Ethyl 4-hydroxypiperidine-2-carboxylate | 153710-85-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 4-hydroxypiperidine-2-carboxylate
• CAS: 153710-85-1
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: BJUUAHUCDQWKQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 4-hydroxypiperidine-2-carboxylate 在 palladium on activated charcoal 甲酸 、 4 A molecular sieve 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 25.0~80.0 ℃ 、413.69 kPa 条件下， 反应 12.0h， 生成 ethyl 4-(cyanomethyl)-N-methylpiperidine-2-carboxylate
  参考文献：
  名称：

  4-(Tetrazolylalkyl)piperidine-2-carboxylic acids. Potent and selective N-methyl-D-aspartic acid receptor antagonists with a short duration of action

  摘要：

  We have prepared a series of cis-4-(tetrazolylalkyl)piperidine-2-carboxylic acids as potent and selective N-methyl-D-aspartic acid (NMDA) receptor antagonists. NMDA antagonists may prove to be useful therapeutic agents, for instance, as anticonvulsants, in the treatment of neurodegenerative disorders such as Alzheimer's disease and in the prevention of neuronal damage that occurs during cerebral ischemia. The compounds prepared were evaluated in vitro in both receptor binding assays ([H-3]CGS-19755, [H-3]AMPA, and [H-3]kainic acid) and in a cortical-wedge preparation (versus NMDA, quisqualic acid, and kainic acid) to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. The most potent compound of this series, 15 (LY233053), selectively displaced [H-3]CGS-19755 binding with an IC50 of 107 +/- 7 nM and selectively antagonized responses due to NMDA in a cortical-wedge preparation with an IC50 of 4.2 +/- 0.4-mu-M. Compound 15 blocked both NMDA-induced convulsions in neonatal rats (minimum effective dose (MED) = 20 mg/kg ip) and NMDA-induced lethality in mice (MED = 5 mg/kg ip). This is the first example of an NMDA receptor antagonist that incorporates a tetrazole moiety as an omega-acid bioisostere. These amino acid antagonists are also unique from their phosphonic acid counterparts in that they have a shorter duration of action in vivo. For the treatment of acute disorders such as stroke, where an NMDA antagonist would be administered parenterally, the shorter duration of action may be beneficial, e.g., allowing for better dosage control. The combination of potent NMDA receptor antagonism and a short duration of action may make these compounds useful therapeutic agents in the treatment of a variety of neurological disorders.

  DOI：

  10.1021/jm00105a016
• 作为产物：
  描述：

  4-甲氧基吡啶-2-甲腈 在 Rh/Al₂O₃ 盐酸 、 氢溴酸 、 氢气 作用下， 以 乙醇 为溶剂， 100.0 ℃ 、6.89 MPa 条件下， 反应 82.0h， 生成 Ethyl 4-hydroxypiperidine-2-carboxylate
  参考文献：
  名称：

  4-(Tetrazolylalkyl)piperidine-2-carboxylic acids. Potent and selective N-methyl-D-aspartic acid receptor antagonists with a short duration of action

  摘要：

  We have prepared a series of cis-4-(tetrazolylalkyl)piperidine-2-carboxylic acids as potent and selective N-methyl-D-aspartic acid (NMDA) receptor antagonists. NMDA antagonists may prove to be useful therapeutic agents, for instance, as anticonvulsants, in the treatment of neurodegenerative disorders such as Alzheimer's disease and in the prevention of neuronal damage that occurs during cerebral ischemia. The compounds prepared were evaluated in vitro in both receptor binding assays ([H-3]CGS-19755, [H-3]AMPA, and [H-3]kainic acid) and in a cortical-wedge preparation (versus NMDA, quisqualic acid, and kainic acid) to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced convulsions in neonatal rats and NMDA-induced lethality in mice. The most potent compound of this series, 15 (LY233053), selectively displaced [H-3]CGS-19755 binding with an IC50 of 107 +/- 7 nM and selectively antagonized responses due to NMDA in a cortical-wedge preparation with an IC50 of 4.2 +/- 0.4-mu-M. Compound 15 blocked both NMDA-induced convulsions in neonatal rats (minimum effective dose (MED) = 20 mg/kg ip) and NMDA-induced lethality in mice (MED = 5 mg/kg ip). This is the first example of an NMDA receptor antagonist that incorporates a tetrazole moiety as an omega-acid bioisostere. These amino acid antagonists are also unique from their phosphonic acid counterparts in that they have a shorter duration of action in vivo. For the treatment of acute disorders such as stroke, where an NMDA antagonist would be administered parenterally, the shorter duration of action may be beneficial, e.g., allowing for better dosage control. The combination of potent NMDA receptor antagonism and a short duration of action may make these compounds useful therapeutic agents in the treatment of a variety of neurological disorders.

