2-bromo-1,4-bis(diethylphosphonato)xylene | 346691-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-1,4-bis(diethylphosphonato)xylene
• 英文别名: tetraethyl (2-bromo-1,4-phenylene)bis(methylene)diphosphonate；Tetraethyl 2-bromo-alpha,alpha'-p-xylenebisphosphonate；2-bromo-1,4-bis(diethoxyphosphorylmethyl)benzene
• CAS: 346691-69-8
• 化学式: C₁₆H₂₇BrO₆P₂
• 分子量: 457.238
• InChiKey: HXMJUEDHULEGGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-bromo-1,4-bis(diethylphosphonato)xylene 在 吡啶 、 四(三苯基膦)钯 、 sodium methylate 、 三溴化硼 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (E,E)-2,5-bis(4’-acetoxy-3’-carbomethoxystyryl)-1-tri-n-butylstannylbenzene
  参考文献：
  名称：

  Tritium-labeled (E,E)-2,5-bis(4′-hydroxy-3′-carboxystyryl)benzene as a probe for β-amyloid fibrils

  摘要：

  Accumulation of A beta in the brains of Alzheimer disease (AD) patients reflects an imbalance between A beta production and clearance from their brains. Alternative cleavage of amyloid precursor protein (APP) by processing proteases generates soluble APP fragments including the neurotoxic amyloid A beta 40 and A beta 42 peptides that assemble into fibrils and form plaques. Plaque-buildup occurs over an extended time-frame, and the early detection and modulation of plaque formation are areas of active research. Radiolabeled probes for the detection of amyloid plaques and fibrils in living subjects are important for noninvasive evaluation of AD diagnosis, progression, and differentiation of AD from other neurode-generative diseases and age-related cognitive decline. Tritium-labeled (E, E)-1-[H-3]-2,5-bis(4'-hydroxy-3'-carbomethoxystyryl)benzene possesses an improved level of chemical stability relative to a previously reported radioiodinated analog for radiometric quantification of A beta plaque and tau pathology in brain tissue and in vitro studies with synthetic A beta and tau fibrils. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.075
• 作为产物：
  描述：

  甲苄基溴 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 生成 2-bromo-1,4-bis(diethylphosphonato)xylene
  参考文献：
  名称：

  Tritium-labeled (E,E)-2,5-bis(4′-hydroxy-3′-carboxystyryl)benzene as a probe for β-amyloid fibrils

  摘要：

  Accumulation of A beta in the brains of Alzheimer disease (AD) patients reflects an imbalance between A beta production and clearance from their brains. Alternative cleavage of amyloid precursor protein (APP) by processing proteases generates soluble APP fragments including the neurotoxic amyloid A beta 40 and A beta 42 peptides that assemble into fibrils and form plaques. Plaque-buildup occurs over an extended time-frame, and the early detection and modulation of plaque formation are areas of active research. Radiolabeled probes for the detection of amyloid plaques and fibrils in living subjects are important for noninvasive evaluation of AD diagnosis, progression, and differentiation of AD from other neurode-generative diseases and age-related cognitive decline. Tritium-labeled (E, E)-1-[H-3]-2,5-bis(4'-hydroxy-3'-carbomethoxystyryl)benzene possesses an improved level of chemical stability relative to a previously reported radioiodinated analog for radiometric quantification of A beta plaque and tau pathology in brain tissue and in vitro studies with synthetic A beta and tau fibrils. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.075

文献信息

• Materials, methods, and uses for photochemical generation of acids and/or radical species
  申请人：Marder Seth

  公开号：US20050173683A1

  公开（公告）日：2005-08-11

  The present invention provides compounds and compositions, which include: at least one chromophore having strong simultaneous two-photon or multi-photon absorptivity; at least one acid- or radical-generator in close proximity to the chromophore; such that the single- or multi-photon excitation of the chromophore results in the generation of an acid and/or redical that is capable of activating chemistry; and such that compositions of matter based on the componds and compositions of the invention can be photo-patterned by one- or multiphoton excitation.

