述了化学式（I）的化合物，其中R1-R6和m的定义如所述。描述了它们的制备过程以及它们作为NPY 5抑制剂的用途。
• Substituted indole ligands for the ORL-1 receptor
  申请人：Ronzoni Silvano

  公开号：US20090275555A1

  公开（公告）日：2009-11-05

  New ligands for the ORL-1 receptor are described, useful for antagonising the activity of said receptors in a patient in need thereof, and for preventing and treating illnesses dependent on the activation of this receptor. The new compounds conform to structural formula (I) wherein R1, R2, R3, R4 are further defined in the description.

  本文描述了ORL-1受体的新配体，可用于拮抗需要该受体活性的患者，并用于预防和治疗依赖于该受体激活的疾病。新化合物符合结构式（I），其中R1，R2，R3，R4在描述中进一步定义。
• Therapeutic Compounds and Their Use in Treating Diseases and Disorders
  申请人：Bajji Ashok C.

  公开号：US20100292255A1

  公开（公告）日：2010-11-18

  The invention provides novel therapeutic compounds, pharmaceutical compositions comprising these compounds, and methods for using these compounds and compositions to treat diseases and disorders, such as cancer.

  该发明提供了新型治疗化合物、包含这些化合物的药物组合物以及使用这些化合物和组合物治疗疾病和疾病的方法，例如癌症。