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N-2-(5-bromopyridyl)aminomethyldiphosphonic acid

中文名称
——
中文别名
——
英文名称
N-2-(5-bromopyridyl)aminomethyldiphosphonic acid
英文别名
[(5-bromopyridinium-2-ylamino)-(phosphono)methyl]phosphonate;[[(5-bromo-2-pyridinyl)amino]methylene]-1,1-bisphosphonate;N-(5-bromopyrid-2-yl)aminomethylenebisphosphonic acid;(5-bromopyridin-2-ylamino)methylenebisphosphonic acid;[(5-Bromopyridinium-2-ylamino)(phosphono)methyl]phosphonate;[(R)-[(5-bromopyridin-1-ium-2-yl)amino]-phosphonomethyl]-hydroxyphosphinate
N-2-(5-bromopyridyl)aminomethyldiphosphonic acid化学式
CAS
——
化学式
C6H9BrN2O6P2
mdl
——
分子量
346.999
InChiKey
QMTRPEYMFKONLX-UHFFFAOYSA-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):
    -1.5
  • 重原子数:
    17
  • 可旋转键数:
    4
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.17
  • 拓扑面积:
    140
  • 氢给体数:
    5
  • 氢受体数:
    8

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    吡啶基侧链碱度与 5-卤素取代的(吡啶-2-基)氨基甲烷-1,1-二膦酸的 Z/E 偏好之间关系的 X 射线证据;对溶液中金属离子配位的影响
    摘要:
    三种盐(1-a-3-a)的晶体结构,5-氯(1)、5溴(2)和5-碘(3)取代(吡啶-2-基)氨基甲烷-1反应的产物,1-二膦酸和 4-氨基吡啶通过单晶 X 射线衍射测定,并讨论了分子几何形状和固态组织。在所有 1-a-3-a 中,与母体两性离子相比,双膦酸二价阴离子在 C2 -N1 键方面采用相反的 (E) 构象。这提供了进一步的证据,即涉及环外和吡啶鎓 N 原子作为质子供体和膦酸/膦酸酯基团的 O 原子作为受体的分子间 N−H…O 氢键在稳定这种特殊的 Z 构象方面起着重要作用。酸的亚类。还研究了 [(5-iodopyridin-2-yl)amino]methane-1,1-diphosphonic acid (3) 的溶液行为和络合物形成能力。化合物 3 以 Z/E 混合物的形式存在于溶液中。然而,与 1 和 2 相比,3 中围绕 C2 -N1 键旋转的障碍较低。这对于 Zn(II)、Mg(II)
    DOI:
    10.3998/ark.5550190.0013.412
  • 作为产物:
    描述:
    N-(5-bromopyridin-2-yl)formamide甲醇三氟甲磺酸三甲基硅酯 作用下, 以 乙醚二氯甲烷 为溶剂, 20.0 ℃ 、66.66 Pa 条件下, 生成 N-2-(5-bromopyridyl)aminomethyldiphosphonic acid
    参考文献:
    名称:
    的新合成的官能化的芳基和吡啶基酸氨基亚甲基和它们的衍生物通过硅辅助方法
    摘要:
    通过硅辅助方法已经开发了新的方便的合成官能化的芳基和吡啶基氨基亚甲基双膦酸及其衍生物的方法。利用亚磷酸三(三甲基甲硅烷基)酯与N的独特反应,获得了含有吡啶部分的新功能化氨基亚甲基双膦酸-甲酰基氨基吡啶和三氟甲磺酸三甲基甲硅烷基酯在温和条件下作为催化剂。中间体–形成的四(三甲基甲硅烷基)氨基亚甲基双膦酸酯通过用过量甲醇进一步处理而转化为目标酸。相反,在氯化锌催化剂的存在下,在加热(130℃)下,将四种组分的混合物(亚磷酸二乙基三甲基甲硅烷基酯,原甲酸三乙基酯,芳基或吡啶基胺和亚磷酸二乙基酯)合成相应的四乙基氨基亚甲基双膦酸酯。提出并详细讨论了目标物质形成的催化方案。
    DOI:
    10.1016/j.jorganchem.2020.121177
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文献信息

  • HETEROCYCLYL-PYRIDINYL-BASED BIPHOSPHONIC ACID, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, COMPOSITION THEREOF AND METHOD OF USE THEREOF
    申请人:Tsantrizos Youla S.