  本发明提供了化合物和组合物，其中包括：至少一种具有强烈的同时双光子或多光子吸收性的色团；至少一个与色团相邻的酸或自由基发生剂；这样，色团的单光子或多光子激发会产生能够激活化学反应的酸和/或自由基；并且基于该发明的化合物和组合物的物质组成可以通过单光子或多光子激发进行光图案化。
• Materials, methods and uses for photochemical generation of acids and/or radical species
  申请人：The Arizona Board of Regents on behalf of the University of Arizona

  公开号：EP2236488A1

  公开（公告）日：2010-10-06

  The present invention provides compounds and compositions, including a selenonium or sulfonium group, which include; at least one chromophore having strong simultaneous two-photon or multi-photon absorptivity; at least one acid- or radical-generator in close proximity to the chromophore; such that the single- or multi-photon excitation of the chromophore results in the generation of an acid and/or radical that is capable of activating chemistry; and such that compositions of matter based on the compounds and compositions of the invention can be photo-patterned by one- or multi-photon excitation.

  本发明提供了包括硒基或锍基团的化合物和组合物，其中包括：至少一个具有强同步双光子或多光子吸收性的发色团；至少一个靠近发色团的酸或自由基发生器；这样，发色团的单光子或多光子激发会导致产生能够激活化学反应的酸和/或自由基；并且，基于本发明化合物和组合物的物质组合物可以通过单光子或多光子激发进行光图案化。
• Radioiodinated Styrylbenzenes and Thioflavins as Probes for Amyloid Aggregates
  作者：Z.-P. Zhuang、M.-P. Kung、C. Hou、D. M. Skovronsky、T. L. Gur、K. Plössl、J. Q. Trojanowski、V. M.-Y. Lee、H. F. Kung

  DOI：10.1021/jm010045q

  日期：2001.6.1

  We report for the first time that small molecule-based radiodiodinated ligands, showing selective binding to A beta aggregates, cross the intact blood-brain barrier by simple diffusion. Four novel ligands showing preferential labeling of amyloid aggregates of A beta (1-40) and A beta (1-42) peptides, commonly associated with plaques in the brain of people with Alzheimer's disease (AD), were developed. Two I-125-labeled styrylbenzenes, (E,E)-1-iodo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)-styrylbenzene, 12 (ISB), and (E,E)-1-iodo-2,5-bis(3-hydroxycarbonyl-4-methoxy)styrylbenzene, 13 (IMSB), and two I-125-labeled thioflavins, 2-[4 '-(dimethylamino)phenyl]-6-iodobenzothiazole, 18a (TZDM), and 2- [4 '-(4 " -methylpiperazin-1-yl)phenyl]-6-iodobenzothiazole, 18b (TZPI), were prepared at a high specific activity (2200 Ci/mmol). In vitro binding studies of these ligands showed excellent binding affinities with K-d values of 0.08, 0.13, 0.06, and 0.13 nM for aggregates of A beta (1-40) and 0.15, 0.73, 0.14, and 0.15 nM for aggregates of A beta (1-42), respectively. Interestingly, under a competitive-binding assaying condition, different binding sites on A beta (1-40) and A beta (1-42) aggregates, which are mutually exclusive, were observed for styrylbenzenes and thioflavins. Autoradiography studies of postmortem brain sections of a patient with Down's syndrome known to contain primarily A beta (1-42) aggregates in the brain showed that both [I-125]18a and [I-125]18b labeled these brain sections, but [I-125]13, selective for A beta (1-40) aggregates, exhibited very low labeling of the comparable brain section. Biodistribution studies in normal mice after an iv injection showed that [I-125]18a and [I-125]18b exhibited excellent brain uptake and retention, the levels of which were much higher than those of [I-125]12 and [I-125]13. These findings strongly suggest that the new radioiodinated ligands, [I-125]12 (ISB), [I-125]13 (IMSB), [I-125]18a, (TZDM), and [I-125]18b (TZPI), may be useful as biomarkers for studying A beta (1-40) as well as A beta (1-42) aggregates of amyloidogenesis in AD patients.
• Zhuang, Z.-P.; Kung, M.-P.; Hou, C., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S236 - S238
  作者：Zhuang, Z.-P.、Kung, M.-P.、Hou, C.、Lee, C.-W.、Trojanowski, J. Q.、Lee, V. M.-Y.、Kung, H. F.

  DOI：——

  日期：——
• US7459106B2
  申请人：——

  公开号：US7459106B2

  公开（公告）日：2008-12-02