摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

(2R,3S)-ethyl 3-(piperidin-1-ylmethyl)oxirane-2-carboxylate | 1207983-19-4

中文名称
——
中文别名
——
英文名称
(2R,3S)-ethyl 3-(piperidin-1-ylmethyl)oxirane-2-carboxylate
英文别名
ethyl (2R,3S)-3-(piperidin-1-ylmethyl)oxirane-2-carboxylate
(2R,3S)-ethyl 3-(piperidin-1-ylmethyl)oxirane-2-carboxylate化学式
CAS
1207983-19-4
化学式
C11H19NO3
mdl
——
分子量
213.277
InChiKey
FQKWDOPAJMGHSH-VHSXEESVSA-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):
    1.1
  • 重原子数:
    15
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.91
  • 拓扑面积:
    42.1
  • 氢给体数:
    0
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    (2R,3S)-ethyl 3-(piperidin-1-ylmethyl)oxirane-2-carboxylate 在 potassium hydroxide 作用下, 以 乙醇 为溶剂, 以83%的产率得到potassium (2R,3S)-3-(piperidin-1-ylmethyl)oxirane-2-carboxylate
    参考文献:
    名称:
    Novel Irreversible Epidermal Growth Factor Receptor Inhibitors by Chemical Modulation of the Cysteine-Trap Portion
    摘要:
    Irreversible EGFR inhibitors can circumvent acquired resistance to first-generation reversible, ATP-competitive inhibitors in the treatment of non-small-cell lung cancer. They contain both a driver group, which assures target recognition, and it warhead, generally an acrylamide or propargylamide fragment that binds covalently to Cys797 within the kinase domain of EGFR. We performed it systematic exploration of the role for the warhead group, introducing different cysteine-trapping fragments at position 6 of a traditional 4-anilinoquinazoline scaffold. We found that different reactive groups, including epoxyamides (compounds 3-6) and phenoxyacetamides (compounds 7-9), were able to irreversibly inhibit EGFR. In particular, at significant lower concentrations than gefitinib (1), (2R,3R)-N-(4-(3-bromoanilino)quinazolin-6-yl)-3-(piperidin-1-ylmethyl)oxirane-2-carboxamide (6) inhibited EGFR autophosphorylation and downstream Signaling pathways, Suppressed proliferation, and induced apoptosis in gefitinib-resistant NSCLC H 1975 cells, harboring the T790M mutation in EGFR.
    DOI:
    10.1021/jm901558p
  • 作为产物:
    描述:
    (2R,3R)-二乙基-2,3-环氧琥珀酸 在 sodium tetrahydroborate 、 乙醇三乙胺 作用下, 以 二氯甲烷 为溶剂, 反应 28.25h, 生成 (2R,3S)-ethyl 3-(piperidin-1-ylmethyl)oxirane-2-carboxylate
    参考文献:
    名称:
    [EN] PYRIDOPYRIMIDINE DERIVATIVES USEFUL AS KRAS G12C AND KRAS G12D INHIBITORS IN THE TREATMENT OF CANCER
    [FR] DÉRIVÉS DE PYRIDOPYRIMIDINE UTILES EN TANT QU'INHIBITEURS DE KRAS G12C ET DE KRAS G12D DANS LE TRAITEMENT DU CANCER
    摘要:
    本文提供了KRAS G12C和KRAS G12D抑制剂,其组成,以及使用这些抑制剂的方法。这些抑制剂对治疗多种疾病有用,包括胰腺癌、结直肠癌和肺癌。
    公开号:
    WO2021081212A1
点击查看最新优质反应信息

文献信息

  • [EN] PYRIDOPYRIMIDINE DERIVATIVES USEFUL AS KRAS G12C AND KRAS G12D INHIBITORS IN THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE PYRIDOPYRIMIDINE UTILES EN TANT QU'INHIBITEURS DE KRAS G12C ET DE KRAS G12D DANS LE TRAITEMENT DU CANCER
    申请人:AMGEN INC
    公开号:WO2021081212A1
    公开(公告)日:2021-04-29
    Provided herein are KRAS G12C and KRAS G12D inhibitors, composition of the same, and methods of using the same. These inhibitors are useful for treating a number of disorders, including pancreatic, colorectal, and lung cancers.
    本文提供了KRAS G12C和KRAS G12D抑制剂,其组成,以及使用这些抑制剂的方法。这些抑制剂对治疗多种疾病有用,包括胰腺癌、结直肠癌和肺癌。
  • Novel Irreversible Epidermal Growth Factor Receptor Inhibitors by Chemical Modulation of the Cysteine-Trap Portion
    作者:Caterina Carmi、Andrea Cavazzoni、Stefano Vezzosi、Fabrizio Bordi、Federica Vacondio、Claudia Silva、Silvia Rivara、Alessio Lodola、Roberta R. Alfieri、Silvia La Monica、Maricla Galetti、Andrea Ardizzoni、Pier Giorgio Petronini、Marco Mor
    DOI:10.1021/jm901558p
    日期:2010.3.11
    Irreversible EGFR inhibitors can circumvent acquired resistance to first-generation reversible, ATP-competitive inhibitors in the treatment of non-small-cell lung cancer. They contain both a driver group, which assures target recognition, and it warhead, generally an acrylamide or propargylamide fragment that binds covalently to Cys797 within the kinase domain of EGFR. We performed it systematic exploration of the role for the warhead group, introducing different cysteine-trapping fragments at position 6 of a traditional 4-anilinoquinazoline scaffold. We found that different reactive groups, including epoxyamides (compounds 3-6) and phenoxyacetamides (compounds 7-9), were able to irreversibly inhibit EGFR. In particular, at significant lower concentrations than gefitinib (1), (2R,3R)-N-(4-(3-bromoanilino)quinazolin-6-yl)-3-(piperidin-1-ylmethyl)oxirane-2-carboxamide (6) inhibited EGFR autophosphorylation and downstream Signaling pathways, Suppressed proliferation, and induced apoptosis in gefitinib-resistant NSCLC H 1975 cells, harboring the T790M mutation in EGFR.
查看更多