    公开号:US20130203702A1
    公开(公告)日:2013-08-08
    The present invention relates to novel compounds, compositions containing same and methods for inhibiting human farnesyl pyrophosphate synthase or for the treatment or prevention of disease conditions using said compounds;
    本发明涉及新型化合物、含有该化合物的组合物以及使用该化合物抑制人类法尼醇焦磷酸合酶或治疗或预防疾病状况的方法;
  • Effects of Bisphosphonates on the Growth of <i>Entamoeba histolytica</i> and <i>Plasmodium </i>Species in Vitro and in Vivo
    作者:Subhash Ghosh、Julian M. W. Chan、Christopher R. Lea、Gary A. Meints、Jared C. Lewis、Zev S. Tovian、Ryan M. Flessner、Timothy C. Loftus、Iris Bruchhaus、Howard Kendrick、Simon L. Croft、Robert G. Kemp、Seiki Kobayashi、Tomoyoshi Nozaki、Eric Oldfield
    DOI:10.1021/jm030084x
    日期:2004.1.1
    The effects of a series of 102 bisphosphonates on the inhibition of growth of Entamoeba histolytica and Plasmodium falciparum in vitro have been determined, and selected compounds were further investigated for their in vivo activity. Forty-seven compounds tested were active (IC50 < 200 muM) versus E. histolytica growth in vitro. The most active compounds (IC50 similar to 4-9 muM) were nitrogen-containing bisphosphonates with relatively large aromatic side chains. Simple n-alkyl-1-hydroxy-1,1-bisphosphonates, known inhibitors of the enzyme farnesylpyrophosphate (FPP) synthase, were also active, with optimal activity being found with C9-C10 side chains. However, numerous other nitrogen-containing bisphosphonates known to be potent FPP synthase inhibitors, such as risedronate or pamidronate, had little or no activity. Several pyridine-derived bisphosphonates were quite active (IC50 similar to 10-20 muM), and this activity was shown to correlate with the basicity of the aromatic group, with activity decreasing with increasing pK(a) values. The activities of all compounds were tested versus a human nasopharyngeal carcinoma (KB) cell line to enable an estimate of the therapeutic index (TI). Five bisphosphonates were selected and then screened for their ability to delay the development of amebic liver abscess formation in an E. histolytica infected hamster model. Two compounds were found to decrease liver abscess formation at 10 mg/kg ip with little or no effect on normal liver mass. With P. falciparum, 35 compounds had IC50 values <200 muM in an in vitro assay. The most active compounds were also simple n-alkyl-1-hydroxy-1,1-bisphosphonates, having IC50 values around 1 muM. Five compounds were again selected for in vivo investigation in a Plasmodium berghei ANKA BALB/c mouse suppressive test. The most active compound, a C9 n-alkyl side chain containing bisphosphonate, caused an 80% reduction in parasitemia with no overt toxicity. Taken together, these results show that bisphosphonates appear to be useful lead compounds for the development of novel antiamebic and antimalarial drugs.
