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ethyl (3R,4S)-4-(benzylamino)-3-methoxypiperidine-1-carboxylate | 907543-85-5

中文名称
——
中文别名
——
英文名称
ethyl (3R,4S)-4-(benzylamino)-3-methoxypiperidine-1-carboxylate
英文别名
Cis(+)ethyl 4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate;ethyl (3R,4S)-3-methoxy-4-(phenylmethoxycarbonylamino)piperidine-1-carboxylate
ethyl (3R,4S)-4-(benzylamino)-3-methoxypiperidine-1-carboxylate化学式
CAS
907543-85-5
化学式
C17H24N2O5
mdl
——
分子量
336.388
InChiKey
UXGDGFBLMNWNBF-LSDHHAIUSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    1.8
  • 重原子数:
    24
  • 可旋转键数:
    7
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.53
  • 拓扑面积:
    77.1
  • 氢给体数:
    1
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    ethyl (3R,4S)-4-(benzylamino)-3-methoxypiperidine-1-carboxylate 在 palladium on activated charcoal 、 氢气 、 sodium hydride 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下, 以 四氢呋喃乙醇N,N-二甲基甲酰胺 为溶剂, 生成
    参考文献:
    名称:
    新型GPR119激动剂的发现,优化和体内评估
    摘要:
    GPR119越来越被视为治疗II型糖尿病和代谢综合征其他成分的有吸引力的靶标。在一项旨在开发GPR119受体激动剂的计划中,我们鉴定了具有降低hERG抑制作用的有效化合物,具有良好的药代动力学特性以及在体内具有出色的降糖效果的化合物。但是,在GPR119敲除(KO)小鼠模型中进行的进一步分析显示,其生物学效应并不完全是由于GPR119激动作用,这突出了转基因动物在药物发现计划中的价值。
    DOI:
    10.1016/j.bmcl.2011.10.033
  • 作为产物:
    描述:
    3,4,4-三甲氧基哌啶-1-羧酸乙酯硫酸 、 palladium 10% on activated carbon 、 甲酸铵三乙酰氧基硼氢化钠碳酸氢钠 作用下, 以 四氢呋喃甲醇 为溶剂, 反应 16.5h, 生成 ethyl (3R,4S)-4-(benzylamino)-3-methoxypiperidine-1-carboxylate
    参考文献:
    名称:
    Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099)
    摘要:
    AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.
    DOI:
    10.1021/jm500462x
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文献信息

  • ANTIBACTERIAL PIPERDINE DERIVATIVES
    申请人:Basarab Gregory
    公开号:US20100179150A1
    公开(公告)日:2010-07-15
    Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.
    描述了化学式(I)的化合物及其药学上可接受的盐。描述了制备它们的过程,含有它们的药物组合物,它们作为药物的用途以及它们在治疗细菌感染中的用途。
  • CHEMICAL COMPOUNDS
    申请人:AstraZeneca, Intellectual Property
    公开号:US20130150366A1
    公开(公告)日:2013-06-13
    Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use in the treatment of bacterial infections are also described.
    本文描述了化学式(I)的化合物及其药学上可接受的盐。还描述了制备它们的过程、含有它们的制药组合物,以及它们在治疗细菌感染方面的用途。
  • Antibacterial piperdine derivatives
    申请人:Basarab Gregory
    公开号:US08399489B2
    公开(公告)日:2013-03-19
    Compounds of formula (I) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.
    本文描述了公式(I)的化合物及其药学上可接受的盐。同时还描述了它们的制备过程、包含它们的药物组合物、它们作为药物的用途以及它们在治疗细菌感染方面的应用。
  • Optimization of Pyrrolamide Topoisomerase II Inhibitors Toward Identification of an Antibacterial Clinical Candidate (AZD5099)
    作者:Gregory S. Basarab、Pamela J. Hill、C. Edwin Garner、Ken Hull、Oluyinka Green、Brian A. Sherer、P. Brian Dangel、John I. Manchester、Shanta Bist、Sheila Hauck、Fei Zhou、Maria Uria-Nickelsen、Ruth Illingworth、Richard Alm、Mike Rooney、Ann E. Eakin
    DOI:10.1021/jm500462x
    日期:2014.7.24
    AZD5099 (compound 63) is an antibacterial agent that entered phase 1 clinical trials targeting infections caused by Gram-positive and fastidious Gram-negative bacteria. It was derived from previously reported pyrrolamide antibacterials and a fragment-based approach targeting the ATP binding site of bacterial type II topoisomerases. The program described herein varied a 3-piperidine substituent and incorporated 4-thiazole substituents that form a seven-membered ring intramolecular hydrogen bond with a 5-position carboxylic acid. Improved antibacterial activity and lower in vivo clearances were achieved. The lower clearances were attributed, in part, to reduced recognition by the multidrug resistant transporter Mrp2. Compound 63 showed notable efficacy in a mouse neutropenic Staphylococcus aureus infection model. Resistance frequency versus the drug was low, and reports of clinical resistance due to alteration of the target are few. Hence, 63 could offer a novel treatment for serious issues of resistance to currently used antibacterials.
  • Discovery, optimisation and in vivo evaluation of novel GPR119 agonists
    作者:Katy J. Brocklehurst、Anders Broo、Roger J. Butlin、Hayley S. Brown、David S. Clarke、Öjvind Davidsson、Kristin Goldberg、Sam D. Groombridge、Elizabeth E. Kelly、Andrew Leach、Darren McKerrecher、Charles O’Donnell、Simon Poucher、Paul Schofield、James S. Scott、Joanne Teague、Leanne Westgate、Matt J.M. Wood
    DOI:10.1016/j.bmcl.2011.10.033
    日期:2011.12
    GPR119 is increasingly seen as an attractive target for the treatment of type II diabetes and other elements of the metabolic syndrome. During a programme aimed at developing agonists of the GPR119 receptor, we identified compounds that were potent with reduced hERG liabilities, that had good pharmacokinetic properties and that displayed excellent glucose-lowering effects in vivo. However, further
    GPR119越来越被视为治疗II型糖尿病和代谢综合征其他成分的有吸引力的靶标。在一项旨在开发GPR119受体激动剂的计划中,我们鉴定了具有降低hERG抑制作用的有效化合物,具有良好的药代动力学特性以及在体内具有出色的降糖效果的化合物。但是,在GPR119敲除(KO)小鼠模型中进行的进一步分析显示,其生物学效应并不完全是由于GPR119激动作用,这突出了转基因动物在药物发现计划中的价值。
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