  DOI：

  10.1021/jm00105a016

文献信息

• Novel herbicides
  申请人：——

  公开号：US20020156285A1

  公开（公告）日：2002-10-24

  Compounds of formula 1 1 R 1 is hydrogen, fluorine, chlorine, bromine or methyl; R 2 is C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 halogenalkoxy, nitro, amino or cyano; 2 R 3 , R 15 to R 39 and X 6 to X 19 are as defined in claim 1, and the agrochemically acceptable salts and stereoisomers of these compounds of formula I are suitable for use as herbicides.

  化合物的公式为11R1，其中R1是氢，氟，氯，溴或甲基；R2是C1-C4烷基，C1-C4卤代烷基，卤素，羟基，C1-C4烷氧基，C1-C4卤代烷氧基，硝基，氨基或氰基；2R3，R15到R39和X6到X19如权利要求1所定义，并且这些公式I的化合物的农药可接受盐和立体异构体适用于作为除草剂使用。
• ORNSTEIN, PAUL L.;SCHOEPP, DARRYLE D.;ARNOLD, M. BRIAN;LEANDER, J. DAVID;+, J. MED. CHEM., 34,(1991) N, C. 90-97
  作者：ORNSTEIN, PAUL L.、SCHOEPP, DARRYLE D.、ARNOLD, M. BRIAN、LEANDER, J. DAVID、+

  DOI：——

  日期：——
• N-HETEROARYL-SUBSTITUTED PYRIDINE DERIVATIVES AND THEIR USE AS HERBICIDES
  申请人：Novartis AG

  公开号：EP1076656A2

  公开（公告）日：2001-02-21
• US6369002B1
  申请人：——

  公开号：US6369002B1

  公开（公告）日：2002-04-09
• [EN] NOVEL HERBICIDES<br/>[FR] NOUVEAUX HERBICIDES
  申请人：——

  公开号：WO1999055693A2

  公开（公告）日：1999-11-04

  [EN] Compounds of formula (I), wherein A = N- or (a); R1 is hydrogen, fluorine, chlorine, bromine or methyl; R2 is C1-C4alkyl, C1-C4halogenalkyl, halogen, hydroxy, C1-C4alkoxy, C1-C4halogenalkoxy, nitro, amino or cyano; W is a (W1), (W2), (W3), (W4), (W5), (W6), (W7), (W8), (W9) or (W10) group; and R3, R15 to R39 and X6 to X19 are as defined in claim 1, and the agrochemically acceptable salts and stereoisomers of these compounds of formula (I) are suitable for use as herbicides.
  [FR] L'invention concerne les composés selon la formule (I) dans laquelle A = N- ou (a); R1 représente hydrogène, fluor, chlore, brome ou méthyle; R2 représente alkyle C1-C4, halogénalkyle C1-C4, halogène, hydroxy, alcoxy C1-C4, halogénalcoxy C1-C4, nitro, amino ou cyano. W représente (W1), (W2), (W3), (W4), (W5), (W6), (W7), (W8), (W9) ou (W10); et R3, R15 à R39 et X6 à X19 sont tels que définis dans la revendication 1. L'invention traite également de sels agrochimiquement acceptables et de stéréoisomères de ces composés selon la formule (I) qui peuvent être utilisés comme herbicides.