1-(3-氨基丙基)-4-羟基-4-苯基哌啶 | 5193-58-8

• 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: 1-(3-氨基丙基)-4-羟基-4-苯基哌啶
• 英文名称: 1-(3-aminopropyl)-4-hydroxy-4-phenylpiperidine
• 英文别名: (3-aminopropyl)-4-hydroxy-4-phenylpiperidine；3-[4-Hydroxy-4-phenyl-piperidin-1-yl]-propylamine；1-(3-aminopropyl)-4-phenylpiperidin-4-ol
• CAS: 5193-58-8
• 化学式: C₁₄H₂₂N₂O
• 分子量: 234.341
• InChiKey: RNIZKQNVMRVHBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-氨基丙基)-4-羟基-4-苯基哌啶 生成 3-(3,4-Difluoro-phenyl)-5-oxo-morpholine-4-carboxylic acid-{3-[4-hydroxy-4-phenyl-piperidin-1-yl]-propyl}amide
  参考文献：
  名称：

  Morpholinone and morpholine derivatives and uses thereof

  摘要：

  该发明涉及对吗啡酮和吗啡啶衍生物的选择性拮抗剂，这些衍生物对人类α1a受体具有选择性。该发明还涉及这些化合物的用途，用于降低眼压、抑制胆固醇合成、松弛下尿道组织、治疗良性前列腺增生、阳痿、心律失常、交感介导的疼痛、偏头痛，以及用于治疗任何需要α1a受体拮抗作用的疾病。该发明还提供了一种药物组合物，包括上述定义的化合物的治疗有效量和药用可接受载体。

  公开号：

  US06218390B1
• 作为产物：
  描述：

  3-(4-hydroxy-4-phenylpiperidin-1-yl)propionitrile 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 以3.12 g (83%)的产率得到1-(3-氨基丙基)-4-羟基-4-苯基哌啶
  参考文献：
  名称：

  Dihydropyridines and new uses thereof

  摘要：

  该发明提供了一种治疗良性前列腺增生的方法，包括向受试者施用具有以下结构的化合物的治疗有效量： 其中Y为--(CH.sub.2).sub.n --，其中n为1、2、3、4或5；--(CH.sub.2).sub.h --O--(CH.sub.2).sub.k --，其中h和k独立且相同或不同，为2、3或4；--(CH.sub.2).sub.h --CH.dbd.CH--(CH.sub.2).sub.k --；或--(CH.sub.2).sub.h --C.tbd.C--(CH.sub.2).sub.k --，其中h和k独立且相同或不同，为1、2、3或4；其中Z为O、NH或CH.sub.2；其中R.sup.1为线性或支链烷基、烷氧基烷基或芳基烷基；其中R.sup.2和R.sup.4独立且相同或不同，为H，或线性或支链烷基；其中R.sup.3为H、线性或支链烷基、烷氧基、烷氧基烷基或酰基；其中R.sup.5和R.sup.6独立且相同或不同，为H、OH、Cl、Br、F、NO.sub.2、CN、CF.sub.3或NH.sub.2，或线性或支链烷基、烷氧基、烷氧羰基、酰基、烷基亚砜、烷基砜、或单烷基或二烷基氨基基团。还公开了含有一、两个或三个环的其他活性化合物，以及由此制备的药物组合物和在治疗BPH、抑制胆固醇合成和降低眼压中的使用方法。

  公开号：

  US05767131A1

文献信息

• A Structure−Activity Relationship Study of Novel Phenylacetamides Which Are Sodium Channel Blockers
  作者：Ioannis Roufos、Sheryl Hays、Roy D. Schwarz

  DOI：10.1021/jm950467y

  日期：1996.1.1

  A structure-activity relationship study of a series of novel Na+ channel blockers, structurally related to N-[3-(2,6-dimethyl-1-piperidinyl)propyl]-alpha-phenylbenzeneacetamide (1, PD85639) is described. The diphenylacetic acid portion of the molecule was left unchanged throughout the study, while structural features in the amine portion and the amide alkyl linkage of the molecule were modified. The compounds were tested for inhibition of veratridine-stimulated Na+ influx in CHO cells expressing type IIA Na+ channels. Several derivatives show a trend toward more potent Na+ channel blockade activity with increasing lipophilicity of the amine portion of the molecule. The presence of a phenyl ring near the amine increases inhibitory potency. A three-carbon spacer between the amide and amine is optimal, and a secondary amide linkage is preferred.
• Design and Synthesis of Novel α_1a Adrenoceptor-Selective Dihydropyridine Antagonists for the Treatment of Benign Prostatic Hyperplasia
  作者：Dhanapalan Nagarathnam、John M. Wetzel、Shou Wu Miao、Mohammad R. Marzabadi、George Chiu、Wai C. Wong、Xingfang Hong、James Fang、Carlos Forray、Theresa A. Branchek、William E. Heydorn、Raymond S. L. Chang、Theodore Broten、Terry W. Schorn、Charles Gluchowski

  DOI：10.1021/jm980506g

  日期：1998.12.1

  We report the synthesis and evaluation of novel alpha(1a) adrenoceptor subtype-selective antagonists. Systematic modification of the lipophilic 4,4-diphenylpiperidinyl moiety of the dihydropyridine derivatives 1 and 2 provided several highly selective and potent alpha(1a), antagonists. From this series, we identified the 4-(methoxycarbonyl)-4-phenylpiperidine analogue SNAP 5540 (-) [(-)-63] for further characterization. When examined in an isolated human prostate tissue assay, this compound was found to have a K-i of 2.8 nM, in agreement with the cloned human receptor binding data (K-i = 2.42 nM). Further evaluation of the compound in isolated dog prostate tissue showed a K-i of 3.6 nM and confirmed it to be a potent antagonist (K-b = 1.6 nM). In vivo, this compound effectively blocked the phenylephrine-stimulated increase in intraurethral pressure (IUP) in mongrel dogs, at doses which did not significantly affect the arterial pressure (diastolic blood pressure, DBP), with a DBP K-b/IUP K-b ratio of 16. In addition, (-)-63 also showed greater than 40 000-fold selectivity over the rat L-type calcium channel and 200-fold selectivity over several G protein-coupled receptors, including histamine and serotonin subtypes. These findings prove that alpha(1a) adrenoceptor-subtype selective antagonists such as (-)-63 may be developed as uroselective agents for an improved treatment of BPH over nonselective alpha(1) antagonists such as prazosin and terazosin, with fewer side effects.
• Diurno; Mazzoni; Capasso, Il Farmaco, 1997, vol. 52, # 4, p. 237 - 241
  作者：Diurno、Mazzoni、Capasso、Izzo、Bolognese

  DOI：——

  日期：——
• MORPHOLINONE AND MORPHOLINE DERIVATIVES AND USES THEREOF
  申请人：SYNAPTIC PHARMACEUTICAL CORPORATION

  公开号：EP1140876A1

  公开（公告）日：2001-10-10
• US4006232A
  申请人：——

  公开号：US4006232A

  公开（公告）日：1977-02-01