  • US8816082B2
    申请人:——
    公开号:US8816082B2
    公开(公告)日:2014-08-26
  • US9290526B2
    申请人:——
    公开号:US9290526B2
    公开(公告)日:2016-03-22
  • Synthesis of new functionalized aryl and pyridyl aminomethylenebisphosphonic acids and their derivatives via silicon-assisted methodology
    作者:Andrey A. Prishchenko、Roman S. Alekseyev、Mikhail V. Livantsov、Olga P. Novikova、Ludmila I. Livantsova、Valery S. Petrosyan
    DOI:10.1016/j.jorganchem.2020.121177
    日期:2020.4
    The new convenient synthesis of functionalized aryl and pyridyl aminomethylenebisphosphonic acids and their derivatives has been developed via silicon-assisted methodology. New functionalized aminomethylenebisphosphonic acids containing pyridines moieties were obtained using unique reaction of tris(trimethylsilyl) phosphite with N-formyl aminopyridines and trimethylsilyl triflate as a catalyst under
    通过硅辅助方法已经开发了新的方便的合成官能化的芳基和吡啶基氨基亚甲基双膦酸及其衍生物的方法。利用亚磷酸三(三甲基甲硅烷基)酯与N的独特反应,获得了含有吡啶部分的新功能化氨基亚甲基双膦酸-甲酰基氨基吡啶和三氟甲磺酸三甲基甲硅烷基酯在温和条件下作为催化剂。中间体–形成的四(三甲基甲硅烷基)氨基亚甲基双膦酸酯通过用过量甲醇进一步处理而转化为目标酸。相反,在氯化锌催化剂的存在下,在加热(130℃)下,将四种组分的混合物(亚磷酸二乙基三甲基甲硅烷基酯,原甲酸三乙基酯,芳基或吡啶基胺和亚磷酸二乙基酯)合成相应的四乙基氨基亚甲基双膦酸酯。提出并详细讨论了目标物质形成的催化方案。
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同类化合物

(1-氨基丁基)磷酸 顺丙烯基磷酸 除草剂BUMINAFOS 阿仑膦酸 阻燃剂 FRC-1 铵甲基膦酸盐 钠甲基乙酰基膦酸酯 钆1,5,9-三氮杂环十二烷-N,N',N''-三(亚甲基膦酸) 钆-1,4,7-三氮杂环壬烷-N,N',N''-三(亚甲基膦酸) 重氮甲基膦酸二乙酯 辛基膦酸二丁酯 辛基膦酸 辛基-膦酸二钾盐 辛-1-烯-2-基膦酸 试剂12-Azidododecylphosphonicacid 英卡膦酸 苯胺,4-乙烯基-2-(1-甲基乙基)- 苯甲基膦酸二甲酯 苯基膦酸二甲酯 苯基膦酸二仲丁酯 苯基膦酸二乙酯 苯基膦酸二乙酯 苯基磷酸二辛酯 苯基二异辛基亚磷酸酯 苯基(1H-1,2,4-三唑-1-基)甲基膦酸二乙酯 苯丁酸,b-氨基-g-苯基- 苄基膦酸苄基乙酯 苄基亚甲基二膦酸 膦酸,[(2-乙基己基)亚氨基二(亚甲基)]二,triammonium盐(9CI) 膦酸叔丁酯乙酯 膦酸单十八烷基酯钾盐 膦酸二辛酯 膦酸二(二十一烷基)酯 膦酸,辛基-,单乙基酯 膦酸,甲基-,单(2-乙基己基)酯 膦酸,甲基-,二(苯基甲基)酯 膦酸,甲基-,2-甲氧基乙基1-甲基乙基酯 膦酸,丁基乙基酯 膦酸,[苯基[(苯基甲基)氨基]甲基]-,二甲基酯 膦酸,[[羟基(苯基甲基)氨基]苯基甲基]-,二(苯基甲基)酯 膦酸,[2-(环丙基氨基)-2-羰基乙基]-,二乙基酯 膦酸,[2-(二甲基亚肼基)丙基]-,二乙基酯,(E)- 膦酸,[1-甲基-2-(苯亚氨基)乙烯基]-,二乙基酯 膦酸,[1-(乙酰基氨基)-1-甲基乙基]-(9CI) 膦酸,[(环己基氨基)苯基甲基]-,二乙基酯 膦酸,[(二乙氧基硫膦基)(二甲氨基)甲基]- 膦酸,[(2S)-2-氨基-2-苯基乙基]-,二乙基酯 膦酸,[(1Z)-2-氨基-2-(2-噻嗯基)乙烯基]-,二乙基酯 膦酸,P-[(二乙胺基)羰基]-,二乙基酯 膦酸,(氨基二环丙基甲基)-